Abstract
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.
Original language | English |
---|---|
Pages (from-to) | 9352-9358 |
Number of pages | 7 |
Journal | Tetrahedron |
Volume | 70 |
Issue number | 49 |
Early online date | 23 Oct 2014 |
DOIs | |
Publication status | Published - 9 Dec 2014 |
Fingerprint
Dive into the research topics of '5-Hydroxy substituted naphthofurans and naphthothiazoles as precursors of photochromic benzochromenes'. Together they form a unique fingerprint.Profiles
-
Stuart Aiken
- Department of Chemical Sciences - Senior Research Fellow
- School of Applied Sciences
- Centre for Functional Materials - Member
Person: Academic