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  • 1.
    Baryshnikov, Gleb V.
    et al.
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology. Tomsk State University, Russian Federation.
    Valiev, Rashid R.
    Minaev, Boris F.
    Ågren, Hans
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology. Siberian Federal University, Russian Federation.
    Optical tuning of tetrabenzo[8]circulene derivatives through pseudorotational conformational isomerization2018In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 151, p. 372-379Article in journal (Refereed)
    Abstract [en]

    In order to further search efficient [8]circulene materials for OLED applications we have theoretically investigated the structure and electronic, absorption spectra of functionalized tetrabenzo[8]circulenes with different substituents in the outer perimeter. These hydrocarbon materials complement the wide family of [8]circulenes which earlier have been demonstrated to possess promising emissive and exciplex-forming properties suitable for organic light emitting diodes. The hydrocarbon tetrabenzo[8]circulenes show saddle shape of the molecular skeleton which can exist in two different conformations with different curvatures of the macrocycle. The aromaticity, electronic structure and orbital pattern are found to be principally different for these two isomers, where the global minimum isomer is weakly antiaromatic and electronically less stable comparing with the non-aromatic local minimum structure. The absorption spectra are also very different: the global minimum structure is more active in the long-wavelength region while the local minimum isomer shows absorption only at short wavelengths. Our computational findings suggest a new concept for optical tuning of curved [8]circulenes through conformational isomerization and aromaticity control, thus through structural variations without changing the molecular composition. Based on this principle we have designed novel functionalized [8]circulenes with promising fluorescence activity.

  • 2. Bu, L.
    et al.
    Chen, J.
    Wei, X.
    Li, Xin
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Ågren, Hans
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Xie, Y.
    An AIE and ICT based NIR florescent probe for cysteine and homocysteine2017In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 136, p. 724-731Article in journal (Refereed)
    Abstract [en]

    A combination of aggregation-induced emission and intramolecular charge transfer was achieved by using a triphenylamine analogue and a dicyanovinyl moiety as the electron donating and accepting units, respectively. Hence, we designed and synthesized a probe with a D-π-A framework as a near-infrared fluorescence turn-on probe for biothiols (cysteine and homocysteine). Owing to the remarkable intramolecular charge transfer effect as well as intramolecular rotations associated with the donor moiety, the probe exhibits extremely weak fluorescence, which becomes a good starting point for developing fluorescence “turn-on” probes. Upon reaction with cysteine or homocysteine utilizing the dicyanovinyl moiety, the intramolecular charge transfer character was weakened, and the reacting products were observed to aggregate in aqueous solutions, resulting in the aggregation-induced emission effect with red fluorescence at 651 and 656 nm, respectively. Hence, the probe could be used as a fluorescence “turn-on” sensor for cysteine and homocysteine, with the sensing time of less than 4 min and the detection limits of 8.4 μM and 5.7 μM towards cysteine and homocysteine, respectively. The probe could distinguish cysteine and homocysteine from glutathione. The sensing mechanism was systematically investigated by employing high resolution mass spectrometry, 1H NMR and density functional theory calculations as well as checking the solvent viscosity dependent fluorescence, and thus the nucleophilic addition products, the intramolecular charge transfer character, and the aggregation-induced emission behaviour were clearly elucidated. It is noteworthy that the low cytotoxicity, the intrinsic aggregation-induced emission nature and near-infrared emissions enable the application of the probe in living cell imaging.

  • 3. Chen, X.
    et al.
    Zhu, L.
    Wang, D.
    Zou, Q.
    Li, Xin
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Theoretical Chemistry and Biology.
    Chen, W.
    A unimolecular platform based on diarylethene with multiple stimuli-gated photochromism2019In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 164, p. 91-96Article in journal (Refereed)
    Abstract [en]

    The gated photochromic systems have attracted great interest in scientific researches due to their merits in the opto-electronic fields, whereas the multi-stimuli gating function in a unimolecular platform has rarely been addressed. Herein, a new strategy to realize multi-stimuli gated photochromic function was devised relying on a simple Schiff-based diarylethene derivative. The compound shows no photoswitching properties in solution under irradiation with any wavelength of light. It is noteworthy that mecury(II) ions, water and protons can trigger its photo-reactivity independently with different absorption changes, respectively. Therefore, a molecular logic circuit with four inputs, including mecury(II) ions, water, protons and UV light, was fabricated on the basis of the unimolecular platform, suggesting promise for application in multi-controlled photoswitchings. These results could be valuable for the further development of photoswitchings with multiple stimuli responses.

  • 4. El-Zohry, Ahmed M.
    et al.
    Cong, Jiayan
    KTH.
    Karlsson, Martin
    Kloo, Lars
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Zietz, Burkhard
    Ferrocene as a rapid charge regenerator in dye-sensitized solar cells2016In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 132, p. 360-368Article in journal (Refereed)
    Abstract [en]

