The influence of a 1,1-diarylvinyl moiety on the photochromism of naphthopyrans

Gabbutt, Christopher D., Heron, B. Mark, Kilner, Colin and Kolla, Suresh B. (2010) The influence of a 1,1-diarylvinyl moiety on the photochromism of naphthopyrans. Organic & Biomolecular Chemistry, 8 (21). pp. 4874-4883. ISSN 1477-0520

Abstract

1,1,3-Triarylpent-4-en-1-yn-3-ols, efficiently obtained in two steps from 1,1,3-triarylprop-2-yn-1-ols by a Meyer-Schuster rearrangement and subsequent addition of lithium trimethylsilylacetylide, react with either a 1- or 2- naphthol to afford photochromic 1,1-diarylvinyl substituted naphtho[1,2-b]- or naphtho[2,1-b]-pyrans respectively. Irradiation of solutions of these naphthopyrans results in reversible electrocyclic ring-opening to afford photomerocyanines which possess an extended conjugated system and show a bathochromically-shifted λmax relative to the non-vinyl substituted analogues.

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