5-Hydroxy substituted naphthofurans and naphthothiazoles as precursors of photochromic benzochromenes

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Abstract

3-Benzoylnaphtho[1,2-b]furan-5-ol forms a photochromic benzochromene upon reaction with a 1,1-diarylprop-2-yn-1-ol affording a red coloured photomerocyanine, with a half-life of 2.3 min, upon UV-irradiation. Retention of the initial 1,4-oxygenation pattern of the naphthalene moiety through replacement of the furan unit with a methoxy group led to a benzochromene, which developed a similar red colour upon UV-irradiation but was more persistent with a half-life of over 42 min. Treatment of the 3-benzoylnaphtho[1,2-b]furan-5-ol with a 1,1,3-triarylprop-2-yn-1-ol similarly afforded a benzochromene, which did not display any photochromism at ambient temperature as a consequence of steric interactions in the photomerocyanines. The synthesis of N-(5-hydroxynaphtho[1,2-d]thiazol-2-yl)acetamide, as a precursor to a photochromic hetero-fused benzochromene, by the mild selective deprotection of the O-acetyl group of 2-acetamidonaphtho[1,2-d]thiazol-5-yl acetate was complicated by a facile, competitive, oxidative dimerisation to afford a novel [2,2′-binaphthothiazole]-1,1′-diol.
LanguageEnglish
Pages9352-9358
JournalTetrahedron
Volume70
Issue number49
DOIs
Publication statusPublished - 9 Dec 2014

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Half-Life
Irradiation
Photochromism
Oxygenation
Dimerization
Acetates
Color
Temperature
furan
acetamide
naphthalene

Cite this

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title = "5-Hydroxy substituted naphthofurans and naphthothiazoles as precursors of photochromic benzochromenes",
abstract = "3-Benzoylnaphtho[1,2-b]furan-5-ol forms a photochromic benzochromene upon reaction with a 1,1-diarylprop-2-yn-1-ol affording a red coloured photomerocyanine, with a half-life of 2.3 min, upon UV-irradiation. Retention of the initial 1,4-oxygenation pattern of the naphthalene moiety through replacement of the furan unit with a methoxy group led to a benzochromene, which developed a similar red colour upon UV-irradiation but was more persistent with a half-life of over 42 min. Treatment of the 3-benzoylnaphtho[1,2-b]furan-5-ol with a 1,1,3-triarylprop-2-yn-1-ol similarly afforded a benzochromene, which did not display any photochromism at ambient temperature as a consequence of steric interactions in the photomerocyanines. The synthesis of N-(5-hydroxynaphtho[1,2-d]thiazol-2-yl)acetamide, as a precursor to a photochromic hetero-fused benzochromene, by the mild selective deprotection of the O-acetyl group of 2-acetamidonaphtho[1,2-d]thiazol-5-yl acetate was complicated by a facile, competitive, oxidative dimerisation to afford a novel [2,2′-binaphthothiazole]-1,1′-diol.",
keywords = "Benzochromene, Oxidative dimerisation, Photochromism, Quinone, Synthesis",
author = "Stuart Aiken and Ben Allsopp and Kathryn Booth and Gabbutt, {Christopher D.} and Heron, {B. Mark} and Rice, {Craig R.}",
year = "2014",
month = "12",
day = "9",
doi = "10.1016/j.tet.2014.10.043",
language = "English",
volume = "70",
pages = "9352--9358",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
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5-Hydroxy substituted naphthofurans and naphthothiazoles as precursors of photochromic benzochromenes. / Aiken, Stuart; Allsopp, Ben; Booth, Kathryn; Gabbutt, Christopher D.; Heron, B. Mark; Rice, Craig R.

In: Tetrahedron, Vol. 70, No. 49, 09.12.2014, p. 9352-9358.

Research output: Contribution to journalArticle

TY - JOUR

T1 - 5-Hydroxy substituted naphthofurans and naphthothiazoles as precursors of photochromic benzochromenes

AU - Aiken, Stuart

AU - Allsopp, Ben

AU - Booth, Kathryn

AU - Gabbutt, Christopher D.

AU - Heron, B. Mark

AU - Rice, Craig R.

PY - 2014/12/9

Y1 - 2014/12/9

N2 - 3-Benzoylnaphtho[1,2-b]furan-5-ol forms a photochromic benzochromene upon reaction with a 1,1-diarylprop-2-yn-1-ol affording a red coloured photomerocyanine, with a half-life of 2.3 min, upon UV-irradiation. Retention of the initial 1,4-oxygenation pattern of the naphthalene moiety through replacement of the furan unit with a methoxy group led to a benzochromene, which developed a similar red colour upon UV-irradiation but was more persistent with a half-life of over 42 min. Treatment of the 3-benzoylnaphtho[1,2-b]furan-5-ol with a 1,1,3-triarylprop-2-yn-1-ol similarly afforded a benzochromene, which did not display any photochromism at ambient temperature as a consequence of steric interactions in the photomerocyanines. The synthesis of N-(5-hydroxynaphtho[1,2-d]thiazol-2-yl)acetamide, as a precursor to a photochromic hetero-fused benzochromene, by the mild selective deprotection of the O-acetyl group of 2-acetamidonaphtho[1,2-d]thiazol-5-yl acetate was complicated by a facile, competitive, oxidative dimerisation to afford a novel [2,2′-binaphthothiazole]-1,1′-diol.

AB - 3-Benzoylnaphtho[1,2-b]furan-5-ol forms a photochromic benzochromene upon reaction with a 1,1-diarylprop-2-yn-1-ol affording a red coloured photomerocyanine, with a half-life of 2.3 min, upon UV-irradiation. Retention of the initial 1,4-oxygenation pattern of the naphthalene moiety through replacement of the furan unit with a methoxy group led to a benzochromene, which developed a similar red colour upon UV-irradiation but was more persistent with a half-life of over 42 min. Treatment of the 3-benzoylnaphtho[1,2-b]furan-5-ol with a 1,1,3-triarylprop-2-yn-1-ol similarly afforded a benzochromene, which did not display any photochromism at ambient temperature as a consequence of steric interactions in the photomerocyanines. The synthesis of N-(5-hydroxynaphtho[1,2-d]thiazol-2-yl)acetamide, as a precursor to a photochromic hetero-fused benzochromene, by the mild selective deprotection of the O-acetyl group of 2-acetamidonaphtho[1,2-d]thiazol-5-yl acetate was complicated by a facile, competitive, oxidative dimerisation to afford a novel [2,2′-binaphthothiazole]-1,1′-diol.

KW - Benzochromene

KW - Oxidative dimerisation

KW - Photochromism

KW - Quinone

KW - Synthesis

U2 - 10.1016/j.tet.2014.10.043

DO - 10.1016/j.tet.2014.10.043

M3 - Article

VL - 70

SP - 9352

EP - 9358

JO - Tetrahedron

T2 - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 49

ER -