    Using the reductive power of the ferrocene moiety (Fc), an ultrafast regeneration step via a covalent attachment of a Fc moiety to an organic triphenylamine-based dye (L1) when adsorbed on TiO2 is highlighted. Two modified dyes with one and two Fc moieties attached (L1Fc, and L1Fc2), respectively, were synthesized by addition to the L1 dye. These dyes have been studied spectroscopically using ultrafast transient absorption spectroscopy in the visible and the infrared (IR) regions. In acetonitrile, the results show an ultrafast excited state quenching of the modified dyes due to an expected electron transfer process from the Fc(s) to L1. Adsorbed onto TiO2, an electron transfer process is also detected from Fc to the oxidized dye (L1(+)). Despite the occurrence of an ultrafast regeneration step, the solar cell performance does not improve by the attachment of Fc(s) to the dye L1. Transient absorption measurements in the IR region revealed a fast electron recombination process to the Fc(+) moiety on an average time scale of ca. 300 ps, outcompeting the >12 ns process to L1(+). The reasons for the observed considerably faster recombination rate to Fc(+) than to L1(+) are discussed in detail. This study provides deep spectroscopic insights for such organic dyes utilized to afford ultrafast regeneration step without showing high performance in photovoltaic devices. In addition, this study will improve our understandings for the triangular relationship between the molecular design, electron kinetics, and the performance in photovoltaic devices. (C) 2016 Elsevier Ltd. All rights reserved.

  • 5.
    Grabarz, Anna M.
    et al.
    Wroclaw Univ Technol, Dept Phys & Quantum Chem, Fac Chem, Wyb Wyspianskiego 27, PL-50370 Wroclaw, Poland..
    Jedrzejewska, Beata
    UTP Univ Sci & Technol, Fac Chem Technol & Engn, Seminaryjna 3, PL-85326 Bydgoszcz, Poland..
    Skotnicka, Agnieszka
    UTP Univ Sci & Technol, Fac Chem Technol & Engn, Seminaryjna 3, PL-85326 Bydgoszcz, Poland..
    Natarajan Arul, Murugan
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Theoretical Chemistry and Biology.
    Patalas, Filip
    Nicolaus Copernicus Univ, Fac Chem, Gagarina 7, PL-87100 Torun, Poland..
    Bartkowiak, Wojciech
    Wroclaw Univ Technol, Dept Phys & Quantum Chem, Fac Chem, Wyb Wyspianskiego 27, PL-50370 Wroclaw, Poland..
    Jacquemin, Denis
    Univ Nantes, UMR CNRS 6230, Lab CEISAM, 2 Rue Houssiniere,BP92208, F-44322 Nantes 3, France..
    Osmialowski, Borys
    Nicolaus Copernicus Univ, Fac Chem, Gagarina 7, PL-87100 Torun, Poland..
    The impact of the heteroatom in a five-membered ring on the photophysical properties of difluoroborates2019In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 170, article id 107481Article in journal (Refereed)
    Abstract [en]

    A series of novel BF2 complexes, bearing a five-membered heterocyclic ring (with X = NMe, O, and S), were synthesized and characterized with a focus on the influence of atom exchange on the photophysical properties of both unsubstituted and dimethylamino derivatives. The experimental results show that the optical spectra substantially differ in both sets of dyes. In particular, the dimethylamino series are more strongly affected by heteroatom substitution, i.e., the insertion of X = O or X = S in lieu of X = NMe causes substantial bathochromic shifts of the absorption and emission bands, as well as marked changes in their topologies. In contrast, the optical spectra of the unsubstituted compounds undergo only relatively small red-shifts, and no variation of band shapes is observed. Moreover, the measured absorption spectra of the unsubstituted compounds bearing X = NMe and X = O are almost identical. Interestingly, the fluorescence yields of the dimethylamino derivatives are much larger (up to one order of magnitude) than those of the corresponding unsubstituted compounds. The experimental analyses are supported by state-of-the-art quantum chemistry calculations, which satisfactorily reproduced the experimental trends and provided further insights into the observed optical signatures.

  • 6. Ivaniuk, K.
    et al.
    Cherpak, V.
    Stakhira, P.
    Baryshnikov, Gleb
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology. Bohdan Khmelnytsky National University, Ukraine.
    Minaev, Boris
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology. Bohdan Khmelnytsky National University, Ukraine.
    Hotra, Z.
    Turyk, P.
    Zhydachevskii, Y.
    Volyniuk, D.
    Aksimentyeva, O.
    Penyukh, B.
    Lazauskas, A.
    Tamulevičius, S.
    Grazulevicius, J. V.
    Ågren, Hans
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology. Siberian Federal University, Russian Federation.
    BaZrO3 perovskite nanoparticles as emissive material for organic/inorganic hybrid light-emitting diodes2017In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 145, p. 399-403Article in journal (Refereed)
    Abstract [en]

    In the present work we have demonstrated double-channel emission from organic exciplexes coupled to inorganic nanoparticles. The process is demonstrated by yellow-green emission in light-emitting diodes based on organic exciplexes hybridized with perovskite-type dispersed BaZrO3 nanoparticles. Such double-channel emission provides a broadening of the electroluminescence spectrum and a resultant yellow-green emission color of the device. We have realized an energy transfer from the exciplexes arranged by the interface between two organic layers and the spherical-shaped BaZrO3 nanoparticles randomly deposited on the organic interface constructed of the tris(4-carbazoyl-9-ylphenyl)amine and 4,7-diphenyl-1,10-phenanthroline molecules. The fabricated device exhibits a current efficiency value of 3.88 C d/A, maximum brightness of 3465 cd/m2 (at 15 V), and external quantum efficiency of about 1.26%. In order to estimate the efficiency of the energy transfer from the exciplex to the BaZrO3 nanoparticles we have applied the Förster model for the dipole-dipole energy transfer accounting for the mutual overlap of the exciplex emission spectrum and the absorption spectrum of the BaZrO3 nanoparticles.

