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

doi:10.1080/15421400590946334

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 journal › Article › peer-review

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 λ_max of the photomerocyanine from a 2H,9H-indeno[1,2-f]naphtho[2,1-b]pyran is presented.

Original language	English
Pages (from-to)	167-172
Number of pages	6
Journal	Molecular Crystals and Liquid Crystals
Volume	430
Issue number	1
DOIs	https://doi.org/10.1080/15421400590946334
Publication status	Published - 1 Dec 2005
Externally published	Yes

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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",

author = "Gabbutt, \{Christopher D.\} and Heron, \{B. Mark\} and Mars, \{Craig A.\} and Partington, \{Steven M.\}",

year = "2005",

month = dec,

day = "1",

doi = "10.1080/15421400590946334",

language = "English",

volume = "430",

pages = "167--172",

journal = "Molecular Crystals and Liquid Crystals",

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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

UR - https://www.scopus.com/pages/publications/33644749304

U2 - 10.1080/15421400590946334

DO - 10.1080/15421400590946334

M3 - Article

AN - SCOPUS:33644749304

SN - 1542-1406

VL - 430

SP - 167

EP - 172

JO - Molecular Crystals and Liquid Crystals

JF - Molecular Crystals and Liquid Crystals

IS - 1

ER -

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

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