Synthesis and photochromic properties of 2H,9H-indeno[1,2-f]- and 3H,7H-indeno[2,1-i]-naphtho[2,1-b]pyrans

Christopher D. Gabbutt, B. Mark Heron, Craig A. Mars, Steven M. Partington

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Expedient syntheses of the 3-hydroxy- and 6-hydroxy- derivatives of 11H-benzo[a]-fluoren-11-one, obtained via Suzuki-Miyaura couplings are described. Reactions of these phenols with 1,1-diarylprop-2-yn-1-ols give indeno[2,1-i]- and indeno[1,2-f]-naphtho[2,1-b]pyranones respectively. The photochromic properties of these and the reduced derivatives are reported. A rationale for the pronounced hypsochromic shift in λmax of the photomerocyanine from a 2H,9H-indeno[1,2-f]naphtho[2,1-b]pyran is presented.

LanguageEnglish
Pages167-172
Number of pages6
JournalMolecular Crystals and Liquid Crystals
Volume430
Issue number1
DOIs
Publication statusPublished - 1 Dec 2005
Externally publishedYes

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title = "Synthesis and photochromic properties of 2H,9H-indeno[1,2-f]- and 3H,7H-indeno[2,1-i]-naphtho[2,1-b]pyrans",
abstract = "Expedient syntheses of the 3-hydroxy- and 6-hydroxy- derivatives of 11H-benzo[a]-fluoren-11-one, obtained via Suzuki-Miyaura couplings are described. Reactions of these phenols with 1,1-diarylprop-2-yn-1-ols give indeno[2,1-i]- and indeno[1,2-f]-naphtho[2,1-b]pyranones respectively. The photochromic properties of these and the reduced derivatives are reported. A rationale for the pronounced hypsochromic shift in λmax of the photomerocyanine from a 2H,9H-indeno[1,2-f]naphtho[2,1-b]pyran is presented.",
keywords = "Indenonaphthopyran, Naphthopyran, Photomerocyanine, Suzuki coupling",
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year = "2005",
month = "12",
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doi = "10.1080/15421400590946334",
language = "English",
volume = "430",
pages = "167--172",
journal = "Molecular Crystals and Liquid Crystals",
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Synthesis and photochromic properties of 2H,9H-indeno[1,2-f]- and 3H,7H-indeno[2,1-i]-naphtho[2,1-b]pyrans. / Gabbutt, Christopher D.; Heron, B. Mark; Mars, Craig A.; Partington, Steven M.

In: Molecular Crystals and Liquid Crystals, Vol. 430, No. 1, 01.12.2005, p. 167-172.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis and photochromic properties of 2H,9H-indeno[1,2-f]- and 3H,7H-indeno[2,1-i]-naphtho[2,1-b]pyrans

AU - Gabbutt, Christopher D.

AU - Heron, B. Mark

AU - Mars, Craig A.

AU - Partington, Steven M.

PY - 2005/12/1

Y1 - 2005/12/1

N2 - Expedient syntheses of the 3-hydroxy- and 6-hydroxy- derivatives of 11H-benzo[a]-fluoren-11-one, obtained via Suzuki-Miyaura couplings are described. Reactions of these phenols with 1,1-diarylprop-2-yn-1-ols give indeno[2,1-i]- and indeno[1,2-f]-naphtho[2,1-b]pyranones respectively. The photochromic properties of these and the reduced derivatives are reported. A rationale for the pronounced hypsochromic shift in λmax of the photomerocyanine from a 2H,9H-indeno[1,2-f]naphtho[2,1-b]pyran is presented.

AB - Expedient syntheses of the 3-hydroxy- and 6-hydroxy- derivatives of 11H-benzo[a]-fluoren-11-one, obtained via Suzuki-Miyaura couplings are described. Reactions of these phenols with 1,1-diarylprop-2-yn-1-ols give indeno[2,1-i]- and indeno[1,2-f]-naphtho[2,1-b]pyranones respectively. The photochromic properties of these and the reduced derivatives are reported. A rationale for the pronounced hypsochromic shift in λmax of the photomerocyanine from a 2H,9H-indeno[1,2-f]naphtho[2,1-b]pyran is presented.

KW - Indenonaphthopyran

KW - Naphthopyran

KW - Photomerocyanine

KW - Suzuki coupling

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U2 - 10.1080/15421400590946334

DO - 10.1080/15421400590946334

M3 - Article

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EP - 172

JO - Molecular Crystals and Liquid Crystals

T2 - Molecular Crystals and Liquid Crystals

JF - Molecular Crystals and Liquid Crystals

SN - 1542-1406

IS - 1

ER -