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首页> 外文期刊>Chemistry: A European journal >Conjugated 4-methoxybipyrrole thiophene azomethines: Synthesis, opto-electronic properties, and crystallographic characterization
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Conjugated 4-methoxybipyrrole thiophene azomethines: Synthesis, opto-electronic properties, and crystallographic characterization

机译：共轭4-甲氧基双吡咯噻吩甲亚胺：合成，光电性能和晶体学表征

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摘要

In the search of functional materials with improved electrochromic properties, thiophenes and asymmetric bipyrroles have been conjugated with azomethine units. 4-Methoxy-2,2′-bipyrroles 3-6 were first synthesized by a general route from 4-hydroxyproline and converted subsequently to dialdehydes 8-15, which underwent condensations with different aminothiophenes to provide azomethine conjugates 14-18 and 20-22. The crystallization and X-ray analysis of 20 showed the heterocycles and azomethine bonds were all co-planar with the heterocycles adopting an anti-parallel arrangement. These configurations result in extended conjugation and enhanced opto-electronic properties of the azomethines. Oxidation potential (E_(pa)) was tailored by modification of the substitution pattern of the terminal thiophenes and central pyrroles of the azomethines. The combined low E_(pa) and extended azomethine degree of conjugation resulted in stark color transitions occurring between their neutral and oxidized states. Reversible color formation was induced both electrochemically and by doping/de-doping with trifluoroacetic acid/triethylamine.
机译：在寻找具有改进的电致变色性质的功能材料中，噻吩和不对称联吡咯已经与偶氮甲碱单元共轭。首先通过一般路线由4-羟基脯氨酸合成4-甲氧基-2,2'-联吡咯3-6，然后将其转化为二醛8-15，将其与不同的氨基噻吩缩合以提供偶氮甲碱共轭物14-18和20-22。 。 20的结晶和X射线分析表明，杂环和甲亚胺键均与采用反平行排列的杂环共面。这些配置导致偶氮甲碱的扩展共轭和增强的光电性能。氧化电位（E_（pa））通过修饰末端噻吩和偶氮甲碱的中心吡咯的取代方式进行定制。低的E_（pa）和延长的偶氮甲碱共轭度的结合导致在中性和氧化态之间发生鲜明的颜色过渡。通过电化学以及通过用三氟乙酸/三乙胺进行掺杂/去掺杂，诱导了可逆的颜色形成。

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