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  • 1. Baias, Maria
    et al.
    Dumez, Jean-Nicolas
    Svensson, Per Henrik
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Schantz, Staffan
    Day, Graeme M.
    Emsley, Lyndon
    De Novo Determination of the Crystal Structure of a Large Drug Molecule by Crystal Structure Prediction-Based Powder NMR Crystallography2013In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 135, no 46, p. 17501-17507Article in journal (Refereed)
    Abstract [en]

    The crystal structure of form 4 of the drug 4-[4-(2-adamantylcarbamoyl)-5-tert-butyl-pyrazol-1-yl]benzoic acid is determined using a protocol for NMR powder crystallography at natural isotopic abundance combining solid-state H-1 NMR spectroscopy, crystal structure prediction, and density functional theory chemical shift calculations. This is the first example of NMR crystal structure determination for a molecular compound of previously unknown structure, and at 422 g/mol this is the largest compound to which this method has been applied so far.

  • 2. Bergman, J.
    et al.
    Pettersson, B.
    Hasimbegovic, V.
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry. AstraZeneca R&D, Pharmaceut Dev, Sweden.
    Thionations using a P4S10-pyridine complex in solvents such as acetonitrile and dimethyl sulfone2011In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 76, no 6, p. 1546-1553Article in journal (Refereed)
    Abstract [en]

    Tetraphosphorus decasulfide (P 4S 10) in pyridine has been used as a thionating agent for a long period of time. The moisture-sensitive reagent has now been isolated in crystalline form, and the detailed structure has been determined by X-ray crystallography. The thionating power of this storable reagent has been studied and transferred to solvents such as acetonitrile in which it has proven to be synthetically useful and exceptionally selective. Its properties have been compared with the so-called Lawesson reagent (LR). Particularly interesting are the results from thionations at relatively high temperatures (̃165 °C) in dimethyl sulfone as solvent. Under these conditions, for instance, acridone and 3-acetylindole could quickly be transformed to the corresponding thionated derivatives. Glycylglycine similarly gave piperazinedithione. At these temperatures, LR is inefficient due to rapid decomposition. The thionated products are generally cleaner and more easy to obtain because in the crystalline reagent, impurities which invariably are present in the conventional reagents, P 4S 10 in pyridine or LR, have been removed.

  • 3. Bergman, Jan
    et al.
    Arewang, Carl-Johan
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry. SP Process Development, Sweden .
    Oxidative Ring Expansion of Spirocyclic Oxindole Derivatives2014In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 79, no 19, p. 9065-9073Article in journal (Refereed)
    Abstract [en]

    Oxidation of the spirocyclic oxindole derivative, isamic acid 1, led to decarboxylation and ring expansion to quinazolino[4,5-b]quinazoline-6,8-dione 7 rather than, as previously believed, its isomer 6. The structure of 7 was confirmed by X-ray crystallography. Condensation of isatin (indole-2,3-dione) and 2-aminobenzamide led to the spirocyclic molecule, spiro[3H-indole-3,2'(1H)quinazoline]-2,4'(1H,3H)dione 8, which was also identified as an intermediate in the oxidation of isamic acid. Mild hydrolysis of 7 gave the 10-membered molecule 22. Isamic acid could easily be converted to N-nitrosoisamic acid, which when heated in ethanol underwent a ring expansion to a hydroximino derivative, 38, of compound 6. The structure of 38 was confirmed by X-ray crystallography.

  • 4. Brice, Heloise
    et al.
    Gill, Duncan M.
    Goldie, Laura
    Keegan, Philip S.
    Kerr, William J.
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Inorganic Chemistry.
    Stereocontrolled access to optically-enriched oxabispidines2012In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 48, no 40, p. 4836-4838Article in journal (Refereed)
    Abstract [en]

    A range of chiral, optically-enriched bicyclic oxabispidines were prepared from (S)-(-)-2,3-epoxypropylphthalimide using an efficient sequence featuring a stereocontrolled intramolecular Mannich reaction as the key transformation.

