Photochromic bi-naphthopyrans

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Abstract

A series of novel 3-aryl-(3,3-diaryl-3H-naphtho[2,1-b]pyran-8-yl)-3H-naphtho[2,1-b]pyrans has been accessed from 6-bromo-2-naphthol via a four step transformation. Acylation of the dianion derived from the treatment of 6-bromo-2-naphthol with n-butyllithium with Weinreb amides and subsequent reaction with a 1,1,-diarylprop-2-yn-1-ol gave 8-aroyl-3H-naphtho[2,1-b]pyrans in good yield. Addition of lithium trimethylsilylacetylide to the foregoing 8-aroylnaphthopyrans proceeded smoothly with base-mediated desilyation to afford the target bi-naphthopyrans upon acid-catalysed reaction with 2-naphthol. Preliminary evaluation of the photochromic response of the new bi-naphthopyrans revealed reversible independent naphthopyran ring-opening leading to a complex photochromic signature.

LanguageEnglish
Pages239-250
Number of pages12
JournalDyes and Pigments
Volume113
DOIs
Publication statusPublished - 2015

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Naphthol
Acylation
Lithium
Amides
Acids
naphtho(2,1-b)pyran
6-bromo-2-naphthol

Cite this

@article{111a43a61d2c4fc4b8107b669ec67d5f,
title = "Photochromic bi-naphthopyrans",
abstract = "A series of novel 3-aryl-(3,3-diaryl-3H-naphtho[2,1-b]pyran-8-yl)-3H-naphtho[2,1-b]pyrans has been accessed from 6-bromo-2-naphthol via a four step transformation. Acylation of the dianion derived from the treatment of 6-bromo-2-naphthol with n-butyllithium with Weinreb amides and subsequent reaction with a 1,1,-diarylprop-2-yn-1-ol gave 8-aroyl-3H-naphtho[2,1-b]pyrans in good yield. Addition of lithium trimethylsilylacetylide to the foregoing 8-aroylnaphthopyrans proceeded smoothly with base-mediated desilyation to afford the target bi-naphthopyrans upon acid-catalysed reaction with 2-naphthol. Preliminary evaluation of the photochromic response of the new bi-naphthopyrans revealed reversible independent naphthopyran ring-opening leading to a complex photochromic signature.",
keywords = "Bi-naphthopyran, Functional dye, Naphthopyran, Photochromism, Synthesis, Weinreb amide",
author = "Stuart Aiken and Gabbutt, {Christopher D.} and Heron, {B. Mark} and Kolla, {Suresh B.}",
year = "2015",
doi = "10.1016/j.dyepig.2014.08.018",
language = "English",
volume = "113",
pages = "239--250",
journal = "Dyes and Pigments",
issn = "0143-7208",
publisher = "Elsevier BV",

}

Photochromic bi-naphthopyrans. / Aiken, Stuart; Gabbutt, Christopher D.; Heron, B. Mark; Kolla, Suresh B.

In: Dyes and Pigments, Vol. 113, 2015, p. 239-250.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Photochromic bi-naphthopyrans

AU - Aiken,Stuart

AU - Gabbutt,Christopher D.

AU - Heron,B. Mark

AU - Kolla,Suresh B.

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N2 - A series of novel 3-aryl-(3,3-diaryl-3H-naphtho[2,1-b]pyran-8-yl)-3H-naphtho[2,1-b]pyrans has been accessed from 6-bromo-2-naphthol via a four step transformation. Acylation of the dianion derived from the treatment of 6-bromo-2-naphthol with n-butyllithium with Weinreb amides and subsequent reaction with a 1,1,-diarylprop-2-yn-1-ol gave 8-aroyl-3H-naphtho[2,1-b]pyrans in good yield. Addition of lithium trimethylsilylacetylide to the foregoing 8-aroylnaphthopyrans proceeded smoothly with base-mediated desilyation to afford the target bi-naphthopyrans upon acid-catalysed reaction with 2-naphthol. Preliminary evaluation of the photochromic response of the new bi-naphthopyrans revealed reversible independent naphthopyran ring-opening leading to a complex photochromic signature.

AB - A series of novel 3-aryl-(3,3-diaryl-3H-naphtho[2,1-b]pyran-8-yl)-3H-naphtho[2,1-b]pyrans has been accessed from 6-bromo-2-naphthol via a four step transformation. Acylation of the dianion derived from the treatment of 6-bromo-2-naphthol with n-butyllithium with Weinreb amides and subsequent reaction with a 1,1,-diarylprop-2-yn-1-ol gave 8-aroyl-3H-naphtho[2,1-b]pyrans in good yield. Addition of lithium trimethylsilylacetylide to the foregoing 8-aroylnaphthopyrans proceeded smoothly with base-mediated desilyation to afford the target bi-naphthopyrans upon acid-catalysed reaction with 2-naphthol. Preliminary evaluation of the photochromic response of the new bi-naphthopyrans revealed reversible independent naphthopyran ring-opening leading to a complex photochromic signature.

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KW - Functional dye

KW - Naphthopyran

KW - Photochromism

KW - Synthesis

KW - Weinreb amide

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