  • 7. Ivaniuk, K.
    et al.
    Pidluzhna, A.
    Stakhira, P.
    Baryshnikov, Gleb V.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Theoretical Chemistry and Biology.
    Kovtun, Y. P.
    Hotra, Z.
    Minaev, B. F.
    Ågren, Hans
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Theoretical Chemistry and Biology.
    BODIPY-core 1,7-diphenyl-substituted derivatives for photovoltaics and OLED applications2020In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 175, article id 108123Article in journal (Refereed)
    Abstract [en]

    In the current study we demonstrate an application of four previously synthesized 1,7-diphenyl-substituted BODIPY species for inverted photovoltaic cells and for organic light-emitting devices (OLEDs). Depending on the type of substituents or annulation of the pyridone rings these dyes exhibit spectral properties in the full visible region up to the near-infrared wavelengths. All the studied compounds show very strong visible absorption that can be ascribed to the low lying LUMO levels making them electronically suitable as acceptors for many donor materials. The best fabricated inverted photovoltaic device based on the BODYPI-core derivatives demonstrates a power conversion efficiency equal to 1.36% which is close to previously published reports for related species. Two kinds of deep red OLEDs (doped and undoped) with narrow electroluminescence spectra (full width at half maximum up to 45 nm) have been fabricated. Maximum brightness of 3900 cd m−2 and an external quantum efficiency by 2.3% were achieved for the best OLED structure.

  • 8. Jiang, Tao
    et al.
    Li, Dongyu
    Hang, Yandi
    Gao, Yuting
    Zhang, Hequn
    Zhao, Xinyuan
    Li, Xin
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Li, Bo
    Qian, Jun
    Hua, Jianli
    Tetraphenylethene end-capped diketopyrrolopyrrole fluorogens with AIE and large two-photon absorption cross-sections features and application in bioimaging2016In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 133, p. 201-213Article in journal (Refereed)
    Abstract [en]

    In this work, a series of new diketopyrrolopyrrole-based dyes have been synthesized by connecting tetraphenylethene to the diketopyrrolopyrrole core. All the four compounds exhibit good aggregation induced emission property with nonemissive in the solution but strong red fluorescence in the aggregate or solid state. Also, these new dyes exhibit large two-photon absorption cross sections (a), in which the a data measured by the open aperture Z-scan technique are determined to be 150, 300, 1140 and 1016 GM for four dyes, respectively. In addition, compound with stilbene and four tetraphenylethene units (DPP-TPE-3) was used as the luminogen and encapsulated into nanoparticles for cell imaging and two-photon excited fluorescence blood vessels imaging. The result indicates that it can be used as the effective fluorescence probe for bioimaging and has great potential for bioapplications. (C) 2016 Elsevier Ltd. All rights reserved.

  • 9. Kong, Jiahui
    et al.
    Li, Qizhao
    Li, Minzhi
    Li, Xin
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Liang, Xu
    Zhu, Weihua
    Ågren, Hans
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Xie, Yongshu
    Modulation of the structures and properties of bidipyrrin zinc complexes by introducing terminal alpha-methoxy groups2017In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 137, p. 430-436Article in journal (Refereed)
    Abstract [en]

    A bidipyrrin nickel complex was synthesized in a high yield by oxidatively coupling between the ligands in the corresponding 2:1 (L:M) type of dipyrrin nickel complex, and further demetallation afforded the free bidipyrrin ligand. Interestingly, when treating the bidipyrrin nickel complex or the free bidipyrrin with FeCl3 in CH2Cl2/MeOH, the symmetric di-alpha-methoxy bidipyrrin could be synthesized in a high yield, with two methoxy groups attached to the terminal pyrrolic alpha-positions. Moreover, the coordination of the unsubstituted and disubstituted bidipyrrins with Zn(OAc)(2),2H(2)O afforded two similar M2L2 type of bidipyrrin helical complexes with different ligand conformations and different Zn center dot center dot center dot Zn distances of 5.353 and 3.357 angstrom, respectively. The difference in the conformations may be related to the electrostatic repulsions between the methoxy substituents. These results indicate that the dyes based on helical bidipyrrin zinc complexes with tunable structures and photophysical properties may be developed simply by modulating the terminal alpha-substituents.

  • 10.
    Ledwon, Przemyslaw
    et al.
    Silesian Tech Univ, Fac Chem, PL-44100 Gliwice, Poland..
    Motyka, Radoslaw
    Silesian Tech Univ, Fac Chem, PL-44100 Gliwice, Poland..
    Ivaniuk, Khrystyna
    Lviv Polytech Natl Univ, S Bandera 12, UA-79013 Lvov, Ukraine..
    Pidluzhna, Anna
    Lviv Polytech Natl Univ, S Bandera 12, UA-79013 Lvov, Ukraine..
    Martyniuk, Natalia
    Lviv Polytech Natl Univ, S Bandera 12, UA-79013 Lvov, Ukraine..
    Stakhira, Pavlo
    Lviv Polytech Natl Univ, S Bandera 12, UA-79013 Lvov, Ukraine..
    Baryshnikov, Gleb V.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Theoretical Chemistry and Biology.
    Minaev, Boris F.
    Bohdan Khmelnytsky Natl Univ, Dept Chem & Nanomat Sci, UA-18031 Cherkassy, Ukraine..
    Ågren, Hans
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Theoretical Chemistry and Biology.
    The effect of molecular structure on the properties of quinoxaline-based molecules for OLED applications2020In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 173, article id 108008Article in journal (Refereed)
    Abstract [en]

