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

Christopher D. Gabbutt, B. Mark Heron, Colin Kilner, Suresh B. Kolla

Research output: Contribution to journalArticle

12 Citations (Scopus)

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.

LanguageEnglish
Pages4874-4883
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume8
Issue number21
Early online date16 Aug 2010
DOIs
Publication statusPublished - 7 Nov 2010
Externally publishedYes

Fingerprint

Photochromism
photochromism
Lithium
lithium
Irradiation
analogs
irradiation
rings
1-naphthol
2-naphthol
naphtho(2,1-b)pyran

Cite this

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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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The influence of a 1,1-diarylvinyl moiety on the photochromism of naphthopyrans. / Gabbutt, Christopher D.; Heron, B. Mark; Kilner, Colin; Kolla, Suresh B.

In: Organic and Biomolecular Chemistry, Vol. 8, No. 21, 07.11.2010, p. 4874-4883.

Research output: Contribution to journalArticle

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AU - Heron, B. Mark

AU - Kilner, Colin

AU - Kolla, Suresh B.

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