کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1410606 1501873 2008 7 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
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
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
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
چکیده انگلیسی

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′-dione and 3: trans-syn-3,3′-(2-thienyl)-3,3′-dihydroxy-[2,2′-bi-1H-indene]-1,1′-dione) 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, 1H NMR, MS, elemental analysis, and X-ray crystallography. The photochromic and photo-induced 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 1 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.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Molecular Structure - Volume 891, Issues 1–3, 26 November 2008, Pages 214–220
نویسندگان
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