    Different donor-acceptor-donor (D-A-D) and donor-pi-bridge-acceptor-pi-bridge-donor (D-pi-A-pi-D) systems based on a quinoxaline acceptor are compared. A significant difference in electrochemical and photophysical properties was found depending on molecular structure. A luminescence shift from 539 rim up to 671 nm was observed upon extension of conjugation length. The studied compounds were tested in fluorescent organic light emitting diodes (OLEDs) demonstrating an external quantum efficiency up to 4.5% for a deep red non-doped device and 7% when doped into an exciplex host device. A quantum-chemical interpretation of the electroluminescence spectra for the fabricated OLEDs was carried out including modelling of excimers and exciplexes.

  • 11. Li, Jiajia
    et al.
    Yang, Xichuan
    Cheng, Ming
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Wang, Mei
    Sun, Licheng
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. Dalian Univ Technol, State Key Lab Fine Chem, DUT KTH Joint Educ & Res Ctr Mol Devices, Peoples R China.
    Phenoxazine-based panchromatic organic sensitizers for dye-sensitized solar cells2015In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 116, p. 58-64Article in journal (Refereed)
    Abstract [en]

    A series of metal-free organic dyes LJJ101-LJJ103 composed of phenoxazine unit and indolinum carboxyl acid derivative have been synthesized for dye-sensitized solar cells. A systematic investigation has been conducted for the photology and electrochemistry properties of dyes LJJ101-LJJ103. Panchromatic spectra responses for all the three dyes have been obtained and extended to about 800 nm in near-infrared region. Compared to LJJ101, the introduction of thiophene and squaraine unit causes a red-shift absorption response for LJJ102 and LJJ103, respectively. When applied in dye-sensitized solar cells under AM 1.5 illumination, the device sensitized by LJJ103 yields the best conversion efficiency of 5.1% with a short-circuit photocurrent density of 13.7 mA/cm(2), an open-circuit photovoltage of 502 mV and a fill factor of 74.0%.

  • 12.
    Li, Xin
    et al.
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Li, Wenlong
    E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China.;E China Univ Sci & Technol, Inst Fine Chem, Shanghai Key Lab Funct Mat Chem, Shanghai 200237, Peoples R China..
    Ågren, Hans
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Tian, He
    E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China.;E China Univ Sci & Technol, Inst Fine Chem, Shanghai Key Lab Funct Mat Chem, Shanghai 200237, Peoples R China..
    Zhu, Weihong
    E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China.;E China Univ Sci & Technol, Inst Fine Chem, Shanghai Key Lab Funct Mat Chem, Shanghai 200237, Peoples R China..
    Theoretical insight into the enhanced hindrance, thermal stability and optical properties of diarylethene with a benzobis(thiadiazole) bridge and benzothiophene rings2016In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 125, p. 348-355Article in journal (Refereed)
    Abstract [en]

    To rationalize the effects of intramolecular steric hindrance on the performance of diarylethene photoswitches, we here present a density functional theory study on the thermal bistability and optical properties of a photochromic diarylethene BBTE consisting of a benzobis(thiadiazole) bridge and benzothiophene rings, in which prominent steric hindrance exists owing to the extended structures of is-conjugated groups. Our calculations not only provide rational explanations for the isolation of enantiopure anti-parallel conformers of the open-ring isomer, but also elucidate the detailed pathway of a two-step ground-state ring-opening process, where the thermal stability of the closed-ring isomer is guaranteed by an overall free energy barrier of around 113 kJ mol(-1) (27 kcal mol(-1)). In addition, the tunable intramolecular charge transfer of the donor acceptor structure formed by the benzobis(thiadiazole) bridge and the bulky benzothiophene rings is also addressed within time-dependent density functional theory. Charge transfer excitations in the open- and the closed-ring isomers are characterized as long-range and medium-range, respectively. We show that the diarylethene derivative under investigation can serve as a promising platform for future development of optoelectronic materials.

  • 13. Ma, Xuemei
    et al.
    Wu, Wenjun
    Zhang, Qiong
    KTH, School of Biotechnology (BIO), Theoretical Chemistry.
    Guo, Fuling
    Meng, Fanshun
    Hua, Jianli
    Novel fluoranthene dyes for efficient dye-sensitized solar cells2009In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 82, no 3, p. 353-359Article in journal (Refereed)
    Abstract [en]

    Three, novel, fluoranthene-based dyes, 2-cyano-3-(5-(7,12-diphenylbenzo[k]fluoranthen-3-yl)thiophen-2-yl)acryli c acid, 2-(5-((5-(7,12-diphenylben-zo[k]fluoranthen-3-yl)thiophen-2-yl)methylene )-4-oxo-2-thioxothiazolidin-3-yl)acetic acid and 2-cyano-3-(4-(2-(7,12-diphenylbenzo[k]fluoranthen-3-yl)ethynyl)phenyl) acrylic acid, were synthesized for application as sensitizers in dye-sensitized solar cells. In each dye, the 7,12-diphenyl-benzo[k]fluoranthene moiety acted as electron donor with phenyl and thiophene units as electron spacers and carboxylic acid as electron acceptor. Tuning of the HOMO and LUMO energy levels was conveniently accomplished by changing the spacer and acceptor moiety, as confirmed using electrochemical measurements. Maximum solar energy:electricity conversion efficiency was 4.4% under AM 1.5 solar simulator (100 mW cm(-2)) for 2-cyano-3-(5-(7,12-diphenylbenzo[k]fluoranthen-3-yl)thiophen-2-yl)acryli c acid. The results suggest that dyes based on fluoranthene donor are promising candidates for high performance, dye-sensitized solar cells.

