The intramolecular capture of thermally generated merocyanine dyes derived from naphthopyrans

Photochromism of 5-(diarylhydroxymethyl)-2H-naphtho[1,2-b] pyrans

Christopher D. Gabbutt, Lucy V. Gibbons, B. Mark Heron, Suresh B. Kolla

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A series of 2H-naphtho[1,2-b]pyrans bearing a diarylmethanol unit at C-5 have been synthesised by the addition of an excess of an aryllithium reagent to alkyl 2H-naphtho[1,2-b]pyran-5-carboxylate precursors. These naphthopyrans show photochromism when exposed to ultraviolet irradiation and also generate intense colours at low pH through triarylmethine cation generation. However, photochromism of the triarylmethine cation derived from the naphthopyran unit could not be detected. An irreversible cascade process initiated by the thermally-induced ring-opening of the diarylmethanol substituted 2H-naphtho[1,2-b]pyrans in the presence of an acid catalyst afforded novel benzopentalenonaphthalenone dyes.

Original languageEnglish
Pages (from-to)995-1004
Number of pages10
JournalDyes and Pigments
Volume92
Issue number3
DOIs
Publication statusPublished - 1 Mar 2012
Externally publishedYes

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Photochromism
Bearings (structural)
Dyes
Positive ions
Cations
Irradiation
Color
Catalysts
Acids
Coloring Agents
2H-naphtho(1,2-b)pyran
merocyanine dye

Cite this

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title = "The intramolecular capture of thermally generated merocyanine dyes derived from naphthopyrans: Photochromism of 5-(diarylhydroxymethyl)-2H-naphtho[1,2-b] pyrans",
abstract = "A series of 2H-naphtho[1,2-b]pyrans bearing a diarylmethanol unit at C-5 have been synthesised by the addition of an excess of an aryllithium reagent to alkyl 2H-naphtho[1,2-b]pyran-5-carboxylate precursors. These naphthopyrans show photochromism when exposed to ultraviolet irradiation and also generate intense colours at low pH through triarylmethine cation generation. However, photochromism of the triarylmethine cation derived from the naphthopyran unit could not be detected. An irreversible cascade process initiated by the thermally-induced ring-opening of the diarylmethanol substituted 2H-naphtho[1,2-b]pyrans in the presence of an acid catalyst afforded novel benzopentalenonaphthalenone dyes.",
keywords = "Absorption, Benzo[5,6]pentaleno[1,2-b]naphthalene, Naphthopyran, Photochromism, Synthesis, Triarylmethine cationic dye",
author = "Gabbutt, {Christopher D.} and Gibbons, {Lucy V.} and Heron, {B. Mark} and Kolla, {Suresh B.}",
year = "2012",
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doi = "10.1016/j.dyepig.2011.07.004",
language = "English",
volume = "92",
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journal = "Dyes and Pigments",
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TY - JOUR

T1 - The intramolecular capture of thermally generated merocyanine dyes derived from naphthopyrans

T2 - Photochromism of 5-(diarylhydroxymethyl)-2H-naphtho[1,2-b] pyrans

AU - Gabbutt, Christopher D.

AU - Gibbons, Lucy V.

AU - Heron, B. Mark

AU - Kolla, Suresh B.

PY - 2012/3/1

Y1 - 2012/3/1

N2 - A series of 2H-naphtho[1,2-b]pyrans bearing a diarylmethanol unit at C-5 have been synthesised by the addition of an excess of an aryllithium reagent to alkyl 2H-naphtho[1,2-b]pyran-5-carboxylate precursors. These naphthopyrans show photochromism when exposed to ultraviolet irradiation and also generate intense colours at low pH through triarylmethine cation generation. However, photochromism of the triarylmethine cation derived from the naphthopyran unit could not be detected. An irreversible cascade process initiated by the thermally-induced ring-opening of the diarylmethanol substituted 2H-naphtho[1,2-b]pyrans in the presence of an acid catalyst afforded novel benzopentalenonaphthalenone dyes.

AB - A series of 2H-naphtho[1,2-b]pyrans bearing a diarylmethanol unit at C-5 have been synthesised by the addition of an excess of an aryllithium reagent to alkyl 2H-naphtho[1,2-b]pyran-5-carboxylate precursors. These naphthopyrans show photochromism when exposed to ultraviolet irradiation and also generate intense colours at low pH through triarylmethine cation generation. However, photochromism of the triarylmethine cation derived from the naphthopyran unit could not be detected. An irreversible cascade process initiated by the thermally-induced ring-opening of the diarylmethanol substituted 2H-naphtho[1,2-b]pyrans in the presence of an acid catalyst afforded novel benzopentalenonaphthalenone dyes.

KW - Absorption

KW - Benzo[5,6]pentaleno[1,2-b]naphthalene

KW - Naphthopyran

KW - Photochromism

KW - Synthesis

KW - Triarylmethine cationic dye

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U2 - 10.1016/j.dyepig.2011.07.004

DO - 10.1016/j.dyepig.2011.07.004

M3 - Article

VL - 92

SP - 995

EP - 1004

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

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ER -