  • 5. Briggner, Lars-Erik
    et al.
    Hendrickx, Ramon
    Kloo, Lars
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Inorganic Chemistry.
    Rosdahl, Jan
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Inorganic Chemistry.
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Inorganic Chemistry.
    Solid-State Perturbation for Solubility Improvement: A Proof of Concept2011In: ChemMedChem, ISSN 1860-7179, Vol. 6, no 1, p. 60-62Article in journal (Refereed)
    Abstract [en]

    Simple and rational: The intrinsic solubility of a compound can be systematically improved by perturbing key interactions in its crystal structure. By carefully choosing the perturbation, the end result will be a molecule similar to the original one, but with significantly higher solubility. This methodology is demonstrated on a subset of benzodiazepines, resulting in significant improvement of their solubility.

  • 6. Briggner, Lars-Erik
    et al.
    Kloo, Lars
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Rosdahl, Jan
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    In Silico Solid State Perturbation for Solubility Improvement2014In: ChemMedChem, ISSN 1860-7179, E-ISSN 1860-7187, Vol. 9, no 4, p. 724-726Article in journal (Refereed)
    Abstract [en]

    Solubility is a frequently recurring issue within pharmaceutical industry, and new methods to proactively resolve this are of fundamental importance. Here, a novel methodology is reported for intrinsic solubility improvement, using insilico prediction of crystal structures, by perturbing key interactions in the crystalline solid state. The methodology was evaluated with a set of benzodiazepine molecules, using the two-dimensional molecular structure as the only a priori input. The overall trend in intrinsic solubility was correctly predicted for the entire set of benzodiazepines molecules. The results also indicate that, in drug compound series where the melting point is relatively high (i.e., brick dust compounds), the reported methodology should be very suitable for identifying strategically important molecular substitutions to improve solubility. As such, this approach could be a useful predictive tool for rational compound design in the early stages of drug development.

  • 7.
    Cong, Jiayan
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Kinschel, Dominik
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry. Dyenamo AB, Sweden.
    Daniel, Quentin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Safdari, Majid
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Gabrielsson, E.
    Chen, Hong
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. SP Process Development Forskargatan, Sweden.
    Sun, Licheng
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. Dalian University of Technology (DUT), China.
    Kloo, Lars
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Bis(1,1-bis(2-pyridyl)ethane)copper(i/II) as an efficient redox couple for liquid dye-sensitized solar cells2016In: Journal of Materials Chemistry A, ISSN 2050-7488, Vol. 4, no 38, p. 14550-14554Article in journal (Refereed)
    Abstract [en]

    A new redox couple, [Cu(bpye)2]+/2+, has been synthesized, and applied in dye-sensitized solar cells (DSSCs). Overall efficiencies of 9.0% at 1 sun and 9.9% at 0.5 sun were obtained, which are considerably higher than those obtained for cells containing the reference redox couple, [Co(bpy)3]2+/3+. These results represent a record for copper-based complex redox systems in liquid DSSCs. Fast dye regeneration, sluggish recombination loss processes, faster electron self-exchange reactions and suitable redox potentials are the main reasons for the observed increase in efficiency. In particular, the main disadvantage of cobalt complex-based redox couples, charge-transport problems, appears to be resolved by a change to copper complex redox couples. The results make copper complex-based redox couples very promising for further development of highly efficient DSSCs.