  • 14.
    Minaev, Boris F.
    et al.
    KTH, School of Biotechnology (BIO).
    Baryshnikov, Gleb V.
    Minaeva, Valentina A.
    Electronic structure and spectral properties of the triarylamine-dithienosilole dyes for efficient organic solar cells2012In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 92, no 1, p. 531-536Article in journal (Refereed)
    Abstract [en]

    The recently synthesized high-performance triarylamine dyes with the dithienosilole pi-conjugated spacer for efficient organic solar cells are calculated at the density functional theory (DFT) level with the Bader approach for the quantum theory of atoms in molecule (QTAIM) analysis. The presence of stabilizing intramolecular hydrogen bonds and Van der Waals interactions in the dye molecules is predicted and the energies of these interactions are estimated. The electronic bands nature in absorption spectra of the dyes is determined by the time-dependent DFT calculations with a linear response methodology using B3LYP and BMK hybrid functionals. Relations between incident light absorption intensity in the first long-wavelength band of the dye, its polarization, HOMO-LUMO orbital nature and the driving force of electron injection to the semiconductor are discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  • 15.
    Pidluzhna, A.
    et al.
    Lviv Polytech Natl Univ, Stepan Bandera 12, UA-79013 Lvov, Ukraine..
    Ivaniuk, K.
    Lviv Polytech Natl Univ, Stepan Bandera 12, UA-79013 Lvov, Ukraine..
    Stakhira, P.
    Lviv Polytech Natl Univ, Stepan Bandera 12, UA-79013 Lvov, Ukraine..
    Hotra, Z.
    Lviv Polytech Natl Univ, Stepan Bandera 12, UA-79013 Lvov, Ukraine.;Rzeszow Univ Technol, Al Powstancow Warszawy 12, PL-35959 Rzeszow, Poland..
    Chapran, M.
    Lodz Univ Technol, Dept Mol Phys, Zeromskiego 116, PL-90924 Lodz, Poland..
    Ulanski, J.
    Lodz Univ Technol, Dept Mol Phys, Zeromskiego 116, PL-90924 Lodz, Poland..
    Tynkevych, O.
    Yuriy Fedkovych Chernivtsi Natl Univ, Kotsiubynsky Str 2, UA-58012 Chernovtsy, Ukraine..
    Khalavka, Y.
    Yuriy Fedkovych Chernivtsi Natl Univ, Kotsiubynsky Str 2, UA-58012 Chernovtsy, Ukraine..
    Baryshnikov, Gleb V.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Theoretical Chemistry and Biology.
    Minaev, B. F.
    Bohdan Kitmelnytsky Natl Univ, Dept Chem & Nanomat Sci, UA-18031 Cherkassy, Ukraine..
    Ågren, Hans
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Theoretical Chemistry and Biology.
    Multi-channel electroluminescence of CdTe/CdS core-shell quantum dots implemented into a QLED device2019In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 162, p. 647-653Article in journal (Refereed)
    Abstract [en]

    CdTe/CdS core-shell quantum dots were synthesized and implemented into a light emitting device resulting in multi-channel electroluminescence with a light-green emission color. The main electroluminescence band at about 530 nm corresponds to the emission by the CdTe core (type I core/shell structure), while the next emission band at 595 nm is assigned to the crossed recombination of electrons from the conduction band of the CdS shell and holes from the valence band of the CdTe core (type II core/shell structure). At the same time, the photoluminescence spectrum of the synthesized CdTe/CdS core-shell quantum dots contains only one emission band distinctive for type II structures. This behavior of CdTe/CdS core-shell quantum dots upon the electroexcitation allows the extension of the electroluminescence spectrum in the optical region in a way that is useful for lighting source applications. Such multi-channel electroluminescence can most probably also be reproduced in related core-shell systems accounting for size-confinement between the core size and shell thickness.

  • 16. Song, Heli
    et al.
    Li, Xin
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Ågren, Hans
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Xie, Yongshu
    Branched and linear alkoxy chains-wrapped push-pull porphyrins for developing efficient dye-sensitized solar cells2017In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 137, p. 421-429Article in journal (Refereed)
    Abstract [en]

    Four alkoxy-wrapped push-pull porphyrin dyes containing the phenothiazine derived donor and the ethynylbenzoic acid acceptor have been designed, synthesized and used as sensitizers for fabricating efficient dye-sensitized solar cells (DSSCs). Branched or linear alkoxy chains were introduced to the ortho-positions of the meso-phenyl moieties to suppress the dye aggregation and charge recombination. The effect of alkoxy chains were investigated in the absence and presence of an additional electron withdrawing benzothiadiazole unit. In the former cases, almost identical photovoltaic efficiencies of similar to 8.3% were achieved for both the branched and the linear alkoxy chains, while in the latter cases, the planar benzothiadiazole unit induces serious dye aggregation and charge recombination, resulting in lower efficiencies of 6.46% and 7.50% for the linear and branched chains, respectively, even though broader absorption was achieved. The relatively higher efficiency achieved for the dyes with branched chains may be related to the better effect of suppressing the dye aggregation and charge recombination. Furthermore, the coadsorption approach was employed, and a highest efficiency of 9.62% was achieved for the dye that features branched chains and the benzothiadiazole unit. These results compose a novel approach for developing efficient DSSCs by combining the coadsorbent with a porphyrin dye containing both the additional benzothiadiazole acceptor and branched alkoxy chains.

