Selivanova Daria G, Gorbunov Alexei A, Mayorova Olga A, Vasyanin Alexander N, Lunegov Igor V, Shklyaeva Elena V, Abashev Georgii G
Laboratory of Active Reagents Synthesis, Institute of Technical Chemistry, Russian Academy of Sciences, Ural Division, Academician Korolev street, 3, 614990, Perm, Russia.
Department of Analytical Chemistry, Perm State University, Bukirev street, 15, 614990, Perm, Russia.
Beilstein J Org Chem. 2017 Aug 10;13:1583-1595. doi: 10.3762/bjoc.13.158. eCollection 2017.
In this paper we present a synthetic approach to six new D-π-A-D conjugated chromophores containing the -[ω-(4-methoxyphenoxy)alkyl]carbazole fragment. Such readily functionalizable heterocycle as carbazole was used as a main starting compound for their preparation. The investigation of the optical properties has shown that the positive solvatochromism is inherent to the chromophores containing an electron-withdrawing prop-2-en-1-one fragment, while the compounds containing a 2-aminopyrimidine moiety exhibit both positive and negative solvatochromism. The fluorescence quantum yields were experimentally determined for some of the synthesized chromophores; e.g., 1-(5-arylthiophen-2-yl)ethanones quantum yields were found to lie in an interval of 60-80%. Electrochemical oxidation of the synthesized chromophores has resulted in the formation of colored thin oligomeric films that became possible due to the presence of carbazole or pyrrole fragments with free electron-rich positions.
在本文中，我们提出了一种合成方法，用于制备六种含有-[ω-(4-甲氧基苯氧基)烷基]咔唑片段的新型D-π-A-D共轭发色团。咔唑这种易于官能化的杂环被用作制备它们的主要起始化合物。光学性质研究表明，含有吸电子的丙-2-烯-1-酮片段的发色团具有正溶剂化显色性，而含有2-氨基嘧啶部分的化合物则表现出正溶剂化显色性和负溶剂化显色性。通过实验测定了一些合成发色团的荧光量子产率；例如，发现1-(5-芳基噻吩-2-基)乙酮的量子产率在60%-80%的范围内。合成发色团的电化学氧化导致形成了有色的薄寡聚膜，这是由于存在具有富电子自由位置的咔唑或吡咯片段才得以实现的。
