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  • 1.
    REN, Yansong
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Kravchenko, Oleksandr
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Xie, Sheng
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Grape, Erik
    Inge, A. Ken
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Stimuli-responsive Enaminitrile Molecular Switches as Tunable AIEgens Covering theChromaticity Space and Acting as Vapor SensorsManuscript (preprint) (Other academic)
    Abstract [en]

    A family of responsive enaminitrile molecular switches showing tunable turn-onfluorescence upon switching and aggregation is reported. Activated by addition of acid/base,isomerization around the C=C bond could be effectuated, resulting in complete, reversible switchingto the E- or Z-isomers. Typical aggregation-induced emission could be recorded for one specificstate of the different switches. By subtle tailoring of the parent structure, a series of compounds withemission covering almost the full visible color range were obtained. The switchable AIE features ofthe enaminitrile structures enabled their demonstration as solid state chemosensors to detect acidicand basic vapors, where the emission displayed an “off-on-off” effect. X-ray crystal analysis andDFT calculations suggested a restriction of intramolecular rotation mechanism, and anintramolecular charge transfer effect in the AIE luminogens.

  • 2.
    Ren, Yansong
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. KTH - Royal Institute of Technology.
    Xie, Sheng
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Grape, Erik
    Inge, A. Ken
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Multistimuli-Responsive Enaminitrile Molecular Switches DisplayingH+‑Induced Aggregate Emission, Metal Ion-Induced Turn-OnFluorescence, and Organogelation Properties2018In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 140, no 42, p. 13640-13643Article in journal (Refereed)
    Abstract [en]

    Multistimuli-responsive enaminitrile-based configurational switches displaying aggregation-induced emission (AIE), fluorescence turn-on effects, and supergelation properties are presented. The E-isomers dominated (>97%) in neutral/basic solution, and the structures underwent precisely controlled switching around the enamine C═C bond upon addition of acid/base. Specific fluorescence output was observed in response to different external input in the solution and solid states. In response to H+, configurational switching resulted in complete formation of the nonemissive Z-H+-isomers in solution, however displaying deep-blue to blue fluorescence (ΦF up to 0.41) in the solid state. In response to CuII in the solution state, the E-isomers exhibited intense, turn-on, blue-green fluorescence, which could be turned off by addition of competitive coordination. The acid/base-activated switching, together with the induced AIE-effects, further enabled the accomplishment of a responsive superorganogelator. In nonpolar solvents, a blue-fluorescent supramolecular gel was formed upon addition of acid to the E-isomer suspension. The gelation could be reversed by addition of base, and the overall, reversible process could be repeated at least five cycles.

  • 3.
    Xie, Sheng
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, China.
    Manuguri, Sesha
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. University of Massachusetts Lowell, 1 University Ave., Lowell, MA 01854, United States.
    Yan, Mingdi
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry. University of Massachusetts Lowell, 1 University Ave., Lowell, MA 01854, United States.
    Impact of Hydrogen Bonding on the Fluorescence of N-Amidinated Fluoroquinolone2019In: Chemistry - An Asian Journal, ISSN 1861-4728, E-ISSN 1861-471X, Vol. 14, no 6, p. 910-916Article in journal (Refereed)
    Abstract [en]

    The fluorescence properties of AIE-active N-amidinated fluoroquinolones, efficiently obtained by a perfluoroaryl azide-aldehyde-amine reaction, have been studied. The fluorophores were discovered to elicit a highly sensitive fluorescence quenching response towards guest molecules with hydrogen-bond-donating ability. This effect was evaluated in a range of protic/aprotic solvents with different H-bonding capabilities, and also in aqueous media. The influence of acid/base was furthermore addressed. The hydrogen-bonding interactions were studied by IR, NMR, UV/Vis and time-resolved fluorescence decay, revealing their roles in quenching of the fluorescence emission. Due to the pronounced quenching property of water, the N-amidinated fluoroquinolones could be utilized as fluorescent probes for quantifying trace amount of water in organic solvents.

  • 4.
    Xie, Sheng
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Zhou, Juan
    Chen, Xuan
    Univ Massachusetts Lowell, Dept Chem, Lowell, MA 01854 USA..
    Kong, Na
    Fan, Yanmiao
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Hammer, Gerry
    Univ Washington, Dept Bioengn, Natl ESCA & Surface Anal Ctr Biomed Problems, Seattle, WA 98195 USA.;Univ Washington, Dept Chem Engn, Natl ESCA & Surface Anal Ctr Biomed Problems, Seattle, WA 98195 USA..
    Castner, David G.
    Univ Washington, Dept Bioengn, Natl ESCA & Surface Anal Ctr Biomed Problems, Seattle, WA 98195 USA.;Univ Washington, Dept Chem Engn, Natl ESCA & Surface Anal Ctr Biomed Problems, Seattle, WA 98195 USA..
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Yan, Mingdi
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    A versatile catalyst-free perfluoroaryl azide-aldehyde-amine conjugation reaction2019In: MATERIALS CHEMISTRY FRONTIERS, ISSN 2052-1537, Vol. 3, no 2, p. 251-256Article in journal (Refereed)
    Abstract [en]

    In a tri-component reaction, an electrophilically-activated perfluoroaryl azide, an enolizable aldehyde and an amine react readily at room temperature without any catalysts in solvents including aqueous conditions to yield a stable amidine conjugate. The versatility of this reaction is demonstrated in the conjugation of an amino acid without prior protection of the carboxyl group, and in the synthesis of antibiotic-nanoparticle conjugates.

  • 5.
    Zhang, Yang
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemical Engineering and Technology, Energy Processes.
    Xie, Sheng
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Yan, Mingdi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ramström, Olof
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Dynamic Covalent Chemistry of Aldehyde Enamines: Bi-III- and Sc-III-Catalysis of Amine-Enamine Exchange2017In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 23, no 49, p. 11908-11912Article in journal (Refereed)
    Abstract [en]

    The dynamic exchange of enamines from secondary amines and enolizable aldehydes has been demonstrated in organic solvents. The enamine exchange with amines was efficiently catalyzed by Bi(OTf)(3) and Sc(OTf)(3) (2mol%) and the equilibria (60mm) could be attained within hours at room temperature. The formed dynamic covalent systems displayed high stabilities in basic environment with <2% by-product formation within one week after complete equilibration. This study expands the scope of dynamic C-N bonds from imine chemistry to enamines, enabling further dynamic methodologies in exploration of this important class of structures in systems chemistry.

  • 6.
    Zhang, Yang
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemical Engineering, Energy Processes.
    Xie, Sheng
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Yan, Mingdi
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Enzyme- and ruthenium-catalyzed dynamic kinetic resolution involving cascade alkoxycarbonylations for asymmetric synthesis of 5-Substituted N-Aryloxazolidinones2019In: Molecular Catalysis, ISSN 2468-8231, Vol. 470, p. 138-144Article in journal (Refereed)
    Abstract [en]

    AAsymmetric synthesis of N-aryloxazolidinones via dynamic kinetic resolution was developed. A ruthenium-based catalyst was used in the racemization of beta-anilino alcohols, while Candida antarctica lipase B (CAL-B) was applied for two selective alkoxycarbonylations operating in cascade. Various N-aryloxazolidinone derivatives were obtained in high yields and good enantiopurities.

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