  • 8.
    Gao, Jiajia
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Fischer, Andreas C.
    KTH, School of Electrical Engineering (EES), Micro and Nanosystems.
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Kloo, Lars
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Crystallography as Forensic Tool for Understanding Electrolyte Degradation in Dye-sensitized Solar Cells2017In: CHEMISTRYSELECT, ISSN 2365-6549, Vol. 2, no 4, p. 1675-1680Article in journal (Refereed)
    Abstract [en]

    The precipitation of solid compounds from model electrolytes for liquid dye-sensitized solar cells has a story to tell regarding decomposition processes to be expected in such systems. Of course, the crystal lattice energy for a specific crystalline compounds plays a role in what compound that will eventually precipitate, but the compounds nevertheless serve as indicators for what type of processes that take place in the solar cell electrolytes upon ageing. From the compounds isolated in this study we learn that both ligand exchange processes, double-salt precipitation and oxidation are degradation processes that should not be overlooked when formulating efficient and stable electrolytes for this type of electrochemical system.

  • 9.
    Gao, Jiajia
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Applied Physical Chemistry.
    Yang, Wenxing
    Uppsala Univ, Angstrom Lab, Dept Chem, Box 523, SE-75120 Uppsala, Sweden..
    El-Zohry, Ahmed M.
    Uppsala Univ, Angstrom Lab, Dept Chem, Box 523, SE-75120 Uppsala, Sweden..
    Prajapati, Govind Kumar
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Applied Physical Chemistry.
    Fang, Yuan
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Applied Physical Chemistry.
    Dai, Jing
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Applied Physical Chemistry.
    Hao, Yan
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Applied Physical Chemistry.
    Leandri, Valentina
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Applied Physical Chemistry.
    Svensson, Per H.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Applied Physical Chemistry. RISE Surface Proc Formulat, Forskargatan 20j, SE-15136 Sodertalje, Sweden..
    Furo, Istvan
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Applied Physical Chemistry.
    Boschloo, Gerrit
    Uppsala Univ, Angstrom Lab, Dept Chem, Box 523, SE-75120 Uppsala, Sweden..
    Lund, Torben
    Roskilde Univ, Dept Sci & Environm, DK-4000 Roskilde, Denmark..
    Kloo, Lars
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Applied Physical Chemistry.
    Light-induced electrolyte improvement in cobalt tris(bipyridine)-mediated dye-sensitized solar cells2019In: Journal of Materials Chemistry A, ISSN 2050-7488, Vol. 7, no 33, p. 19495-19505Article in journal (Refereed)
    Abstract [en]

    Lithium-ion-free tris(2,2 '-bipyridine) Co(ii/iii)-mediated electrolytes have previously been proposed for long-term stable dye-sensitized solar cells (DSSCs). Such redox systems also offer an impressive DSSC performance improvement under light soaking exposure, manifested by an increase in photocurrent and fill factor without the expense of decreasing photovoltage. Kinetic studies show that charge transfer and ion diffusion at the electrode/electrolyte interface are improved due to the light exposure. Control experiments reveal that the light effect is unambiguously associated with electrolyte components, [Co(bpy)(3)](3+) and the Lewis-base additive tert-butylpyridine (TBP). Electrochemical and spectroscopic investigation of the [Co(bpy)(3)](3+)/TBP mixtures points out that the presence of TBP, which retards the electrolyte diffusion, however causes an irreversible redox reaction of [Co(bpy)(3)](3+) upon light exposure that improves the overall conductivity. This discovery not only provides a new strategy to mitigate the typical J(sc)-V-oc trade-off in Co(ii/iii)-mediated DSSCs but also highlights the importance of investigating the photochemistry of a photoelectrochemical system.

  • 10. Goldberg, Kristin
    et al.
    Groombridge, Sam
    Hudson, Julian
    Leach, Andrew G.
    MacFaul, Philip A.
    Pickup, Adrian
    Poultney, Ruth
    Scott, James S.
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Sweeney, Joseph
    Oxadiazole isomers: all bioisosteres are not created equal2012In: MedChemComm, ISSN 2040-2503, E-ISSN 2040-2511, Vol. 3, no 5, p. 600-604Article in journal (Refereed)
    Abstract [en]

    Two series of amino-substituted 1,2,4- and 1,3,4-oxadiazole matched compounds were evaluated and found to have significant differences in their various physical and pharmaceutical properties. Experimental and computational techniques suggested that variation in hydrogen bond acceptor and donor strength were responsible for these effects.