  • 17.
    Tang, Yunyu
    et al.
    Chinese Acad Fishery Sci, Lab Qual Safety & Proc Aquat Prod, East China Sea Fisheries Res Inst, Jungong 300, Shanghai 200090, Peoples R China..
    Wang, Yueqiang
    East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Meilong 130, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Meilong 130, Shanghai 200237, Peoples R China..
    Song, Heli
    East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Meilong 130, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Meilong 130, Shanghai 200237, Peoples R China..
    Liu, Qingyun
    Shandong Univ Sci & Technol, Coll Chem & Environm Engn, Qingdao, Shandong, Peoples R China..
    Li, Xin
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Theoretical Chemistry and Biology.
    Cai, Youqiong
    Chinese Acad Fishery Sci, Lab Qual Safety & Proc Aquat Prod, East China Sea Fisheries Res Inst, Jungong 300, Shanghai 200090, Peoples R China..
    Xie, Yongshu
    East China Univ Sci & Technol, Sch Chem & Mol Engn, Key Lab Adv Mat, Meilong 130, Shanghai 200237, Peoples R China.;East China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, Meilong 130, Shanghai 200237, Peoples R China..
    Solar cells sensitized with porphyrin dyes with a carbazole donor: The effects of an auxiliary benzothiadiazole acceptor and bulky substituents on the donor2019In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 171, article id UNSP 107776Article in journal (Refereed)
    Abstract [en]

    Three porphyrin sensitizers XW54-XW56 containing a carbazole donor have been designed and synthesized by introducing a benzothiadiazole (BTD) unit as the auxiliary electron acceptor to extend the absorption spectra and/or bulky dihexyloxyphenyl groups into the carbazole unit to suppress dye aggregation and improve the photovoltage (V-OC). The BTD unit incorporated in XW54 obviously broadens and red-shifts the absorption threshold to ca. 700 nm, as compared with that of 650 nm observed for XW1. Thus, XW54 exhibits a much broader monochromatic photon-to-electron conversion efficiency (IPCE) spectrum with an extremely red-shifted onset wavelength of 780 nm, resulting in a photocurrent density (J(SC)) of 11.60 mA cm(-2), higher than that of XW1. Unfortunately, the V-OC value was decreased owing to the more severe dye aggregation caused by the large conjugation framework induced by the presence of the BTD unit. As a result, XW54 shows an efficiency of 6.26%, slightly higher than that of 6.11% obtained for XW1. On the other hand, with the bulky dihexyloxyphenyl donor groups introduced to XW55, a highest V-OC, of 860 mV was achieved, which can be ascribed to the efficient prevention of charge recombination and suppression of dye aggregation. Thus, XW55-based cells exhibit an improved efficiency of 6.60%. On the basis of XW54 and XW55, two bulky dihexyloxyphenyl groups and a BTD unit were simultaneously introduced to XW56, affording a highest efficiency of 7.03%, with the J(SC )and V-OC, values of 12.5 mA cm(-2) and 785 mV, respectively. These results compose a novel approach for developing efficient dye-sensitized solar cells (DSSCs) by simultaneously introducing bulky dihexyloxyphenyl groups and a benzothiadiazole unit, which may synergistically broaden the absorption spectra and suppress the dye aggregation, resulting in improved photocurrent and photovoltage.

  • 18. Tian, Haining
    et al.
    Yang, Xichuan
    Cong, Jiayan
    Chen, Ruikui
    Teng, Chao
    Liu, Jing
    Hao, Yan
    Wang, Lei
    Sun, Licheng
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. KTH, School of Chemical Science and Engineering (CHE), Centres, Centre of Molecular Devices, CMD.
    Effect of different electron donating groups on the performance of dye-sensitized solar cells2010In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 84, no 1, p. 62-68Article in journal (Refereed)
    Abstract [en]

    A series of organic sensitizers containing identical pi-spacers and electron acceptors but different, aromatic amine electron-donating groups, were used in dye-sensitized solar cells to study the effect of the electron donating groups on device performance. The derived photophysical and photovoltaic properties, as well as density functional theory calculations, revealed that the tetrahydroquinoline dye was prone to aggregate upon the surface of titanium dioxide owing to the dye's planar structure. A 45% improvement in efficiency of a tetrahydroquinoline dye based cell was achieved when chenodeoxycholic acid was employed as co-adsorbent. However, the airscrew type of triphenylamine unit and Y type structure of the substituted phenothiazine framework suppressed dye aggregation on titanium dioxide. The efficiency of a phenothiazine dye-based cell fabricated using saturated co-adsorbent in dichloromethane was only 15% greater than that achieved in the absence of co-adsorbent. Electrochemical Impedance Spectroscopy was used to determine the interfacial charge transfer process occurring in solar cells that employed different dyes in both the absence and presence of chenodeoxycholic acid as co-adsorbent.

