Synthesis and photochromic properties of spiro[naphthopyran-7′H- benzocyclohepta-5′,8′-dienes]

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A series of spironaphthopyrans has been synthesised by the acid-catalysed condensation between either a substituted 1-naphthol or 2-naphthol and the propargylic alcohol derived from the addition of lithium trimethylsilylacetylide to a 7H-benzocycloheptan-7-one with subsequent in situ silyl group removal. The photochromism of the novel spironaphthopyrans was characterised by a bathochromically shifted λ max coupled with a relatively quick initial fade of the photogenerated species relative to the comparable diphenyl substituted model compounds. After initial fading a relatively intense residual colour persisted for the spironaphthopyrans.

LanguageEnglish
Pages62-68
Number of pages7
JournalDyes and Pigments
Volume95
Issue number1
DOIs
Publication statusPublished - 1 Oct 2012
Externally publishedYes

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Photochromism
Naphthol
Lithium
Condensation
Alcohols
Color
Acids
2-naphthol
1-naphthol
diphenyl

Cite this

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title = "Synthesis and photochromic properties of spiro[naphthopyran-7′H- benzocyclohepta-5′,8′-dienes]",
abstract = "A series of spironaphthopyrans has been synthesised by the acid-catalysed condensation between either a substituted 1-naphthol or 2-naphthol and the propargylic alcohol derived from the addition of lithium trimethylsilylacetylide to a 7H-benzocycloheptan-7-one with subsequent in situ silyl group removal. The photochromism of the novel spironaphthopyrans was characterised by a bathochromically shifted λ max coupled with a relatively quick initial fade of the photogenerated species relative to the comparable diphenyl substituted model compounds. After initial fading a relatively intense residual colour persisted for the spironaphthopyrans.",
keywords = "Benzocycloheptanone, Naphthopyran, Photochromism, Propynol, Spiropyran, Synthesis",
author = "Crossley, {Daniel L.} and Gabbutt, {Christopher D.} and {Mark Heron}, B. and Paul Kay and Martin Mogstad",
year = "2012",
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doi = "10.1016/j.dyepig.2012.03.031",
language = "English",
volume = "95",
pages = "62--68",
journal = "Dyes and Pigments",
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Synthesis and photochromic properties of spiro[naphthopyran-7′H- benzocyclohepta-5′,8′-dienes]. / Crossley, Daniel L.; Gabbutt, Christopher D.; Mark Heron, B.; Kay, Paul; Mogstad, Martin.

In: Dyes and Pigments, Vol. 95, No. 1, 01.10.2012, p. 62-68.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis and photochromic properties of spiro[naphthopyran-7′H- benzocyclohepta-5′,8′-dienes]

AU - Crossley, Daniel L.

AU - Gabbutt, Christopher D.

AU - Mark Heron, B.

AU - Kay, Paul

AU - Mogstad, Martin

PY - 2012/10/1

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N2 - A series of spironaphthopyrans has been synthesised by the acid-catalysed condensation between either a substituted 1-naphthol or 2-naphthol and the propargylic alcohol derived from the addition of lithium trimethylsilylacetylide to a 7H-benzocycloheptan-7-one with subsequent in situ silyl group removal. The photochromism of the novel spironaphthopyrans was characterised by a bathochromically shifted λ max coupled with a relatively quick initial fade of the photogenerated species relative to the comparable diphenyl substituted model compounds. After initial fading a relatively intense residual colour persisted for the spironaphthopyrans.

AB - A series of spironaphthopyrans has been synthesised by the acid-catalysed condensation between either a substituted 1-naphthol or 2-naphthol and the propargylic alcohol derived from the addition of lithium trimethylsilylacetylide to a 7H-benzocycloheptan-7-one with subsequent in situ silyl group removal. The photochromism of the novel spironaphthopyrans was characterised by a bathochromically shifted λ max coupled with a relatively quick initial fade of the photogenerated species relative to the comparable diphenyl substituted model compounds. After initial fading a relatively intense residual colour persisted for the spironaphthopyrans.

KW - Benzocycloheptanone

KW - Naphthopyran

KW - Photochromism

KW - Propynol

KW - Spiropyran

KW - Synthesis

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