  • 11.
    Gu, Chungang
    et al.
    AstraZeneca, R&D Boston, Waltham, MA USA.;AstraZeneca, R&D Wilmington, Wilmington, DE USA..
    Lewis, Richard J.
    AstraZeneca, R&D Molndal, Molndal, Sweden.;AstraZeneca, R&D Charnwood, Loughborough, Leics, England..
    Wells, Andrew S.
    AstraZeneca, R&D Charnwood, Loughborough, Leics, England..
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry. AstraZeneca, R&D Sodertalje, Sodertalje, Sweden.
    Hosagrahara, Vinayak P.
    AstraZeneca, R&D Boston, Waltham, MA USA..
    Johnsson, Eskil
    AstraZeneca, R&D Molndal, Molndal, Sweden.;AstraZeneca, R&D Lund, Lund, Sweden..
    Hallstrom, Gosta
    AstraZeneca, R&D Lund, Lund, Sweden..
    Lipid Peroxide-Mediated Oxidative Rearrangement of the Pyrazinone Carboxamide Core of Neutrophil Elastase Inhibitor AZD9819 in Blood Plasma Samples2015In: Drug Metabolism And Disposition, ISSN 0090-9556, E-ISSN 1521-009X, Vol. 43, no 10, p. 1441-1449Article in journal (Refereed)
    Abstract [en]

    This study focused on the mechanistic interpretation of ex vivo oxidation of a candidate drug in blood plasma samples. An unexpected lipid peroxide-mediated epoxidation followed by a dramatic rearrangement led to production of a five-membered oxazole derivative from the original six-membered pyrazinone-carboxamide core of a human neutrophil elastase inhibitor, 6-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-N-ethyl-5-methyl-3-oxo-4-(3-(trifluoromethyl) phenyl)-3,4-dihydropyrazine-2-carboxamide (AZD9819). The rearranged oxidation product 2-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-5-(N-ethylacetamido)-N-(3-(trifluoromethyl)phenyl)oxazole-4-carboxamide was characterized by accurate-mass tandem mass spectrometry fragmentations, by two-dimensional NMR and X-ray crystallography of an authentic standard, and by incorporation of an O-18 atom from molecular O-18(2) to the location predicted by our proposed mechanism. The lipid peroxide-mediated oxidation was demonstrated by using human low-density lipoprotein (LDL) in pH 7.4 phosphate buffer and by inhibiting the oxidation with ascorbic acid or L-glutathione, two antioxidants effective in both plasma and the LDL incubation. A nucleophilic mechanism for the epoxidation of AZD9819 by lipid hydroperoxides explains the prevention of its ex vivo oxidation by acidification of the plasma samples. The discovery of the lipid peroxide-dependent oxidation of an analyte and the means of prevention could provide valuable information for biotransformation and bioanalysis.

  • 12.
    Kloo, Lars
    et al.
    KTH, Superseded Departments, Chemistry.
    Rosdahl, Jan
    KTH, Superseded Departments, Chemistry.
    Svensson, Per H.
    KTH, Superseded Departments, Chemistry.
    On the Intra- and Intermolecular Bonding in Polyiodides2002In: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-1948, no 5, p. 1203-1209Article in journal (Refereed)
    Abstract [en]

    The nature of intra- and intermolecular interactions of poly-iodides has been investigated by means of quantum chemical methods and structural statistical data. In the region of "secondary bonds" the interaction is adequately described in terms of covalent bonding accompanied by dispersion. At greater distances the interaction is dominated by ion-quadrupole interactions between ionic and neutral iodine building blocks of the polyiodide structures.