  • 19.
    Wang, Jia-Xing
    et al.
    Dongguan Univ Technol, 1 Daxue Rd, Dongguan 523808, Peoples R China..
    Li, Xin
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Theoretical Chemistry and Biology.
    Li, Chen
    Dongguan Univ Technol, 1 Daxue Rd, Dongguan 523808, Peoples R China..
    Constructing photochromic diarylethene with NIR-absorption beyond 800 nm2021In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 189, article id 109273Article in journal (Refereed)
    Abstract [en]

    Near-infrared (NIR) absorbing dyes have received increasing attention due to their ability of NIR radiation absorption and efficient light-to-heat conversion. NIR absorbing photochromic diarylethene (DAE) materials, which could modulate NIR absorption upon light stimulation, provide a convenient route to fabricate smart NIR absorbers. In this study, we constructed a new NIR absorbing photochromic DAE system, of which NIR absorption stems from closed isomer bearing triarylamine (TAA) radical (TDEc-ox). Upon 365/440 nm light irradiation, the open isomer TDEo undergoes photo-oxidation and cyclization to yield TDEc-ox, which exhibited NIR absorption at 928 nm in chloroform. TDEc-ox possesses a photo-inactive feature facilitating non-destructive readout of NIR absorption and high stability (lifetime time ? 3 days). Contrary to TDEo, the closed isomer TDEc cannot be directly photo-oxidized to give TDEc-ox. This discrepancy makes TDEc a ?photogenerated TAA radical reservoir?: after cycles of photoisomerization, a controllable accumulation of NIR absorbing TDEc-ox can be achieved.

  • 20. Wang, Lei
    et al.
    Yang, Xichuan
    Wang, Xiuna
    Sun, Licheng
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Novel organic dyes with anchoring group of quinoxaline-2, 3-diol and the application in dye-sensitized solar cells2015In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 113, p. 581-587Article in journal (Refereed)
    Abstract [en]

    Two organic quinoxaline dyes (WQ-1 and WQ-2) with a structure of quinoxaline-2, 3-diol as the electron withdrawing and anchoring group were synthesized and applied in the dye-sensitized solar cells. Fourier transform infrared spectroscopy and two other reference dyes (WQ-R1 and WQ-R2) without the hydroxyl groups were introduced to ascertain the adsorption properties of the dye series. The effect of the new electron acceptor and anchoring group on the performance of solar cells was investigated systematically. Under the standard light illumination (100 mW m(-2)), WQ-2 got an efficiency of 2.25%, with a short circuit photocurrent density of 5.51 mA cm(-2), an open circuit voltage of 0.612 V and a fill factor of 66.74%.

  • 21. Wei, X.
    et al.
    Bu, L.
    Li, Xin
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Ågren, Hans
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Xie, Y.
    Full color emissions based on intramolecular charge transfer effect modulated by formyl and boron-dipyrromethene moieties2017In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 136, p. 480-487Article in journal (Refereed)
    Abstract [en]

    From the simple one-pot Vilsmeier formylation of 9-diphenylaminoanthracence, mono-, di- and tri-formyl products were successfully synthesized and the yields for the individual products can be optimized by varying the equivalents of the Vilsmeier reagent and changing the reaction temperature. The four obtained aldehydes exhibit distinct optical properties, with the emission maxima varying in a large wavelength range of 455–593 nm, despite their similar structures. The intramolecular charge transfer effect can be effectively modulated by varying the numbers and positions of the formyl groups, resulting in the observed distinct optical properties. Based on the aldehydes, the corresponding boron-dipyrromethenes were also synthesized. Similarly, the intramolecular charge transfer effect and the optical properties can be effectively modulated by the numbers and positions of the boron-dipyrromethene moieties. To further modulate the intramolecular charge transfer effect and red shift the emission, the dimethoxy-substituted 9-diphenylaminoanthracence was also used for synthesizing the corresponding aldehyde and boron-dipyrromethene. Thus, full color emissions within the wavelength range of 455–704 nm were successfully achieved based on modulating the intramolecular charge transfer.

  • 22. Yang, X. C.
    et al.
    Wu, Z. W.
    Sun, Licheng C.
    Ni, C. J.
    The bromination mechanism of 1-aminoanthraquinone-2,4-disulfonic acid in sulfuric acid2006In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 71, no 3, p. 231-235Article in journal (Refereed)
    Abstract [en]

    I-Amino-4-bromoanthraquinotie-2-sulfoiiic acid (bromoamine acid) is an important intermediate for dyes. 1-Aminoanthraquinone2,4-disulfonic acid is the major impurity when 1-aminoanthraquinone is sulfonated in oleum to synthesize bromoamine acid. The mechanism of bromination of 1-aminoanthraquinone-2,4-disulfonic acid in sulfuric acid has been studied. It is proved that I-aminoanthraquinone-2,4-disulfonic acid undergoes de-sulfonation first to form 1-aminoanthraquinoine-2-sulfonic acid, and then bromination to form bromoamine acid. Based on this mechanism, a new optimal process for the synthesis of bromoamine acid is developed. In this way, bromoamine acid is afforded in high yield and good quality.

