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首页> 外文期刊>Journal of Molecular Structure >Synthesis and properties of photochromic biindenylidenedione derivatives containing thiophene groups, and new insights into the reaction of 2,2 '-biindanylidene-1,1 ',3,3 '-tetraone with Grignard reagent
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Synthesis and properties of photochromic biindenylidenedione derivatives containing thiophene groups, and new insights into the reaction of 2,2 '-biindanylidene-1,1 ',3,3 '-tetraone with Grignard reagent

机译：含噻吩基团的光致变色联茚基二烯二酮衍生物的合成和性质，以及对2,2'-联茚亚基-1,1'，3,3'-四酮与格氏试剂反应的新见解

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摘要

Three indenone derivatives (1: 2-[3'-hydroxy-3'-(2-thienyl)indanone-2'-yl]-3-(2-thienyl)indenone; 2: trans-anti-3,3'-(2-thienyl)-3,3'-dihydroxy-[2,2'-bi-1H-indene]-1,1'dion e and 3: trans-syn-3,3'-(2-thienyl)-3,3'-dihydroxy-[2,2'-bi-1H-indene]-1,1'-dion e) were obtained in a one-pot reaction of 2,2'-biindanylidene-1,1',3,3'-tetraone with 2-thienylmagnesium bromide. Their structures were characterized by means of IR, H-1 NMR, MS, elemental analysis, and X-ray crystallography. The photochromic and photoinduced radical behaviors of these compounds were investigated by means of solid UV-vis spectroscopy and electron spin resonance (ESR) spectroscopy. The results show that compounds 2 and 3 exhibit photochromism in the solid state, whereas compound I does not. The relationship between the crystal structures and photochemical properties is also discussed. Based on the formation and product distribution of compounds 1, 2, and 3, a plausible pathway is suggested for the reaction of 2,2'-biindanylidene-1,1',3,3'-tetraone with 2-thienylmagnesium bromide. The findings obtained in this study also provide new insights into the addition-oxidation mechanism for the reaction of 2,2'-biindanylidene-1,1',3,3'-tetraone with Grignard reagent. (C) 2008 Elsevier B.V. All rights reserved.
机译：三种茚满酮衍生物（1：2- [3'-羟基-3'-（2-噻吩基）茚满酮-2'-基] -3-（2-噻吩基）茚满酮; 2：反式-3,3'- （2-噻吩基）-3,3'-二羟基-[2,2'-bi-1H-茚] -1,1'dion e和3：反式-syn-3,3'-（2-噻吩基）-在2,2'-双茚并亚基-1,1'，3的一锅反应中获得了3,3'-二羟基-[2,2'-bi-1H-茚] -1,1'-dion e）。 ，3′-四酮与2-噻吩基溴化镁。通过IR，H-1 NMR，MS，元素分析和X射线晶体学对它们的结构进行了表征。通过固体紫外可见光谱和电子自旋共振（ESR）光谱研究了这些化合物的光致变色和光诱导的自由基行为。结果表明，化合物2和3在固态下表现出光致变色，而化合物I则没有。还讨论了晶体结构与光化学性质之间的关系。根据化合物1、2和3的形成和产物分布，提出了2,2'-双茚并亚基-1,1'，3,3'-四酮与2-噻吩基溴化镁反应的可能途径。在这项研究中获得的发现也为2，2'-联茚二亚基-1,1'，3,3'-四酮与格利雅试剂的反应提供了新的见解。 （C）2008 Elsevier B.V.保留所有权利。

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