Photochromic bi-naphthopyrans

Stuart Aiken; Christopher D. Gabbutt; B. Mark Heron; Suresh B. Kolla

doi:10.1016/j.dyepig.2014.08.018

Photochromic bi-naphthopyrans

Stuart Aiken, Christopher D. Gabbutt, B. Mark Heron, Suresh B. Kolla

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

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.

Original language	English
Pages (from-to)	239-250
Number of pages	12
Journal	Dyes and Pigments
Volume	113
Early online date	28 Aug 2014
DOIs	https://doi.org/10.1016/j.dyepig.2014.08.018
Publication status	Published - 1 Feb 2015

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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",

month = feb,

day = "1",

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",

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TY - JOUR

T1 - Photochromic bi-naphthopyrans

AU - Aiken, Stuart

AU - Gabbutt, Christopher D.

AU - Heron, B. Mark

AU - Kolla, Suresh B.

PY - 2015/2/1

Y1 - 2015/2/1

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.

KW - Bi-naphthopyran

KW - Functional dye

KW - Naphthopyran

KW - Photochromism

KW - Synthesis

KW - Weinreb amide

UR - http://www.scopus.com/inward/record.url?scp=84907280976&partnerID=8YFLogxK

U2 - 10.1016/j.dyepig.2014.08.018

DO - 10.1016/j.dyepig.2014.08.018

M3 - Article

AN - SCOPUS:84907280976

SN - 0143-7208

VL - 113

SP - 239

EP - 250

JO - Dyes and Pigments

JF - Dyes and Pigments

ER -

Photochromic bi-naphthopyrans

Abstract

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