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For the first time, syntheses of 1,3-diarylbenzo[c]selenophenes are reported involving a selenium transfer reaction of keto-alcohol/benzo[c]furan using Woollins reagent. 相似文献
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For seeking high‐efficiency narrow‐band‐gap donor materials to enhance short‐circuit current density for organic solar cells, a series of oligo‐selenophene (OS) and oligo(3,4‐ethylenedioxyselenophene) (OEDOS) with various chain lengths were designed and characterized using density functional theory (DFT) and time‐dependent DFT calculations. Based on the results, it can be seen that with increasing chain length of the oligomers in both syn‐ and anti‐adding manners, the bond length alternation is decreased which indicates that the π‐electron delocalization is increased. Also, when the chain length is increased the electronic energy gap and the optical energy gap are decreased. It can be concluded that the syn‐(OS)n=10,14,15, anti‐(OS)n=14 and anti‐(OEDOS)n=7–12 oligomers can act as low‐band‐gap polymers. Therefore they can absorb more sunlight based on maximum wavelength (higher than 620 nm). Furthermore, a red shift in the simulated absorption spectra of (OS)n and (OEDOS)n donors is observed. It is found that (OS)n=14,15 with syn configuration of the extended oligomers is the most suitable donor for the design of high‐performance organic solar cells possessing a narrow electronic band gap, high exciton lifetime and broad and intense absorption spectra that cover the solar spectrum leading to complete light‐harvesting efficiency. 相似文献
3.
Ivaylo K. Ivanov 《合成通讯》2013,43(6):800-809
Diphenyl 3-methyl-penta-1,2,4-trienyl phosphine oxide can be readily prepared via an atom-economical [2,3]-sigmatropic rearrangement of the mediated alkenynyl phosphinite formed in situ by reaction of 3-methylpent-1-en-4-yn-3-ol with diphenylchlorophosphine. Electrophilic cyclization reactions of the vinylallenyl phosphine oxide prepared were investigated as it was established that the reactions proceeded with formation of various heterocyclic or highly unsaturated compounds with participation of the allenic and/or 1,3-dienic part of the vinylallenic system with neighboring group participation of phosphoryl and/or vinylic group. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file. 相似文献
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Yury Yu. Rusakov Leonid B. Krivdin Stephan P. A. Sauer Ekaterina P. Levanova Galina G. Levkovskaya 《Magnetic resonance in chemistry : MRC》2010,48(1):44-52
Experimental measurements and second‐order polarization propagator approach (SOPPA) calculations of 77Se? 1H spin–spin coupling constants together with theoretical energy‐based conformational analysis in the series of 2‐substituted selenophenes have been carried out. A new basis set optimized for the calculation of 77Se? 1H spin–spin coupling constants has been introduced by extending the aug‐cc‐pVTZ‐J basis for selenium. Most of the spin–spin coupling constants under study, especially vicinal 77Se? 1H couplings, demonstrated a remarkable stereochemical behavior with respect to the internal rotation of the substituent in the 2‐position of the selenophene ring, which is of major importance in the stereochemical studies of the related organoselenium compounds. Copyright © 2009 John Wiley & Sons, Ltd. 相似文献
6.
E. Lukevics P. Arsenyan S. Belyakov O. Pudova 《Chemistry of Heterocyclic Compounds》2002,38(7):763-777
The results of X-ray diffraction investigations of compounds containing selenophene and tellurophene fragments are reviewed and analyzed. The structural features of unsubstituted selenophene and tellurophene and their mono-, di-, tri-, and tetrasubstituted derivatives and also the structure of the complexes of selenophenes and tellurophenes with transition metals are discussed. 相似文献
7.
Zahra Siroos Mohammad H. Mosslemin 《Phosphorus, sulfur, and silicon and the related elements》2020,195(10):877-880
AbstractReaction between arylidenemalononitriles and dimethyl acetylenedicarboxylate in the presence of KSeCN at room temperature provided a simple and efficient one-pot route for the synthesis of highly functionalized selenophenes. The reaction is characterized by mild conditions, short reaction time, and tolerance to various functional groups. 相似文献
8.
Arasambattu K. Mohanakrishnan Natarajan Senthil Kumar P. Amaladass 《Tetrahedron letters》2008,49(32):4792-4795
The synthesis of soluble benzo[c]thiophene analogs capped with 9,9-dialkylfluorene at one end is described. 相似文献
9.
The relative reactivity (substrate selectivity) of five-membered heterocycles on electrophilic substitution (pyrrole >> furan > selenophene > thiophene) and their positional selectivity (furan > selenophene thiophene > pyrrole) are not consistent. The indicated differences in positional selectivity ( : ratios) of the parent heterocycles show up essentially in orientation on electrophilic substitution reactions of their derivatives and the corresponding benzannelated systems. It was shown that the positional selectivity was reduced in a sequence corresponding to the change in relative stability of the onium states of the elements (O+ < Se+ S+ < N+) and reflects the predominant role of the heteroatoms in stabilizing the -complexes formed on -substitution, in which the positive charge is distributed between the heteroatom and one -carbon atom (in -isom ers four atoms of the ring participate in delocalization of the charge). This interpretation was confirmed by quantum-chemical calculations carried out by the RHF/6-31G(d), MP2/6-31G(d)//RHF(6)-31G(d), and B3LYP/6-31G(d) ab initio methods. 相似文献
10.
Nam‐Ho You Namiko Fukuzaki Yasuo Suzuki Yasuhiro Nakamura Tomoya Higashihara Shinji Ando Mitsuru Ueda 《Journal of polymer science. Part A, Polymer chemistry》2009,47(17):4428-4434
A highly refractive and transparent aromatic polyimide (PI) containing a selenophene unit has been developed. The PI was prepared by a two‐step polycondensation procedure from 2,5‐bis(4‐aminophenylenesulfanyl)selenophene (APSP) and 4,4′‐[p‐thiobis(phenylenesulfanyl)]diphthalic anhydride (3SDEA), and shows high thermal stabilities, such as a relatively high‐glass transition temperature of 189 °C and 5% weight loss temperature (T5%) of 418 °C. The optical transmittance of the PI film at 450 nm is higher than 50%. The selenophene unit provides the PI with a refractive index of 1.7594, which is higher than corresponding PIs containing a thiophene or a phenyl unit because of the high polarizability per unit volume of the selenium atom. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 4428–4434, 2009 相似文献