  • 13. Koch, Daniel
    et al.
    Koch, Eva
    Desarbre, Eric
    Stensland, Birgitta
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry. SP Process Development, Sweden.
    Bergman, Jan
    2,2 '-Biindolyl Reactions with Aldehydes2016In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 7, p. 1389-1396Article in journal (Refereed)
    Abstract [en]

    2,2'-Biindolyl has been condensed with aromatic and aliphatic aldehydes and products featuring 10-membered rings have been obtained. Thus, benzaldehyde gave compound 24a as the primary product, which readily underwent transannular oxidative coupling to 25a. The structures of both compounds were confirmed by X-ray crystallography. The product from 2,2'-biindolyl and formaldehyde under strongly acidic conditions was slightly different leading to compound 11, whose structure also was confirmed by X-ray crystallography. In this case, two molecules of 2,2'-biindolyl reacted with six molecules of formaldehyde.

  • 14. Nakhai, Azadeh
    et al.
    Stensland, Birgitta
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Inorganic Chemistry.
    Bergman, Jan
    Synthesis of Benzotriazine and Aryltriazene Derivatives Starting from 2-Azidobenzonitrile Derivatives2010In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 34, p. 6588-6599Article in journal (Refereed)
    Abstract [en]

    3-Substituted 3,4-dihydro-4-imino-1,2,3-benzotriazine derivatives 7 were formed from 2-azidobenzonitriles 4 as starting materials on treatment with Grignard or lithium organic reagents. In some cases these procedures gave aryltriazenes 10 and 11 as products. All compounds were identified by NMR spectroscopy and the structures of three products, namely 7a, 10a and 11i, were corroborated by X-ray crystallography.

  • 15. Pemberton, Nils
    et al.
    Gradén, Henrik
    Evertsson, Emma
    Bratt, Emma
    Lepistö, Matti
    Johannesson, Petra
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Synthesis and Functionalization of Cyclic Sulfonimidamides: A Novel Chiral Heterocyclic Carboxylic Acid Bioisostere2012In: ACS Medicinal Chemistry Letters, ISSN 1948-5875, E-ISSN 1948-5875, Vol. 3, no 7, p. 574-578Article in journal (Refereed)
    Abstract [en]

    An efficient synthesis of aryl substituted cyclic sulfonimidamides designed as chiral nonplanar heterocyclic carboxylic acid bioisosteres is described. The cyclic sulfonimidamide ring system could be prepared in two steps from a trifluoroacetyl protected sulfinamide and methyl ester protected amino acids. By varying the amino acid, a range of different C-3 substituted sulfonimidamides could be prepared. The compounds could be further derivatized in the aryl ring using standard cross coupling reactions to yield highly substituted cyclic sulfonimidamides in excellent yields. The physicochemical properties of the final compounds were examined and compared to those of the corresponding carboxylic acid and tetrazole derivatives. The unique nonplanar shape in combination with the relatively strong acidity (pK(a) 5-6) and the ease of modifying the chemical structure to fine-tune the physicochemical properties suggest that this heterocycle can be a valuable addition to the range of available carboxylic acid isosteres.

  • 16. Pettersson, Birgitta
    et al.
    Bergman, Jan
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Synthetic studies towards 1,5-benzodiazocines2013In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 69, no 12, p. 2647-2654Article in journal (Refereed)
    Abstract [en]

    Anthranilonitrile reacted with phenylmagnesium bromide to yield a dianion, which when heated (similar to 120 degrees C) yielded the condensation product 2-(2-aminophenyl)-2,4-dipheny1-1,2-dihydroquinazoline 8. This heterocycle, when treated with palladium acetate, was converted into 6,12-diphenyldibenzo[b,f][1,5] diazocine 9. Methylmagnesium bromide and anthranilonitrile, under similar conditions directly gave a nitrogen-bridged diazocine, whose structure was determined by X-ray crystallography and also proven to be an analogue of Troger's base. Acid-induced condensation of 2-amino-3-methoxybenzaldehyde gave the trimeric product 45 rather than a dibenzo[b,f][1,5]diazocine.

