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5-Hydroxy substituted naphthofurans and naphthothiazoles as precursors of photochromic benzochromenes

Aiken, Stuart, Allsopp, Ben, Booth, Kathryn, Gabbutt, Christopher D. and Heron, B. Mark (2014) 5-Hydroxy substituted naphthofurans and naphthothiazoles as precursors of photochromic benzochromenes. Tetrahedron, 70 (49). pp. 9352-9358. ISSN 0040-4020

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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 UVirradiation.
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 [2,20-binaphthothiazole]-1,10-diol.

Item Type: Article
Subjects: Q Science > QD Chemistry
Schools: School of Applied Sciences
Related URLs:
Depositing User: Mark Heron
Date Deposited: 02 Sep 2015 10:41
Last Modified: 04 Sep 2015 21:17


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