Showing papers by "Sergey Sergeyev published in 2010"
TL;DR: The joint theoretical and experimental studies of chromophores derived from Tröger's base skeleton, in comparison with benchmarkchromophores featuring a dimethylamino group as the donor, provided insight into the relationship between the structure of the new Chromophores and their NLO properties.
Abstract: We report on the novel chiral push pull chromophores derived from 6H,12H-5,11-methanodibenzo-[b,f][1,5]diazocine (Troger's base skeleton). The synthesis of symmetrical chromophores featuring two identical acceptors, as well as the synthesis of unsymmetrical chromophores featuring only one acceptor is given. Symmetrical chromophores were prepared in the enantiomerically pure form and their chiroptical properties were investigated. Second-order nonlinear optical (NLO) properties of new chromophores were investigated with the aid of hyper-Rayleigh scattering (HRS). The detailed theoretical analysis of the second-order NLO properties of the chromophores was also undertaken. The joint theoretical and experimental studies of chromophores derived from Trager's base skeleton, in comparison with benchmark chromophores featuring a dimethylamino group as the donor, provided insight into the relationship between the structure of the new chromophores and their NLO properties.
53 citations
TL;DR: In this paper, an easily applicable method for the synthesis of diketopyrrolopyrrole derivatives comprising bithiophene moieties, with different substituents on the nitrogen atoms (Me, n-octyl, 3,5-di-tert-butylbenzyl, Boc) and on the thiophene rings (C6H13, C12H25), in good yields and purities.
52 citations
TL;DR: The self-assembly of functional polythiophenes was studied by a bottom-up approach "from molecule to polymer" and indirect proof of well-defined nanostructured organization was provided by the partial photocyclization of pendant styryl moieties under UV irradiation.
Abstract: The self-assembly of functional polythiophenes was studied by a bottom-up approach "from molecule to polymer". The synthesis and the X-ray structure of 2,5-dibromo-3-styryl and 3-2',3',4',5',6'-pentafluorostyryl-thiophenes revealed a supramolecular arrangement controlled by pi-pi interactions between the aromatic rings. A [2 + 2] photocyclization reaction in the solid state of (E)-1-2',5'-dibromo-3'-thienyl-2-pentafluorophenylethene triggers the formation of a rare cycloadduct comprising thiophene rings. The X-ray analysis confirmed its rctt stereochemistry. The synthesis of P3HT-b-P3ST and P3HT-b-P3STF block oligomers was achieved by a GRIM method in good yields. An indirect proof of well-defined nanostructured organization was provided by the partial photocyclization of pendant styryl moieties under UV irradiation.
43 citations
TL;DR: In this paper, the synthesis and characterization of twelve new soluble oligothiophenes, possessing two to four 3,4-dicyanothiophene units in their backbone, are described.
14 citations
TL;DR: Crystal structures of Tröger's base analogues with the methyl groups replaced by ethyl, iso-propyl and tert-butyl groups were studied and the incidence of Z' > 1 structures increases to rather conspicuous levels.
Abstract: Crystal structures of Trogers base (5,11-methano-2,8-dimethyl-5,6,11, 12-tetrahydrodibenzo[b,f][1,5]diazocine) analogues with the methyl groups replaced by ethyl, iso-propyl and tert-butyl groups were studied. The incidence of Z′ > 1 structures increases to rather conspicuous levels. The reasons behind this trend are expanded upon, and a possible explanation is given in the flexibility of the alkyl substituents and van der Waals stabilization. In combination these effects allow for an additional stabilization of the packing by small changes in the molecular conformations, thus expanding the size of the asymmetric unit. © 2010 International Union of Crystallography Printed in Singapore - all rights reserved.
11 citations