  • 17. Plowright, Alleyn T.
    et al.
    Barton, Peter
    Bennett, Stuart
    Birch, Alan M.
    Birtles, Susan
    Buckett, Linda K.
    Butlin, Roger J.
    Davies, Robert D. M.
    Ertan, Anne
    Gutierrez, Pablo Morentin
    Kemmitt, Paul D.
    Leach, Andrew G.
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Turnbull, Andrew V.
    Waring, Michael J.
    Design and synthesis of a novel series of cyclohexyloxy-pyridyl derivatives as inhibitors of diacylglycerol acyl transferase 12013In: MedChemComm, ISSN 2040-2503, E-ISSN 2040-2511, Vol. 4, no 1, p. 151-158Article in journal (Refereed)
    Abstract [en]

    A novel series of potent diacylglycerol acyl transferase 1 inhibitors was developed from the clinical candidate AZD3988. Replacement of the phenyl cyclohexyl-ethanoate side chain with substituted oxy-linked side chains to introduce changes in shape and polarity, reduce lipophilicity and mask the hydrogen bond donors with internal hydrogen bond acceptors led to improvements in solubility, unbound clearance and excellent selectivity over the related enzyme acyl-coenzyme A:cholesterol acyltransferase 1. A comparison of the small molecule crystal structures of compound 4 and compound 28 is described. Compounds in this series have good ADMET properties and provide an exposure-dependent decrease in circulating plasma triglyceride levels in a rat oral lipid tolerance test.

  • 18. Privalov, Timofei
    et al.
    Boschloo, Gerrit
    Hagfeldt, Anders
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Inorganic Chemistry.
    Kloo, Lars A.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Inorganic Chemistry.
    A Study of the Interactions between I-/I-3(-) Redox Mediators and Organometallic Sensitizing Dyes in Solar Cells2009In: The Journal of Physical Chemistry C, ISSN 1932-7447, E-ISSN 1932-7455, Vol. 113, no 2, p. 783-790Article in journal (Refereed)
    Abstract [en]

    Specific interactions of the I-/I-3(-) redox mediators with the reduced and oxidized dye, Ru(4,4'-dicarboxy2,2'-bipyridyl)(2)(NCS)(2), referred to as N3 or Ru(dcbpy)(2)(NCS)(2), have been studied by means of density functional theory (DFT) with the focus on the charge transfer process involving {dye(+) I-} adducts; computations had been performed with a series of density functionals (gradient-corrected density functional BP86, and the hybrid density functionals B3LYP, MPW1K, B3PW1K, and MPW1PW91). Different pathways leading to (dye(+) I-) adducts have been studied. First, mechanistic insights into the interaction of I- with Ru-III (dcbpy)(2)(NCS)(2) via an SCN- ligand directly giving rise to Ru-II(dcbpy)(2)(NCS)(2)I](0) have been obtained with the distinctive S-I bonding. Second, the binding of I- to the N3 dye cation via I(-)dcbpy interactions has been analyzed. We also report experimental and computational evidence that sheds light on the interaction of the redox mediator with bipyridyl moieties. Evidence for a charge transfer process in the presence of only one I- anion in the outer coordination sphere of the ruthenium center has been identified. Finally, geometries and electronic structures of plausible intermediates have been computationally analyzed based on an innersphere interaction between the metal center and the redox mediator, including a two-step regeneration reaction: Ru-III (dcbPy)(2)(NCS)(2)](+) + I- -> Ru-III(dcbpy)(2)(NCS)I](+) + SCN-, followed by the interaction of a second I- with the intermediate Ru-III(dcbpy)(2)(NCS)I](+) complex. Conclusive evidence of a charge-transfer process that gives rise to the regenerated Ru-II complex, where I- interacts with the intermediate Ru-III (dcbpy)(2)(NCS)I](+) complex has been identified.

