کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5216259 1383257 2014 7 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
5-Hydroxy substituted naphthofurans and naphthothiazoles as precursors of photochromic benzochromenes
ترجمه فارسی عنوان
5-هیدروکسی جایگزین نفتوفورانها و نفتتوتیازولها به عنوان پیشکسرهای بنزوکرومنهای فلوکرومیک
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
چکیده انگلیسی

3-Benzoylnaphtho[1,2-b]furan-5-ol forms a photochromic benzochromene upon reaction with a 1,1-diarylprop-2-yn-1-ol affording a red coloured photomerocyanine, with a half-life of 2.3 min, upon UV-irradiation. Retention of the initial 1,4-oxygenation pattern of the naphthalene moiety through replacement of the furan unit with a methoxy group led to a benzochromene, which developed a similar red colour upon UV-irradiation but was more persistent with a half-life of over 42 min. Treatment of the 3-benzoylnaphtho[1,2-b]furan-5-ol with a 1,1,3-triarylprop-2-yn-1-ol similarly afforded a benzochromene, which did not display any photochromism at ambient temperature as a consequence of steric interactions in the photomerocyanines. The synthesis of N-(5-hydroxynaphtho[1,2-d]thiazol-2-yl)acetamide, as a precursor to a photochromic hetero-fused benzochromene, by the mild selective deprotection of the O-acetyl group of 2-acetamidonaphtho[1,2-d]thiazol-5-yl acetate was complicated by a facile, competitive, oxidative dimerisation to afford a novel [2,2′-binaphthothiazole]-1,1′-diol.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 70, Issue 49, 9 December 2014, Pages 9352–9358