  • 23. Zakrzewska, A.
    et al.
    Zaleśny, R.
    Kolehmainen, E.
    Ośmiałowski, B.
    Jȩdrzejewska, B.
    Ågren, Hans
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Pietrzak, M.
    Substituent effects on the photophysical properties of fluorescent 2-benzoylmethylenequinoline difluoroboranes: A combined experimental and quantum chemical study Dedication: This publication is dedicated to the memory of Prof. Jerzy Pa̧czkowski.2013In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 99, no 3, p. 957-965Article in journal (Refereed)
    Abstract [en]

    In this study, we demonstrate a successful synergy between theory and experiment and report on the photophysical properties of a recently synthesized series of substituted 2-benzoylmethylenequinoline difluoroboranes with a view towards the effect of substitution on their properties. In general difluoroboranes are known to have a bright fluorescence but for some analogs the properties are not fully understood. Quantum chemistry methods have been applied in order to explain a complex structure of the absorption and emission spectra and to gain an insight into the charge redistribution upon the excitation of the investigated molecules. We demonstrate that the spectra of this important class of compounds can be satisfactorily simulated using quantum chemistry methods. In particular, the absorption and emission band structure was resolved and the spectral features were assigned to C-H wagging and skeletal vibrations of the polycyclic core.

  • 24.
    Zhang, Qiong
    et al.
    KTH, School of Biotechnology (BIO), Theoretical Chemistry.
    Ning, Zhijun
    Tian, He
    'Click' synthesis of starburst triphenylamine as potential emitting material2009In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 81, no 1, p. 80-84Article in journal (Refereed)
    Abstract [en]

    The efficient synthesis of a starburst triphenylamine, tris(4-(1-(4-(diphenylamino)phenyl)-1H-1,2,3-triazol-4-yl)phenyl)amine, via straightforward 'click coupling' of 4-azido-N,N-diphenylbenzenamine and tris(4-ethynylphenyl)amine is reported. The reaction was performed in THF using (PPh3)(3)CuBr as catalyst and was accomplished within 6 h in high yield (92%). Both the synthesis and purification steps were greatly simplified in comparison with conventional methods. The optical, electrochemical, and thermal properties of the starburst triphenylamine were examined: the synthesized compound emitted deep blue fluorescence in both solution and the solid state and displayed reversible redox processes. The starburst triphenylamine is a potential hole-transporting material and blue-light-emitting material.

  • 25.
    Zhu, Ning
    et al.
    E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China.;E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China..
    Li, Xin
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Wang, Yuan
    Chinese Acad Sci, Key Lab Photochem Convers & Optoelect Mat, Tech Inst Phys & Chem, Beijing 100190, Peoples R China..
    Ma, Xiang
    E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China.;E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China..
    Photo-responsive chiral cyclic molecular switches based on stiff stilbene2016In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 125, p. 259-265Article in journal (Refereed)
    Abstract [en]

    Two novel photo-responsive chiral cyclic molecular switches constituted of stiff stilbene and binaphthyl moieties connected through alkyl chains of different length were fabricated. The cyclization synthetic strategy employed herein made it convenient to obtain the pure Z isomers rather than Z/E isomer mixtures. The detailed photo-switching behaviors of target compounds were studied by the UV-Vis absorption and circular dichroism spectra in dichloromethane. The twist angles of the binaphthyl of the switches were able to be reversibly modulated by Z/E isomerization of stiff stilbene unit under alternative UV light stimuli and influenced by the length of alkyl chain to some extent.

  • 26. Zou, Qi
    et al.
    Li, Xin
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Zhou, Ji
    Bai, Kangkang
    Ågren, Hans
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Synthesis and photochromism of a spirooxazine derivative featuring a carbazole moiety: Fast thermal bleaching and excellent fatigue resistance2014In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 107, p. 174-181Article in journal (Refereed)
    Abstract [en]

    A novel photochromic spirooxazine derivative bearing a carbazole moiety (SOC) was synthesized and studied in solution under flash photolysis conditions. It is found to exhibit excellent characteristics like high photochromic response, large steady-state optical density, fast thermal bleaching rate and good fatigue-resistance. The effect of different solvents on the photochromic properties of the compound was evaluated, revealing that the photochromic properties can be modulated by different solvents based on the corresponding polarity. The mechanism and kinetics of the thermal fading process of compound SOC were additionally investigated by theoretical simulations, where the isomerization pathway from the trans-trans-cis conformation was found to be several times faster than that from the cis-trans-cis conformation. This type of fast-bleaching and fatigue-resistent photochromic compounds is expected to pave an exciting avenue in future development of high-performance photochromic materials.

  • 27. Zou, Qi
    et al.
    Li, Xin
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Ågren, Hans
    KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.
    Configurable photochromism of an unsymmetrical dithienylethene derivative by Cu2+ ions or water2014In: Dyes and pigments, ISSN 0143-7208, E-ISSN 1873-3743, Vol. 111, p. 1-7Article in journal (Refereed)
    Abstract [en]

    We describe a gated photochromic behavior of an unsymmetrical dithienylethene derivative, which is intrinsically inert to photoisomerization in organic solvents and which is activated by addition of Cu2+ ions or water. The mechanism behind the gated photochromic property is interpreted by theoretical simulations, suggesting that the energy levels of frontier molecular orbitals are altered by the interaction of the Schiff base moiety with Cu2+ ions or water molecules. Potential applications of such gated photochromic materials have been exemplified not only by the reversible interchange between the photoactive and photoinactive states triggered by Cu2+ ions and EDTA, but also by the construction of a keypad with sequence-dependent input signals at the molecular level.

1 - 27 of 27
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