  • 19.
    Ren, Yansong
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Svensson, Per H.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry. RISE Biosci & Mat, Res Inst Sweden, Forskargatan 18, S-15136 Sodertalje, Sweden..
    Ramström, Olof
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry. Department of Chemistry, University of Massachusetts Lowell, 1 University Avenue, Lowell, MA, United States.
    A Multicontrolled Enamine Configurational Switch Undergoing Dynamic Constitutional Exchange2018In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 57, no 21, p. 6256-6260Article in journal (Refereed)
    Abstract [en]

    A multiresponsive enamine-based molecular switch is presented, in which forward/backward configurational rotation around the C=C bond could be precisely controlled by the addition of an acid/base or metal ions. Fluorescence turn-on/off effects and large Stokes shifts were observed while regulating the switching process with Cu-II. The enamine functionality furthermore enabled double dynamic regimes, in which configurational switching could operate in conjunction with constitutional enamine exchange of the rotor part. This behavior was used to construct a prototypical dynamic covalent switch system through enamine exchange with primary amines. The dynamic exchange process could be readily turned on/off by regulating the switch status with pH.

  • 20.
    Safdari, Majid
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Phuyal, D.
    Philippe, B.
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry. SP Process Development, Sweden.
    Butorin, S. M.
    Kvashnina, K. O.
    Rensmo, H.
    Kloo, Lars
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Gardner, James M.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Impact of synthetic routes on the structural and physical properties of butyl-1,4-diammonium lead iodide semiconductors2017In: Journal of Materials Chemistry A, ISSN 2050-7488, Vol. 5, no 23, p. 11730-11738Article in journal (Refereed)
    Abstract [en]

    We report the significant role of synthetic routes and the importance of solvents in the synthesis of organic-inorganic lead iodide materials. Through one route, the intercalation of dimethylformamide in the crystal structure was observed leading to a one-dimensional (1D) [NH3(CH2)4NH3]Pb2I6 structure of the product. This product was compared with the two-dimensional (2D) [NH3(CH2)4NH3]PbI4 recovered from aqueous solvent based synthesis with the same precursors. UV-visible absorption spectroscopy showed a red-shift of 0.1 eV for the band gap of the 1D network in relation to the 2D system. This shift primarily originates from a shift in the valence band edge as determined from photoelectron-and X-ray spectroscopy results. These findings also suggest the iodide 5p orbital as the principal component in the density of states in the valence band edge. Single crystal data show a change in the local coordination around iodide, while in both materials, lead atoms are surrounded by iodide atoms in octahedral units. The conductivity of the one-dimensional material ([NH3(CH2)4NH3]Pb2I6) was 50% of the two-dimensional material ([NH3(CH2)4NH3]PbI4). The fabricated solar cells reflect these changes in the chemical and electronic structure of both materials, although the total light conversion efficiencies of solar cells based on both products were similar.

  • 21.
    Safdari, Majid
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Phuyal, Dibya
    Philippe, Bertrand
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry. SP Process Development, Sweden .
    Butorin, Sergei M.
    Kvashnina, Kristina O.
    Rensmo, Håkan
    Kloo, Lars
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Gardner, James M.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Impact of Synthetic Route on Structural and Physical Properties of Butyl-1,4-Diammonium Lead Iodide Semiconductors2017In: Journal of Materials Chemistry A, ISSN 2050-7488Article in journal (Refereed)
  • 22.
    Safdari, Majid
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry. SP Process Development, Sweden.
    Hoang, Minh Tam
    Oh, Ilwhan
    Kloo, Lars
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Gardner, James M.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Layered 2D alkyldiammonium lead iodide perovskites: synthesis, characterization, and use in solar cells2016In: Journal of Materials Chemistry A, ISSN 2050-7488, Vol. 4, no 40, p. 15638-15646Article in journal (Refereed)
    Abstract [en]

    The synthetic route and properties of three 2D hybrid organic/inorganic lead iodide perovskite materials are reported. The 2D perovskites were synthesized from the reaction between PbI2 and the di-cations of 1,4-diaminobutane, 1,6-diaminohexane, and 1,8-diaminooctane. The resulting products were [NH3(CH2)(4)NH3] PbI4 (BdAPbI(4)), [NH3(CH2)(6)NH3]PbI4 (HdAPbI(4)), and [NH3(CH2)(8)NH3]PbI4 (OdAPbI(4)). Structural characterization shows that two dimensional perovskite structures were formed with inorganic structural planes separated by organic layers. Absorption spectra show band gaps of 2.37 eV (BdAPbI(4)), 2.44 eV (HdAPbI(4)), and 2.55 eV (OdAPbI(4)). The 2D perovskite materials were investigated as light absorbing materials in solid state solar cells. The best performing material under moist, ambient conditions was BdAPbI4 (1.08% efficiency), which was comparable to methylammonium Pb(II) iodide (MAPbI(3)) solar cells (2.1% efficiency) manufactured and studied under analogous conditions. When compared to MAPbI(3), the 2D materials have larger band gaps and lower photoconductivity, while BdAPbI(4) based solar cells shows a comparable absorbed photon-to-current efficiency as compared to MAPbI(3) based ones.

  • 23. Scott, James S.
    et al.
    Birch, Alan M.
    Brocklehurst, Katy J.
    Brown, Hayley S.
    Goldberg, Kristin
    Groombridge, Sam D.
    Hudson, Julian A.
    Leach, Andrew G.
    MacFaul, Philip A.
    McKerrecher, Darren
    Poultney, Ruth
    Schofield, Paul
    Svensson, Per H.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Applied Physical Chemistry.
    Optimisation of aqueous solubility in a series of G protein coupled receptor 119 (GPR119) agonists2013In: MedChemComm, ISSN 2040-2503, E-ISSN 2040-2511, Vol. 4, no 1, p. 95-100Article in journal (Refereed)
    Abstract [en]

    Improving aqueous solubility is a challenge frequently faced within drug discovery programs. Herein we describe increases in solubility in two sub-series of GPR119 agonists through reduction of lipophilicity together with hydrogen bond acceptor modulation. Small molecule X-ray crystallography was utilised to investigate effects on solid state interactions.

  • 24.
    Starkholm, Allan
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Applied Physical Chemistry.
    Kloo, Lars
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Applied Physical Chemistry.
    Svensson, Per H.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Applied Physical Chemistry.
    Polyiodide Hybrid Perovskites: A Strategy To Convert Intrinsic 2D Systems into 3D Photovoltaic Materials2019In: ACS Applied Energy Materials, ISSN 2574-0962, Vol. 2, no 1, p. 477-485Article in journal (Refereed)
    Abstract [en]

    Two new organic inorganic hybrid perovskite compounds, (Me3S)(2)Pb5I14*2I(2) (1) and (C8H11S)(2)Pb2I6*I-2 (2), have been synthesized and subsequently characterized in this study. The materials were synthesized from facile one-pot, one-step reactions of lead iodide, corresponding sulfide, methanol, iodine, and hydroiodic acid in the case of 2. Structural analysis reveals the presence of polyiodide entities in both compounds. Compound 1 contains triiodide anions, I-3(-), that are uniquely shared between the 2D inorganic slabs, forming a 3D network. Both 1 and 2 have I-2 molecules that are bridging the inorganic slabs through a structural motif that can be regarded as a tetraiodide anion, I-4(2-). Optical spectroscopy shows band gaps of 1.86 eV for 1 and 1.89 eV for 2. The optoelectronic properties were further investigated with band structure calculations. Single-crystal IV-characteristics of 1 show that the compound is photoactive confirming it as a promising photovoltaic candidate. Compound 1 highlights a novel strategy of designing 3D semiconducting hybrid materials by incorporating polyiodides to provide direct geometric and electronic connections between the semiconducting inorganic perovskite sheets.

1 - 24 of 24
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