Expanded porphyrin-like structures based on twinned triphenylenes

Hemant Gopee; Xiangfei Kong; Zhiqun He; Isabelle Chambrier; David L. Hughes; Graham J. Tizzard; Simon J. Coles; Andrew N. Cammidge

doi:10.1021/jo401551c

Expanded porphyrin-like structures based on twinned triphenylenes

Hemant Gopee, Xiangfei Kong, Zhiqun He, Isabelle Chambrier, David L. Hughes, Graham J. Tizzard, Simon J. Coles, Andrew N. Cammidge

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

30 Citations (Scopus)

Abstract

Triphenylene twins are intriguing structures, and those bridged through their 3,6-positions by dipyrromethene units give a new class of macrocycles that can be viewed as rigid, expanded porphyrin derivatives in which coplanarity is enforced in a formally antiaromatic π system. Somewhat surprisingly, however, macrocyclization leads to significant overall stabilization of the dipyrromethene chromophores.

Original language	English
Pages (from-to)	9505-9511
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	78
Issue number	18
DOIs	https://doi.org/10.1021/jo401551c
Publication status	Published - 20 Sept 2013

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10.1021/jo401551c

Cite this

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title = "Expanded porphyrin-like structures based on twinned triphenylenes",

abstract = "Triphenylene twins are intriguing structures, and those bridged through their 3,6-positions by dipyrromethene units give a new class of macrocycles that can be viewed as rigid, expanded porphyrin derivatives in which coplanarity is enforced in a formally antiaromatic π system. Somewhat surprisingly, however, macrocyclization leads to significant overall stabilization of the dipyrromethene chromophores.",

author = "Hemant Gopee and Xiangfei Kong and Zhiqun He and Isabelle Chambrier and Hughes, {David L.} and Tizzard, {Graham J.} and Coles, {Simon J.} and Cammidge, {Andrew N.}",

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T1 - Expanded porphyrin-like structures based on twinned triphenylenes

AU - Gopee, Hemant

AU - Kong, Xiangfei

AU - He, Zhiqun

AU - Chambrier, Isabelle

AU - Hughes, David L.

AU - Tizzard, Graham J.

AU - Coles, Simon J.

AU - Cammidge, Andrew N.

PY - 2013/9/20

Y1 - 2013/9/20

N2 - Triphenylene twins are intriguing structures, and those bridged through their 3,6-positions by dipyrromethene units give a new class of macrocycles that can be viewed as rigid, expanded porphyrin derivatives in which coplanarity is enforced in a formally antiaromatic π system. Somewhat surprisingly, however, macrocyclization leads to significant overall stabilization of the dipyrromethene chromophores.

AB - Triphenylene twins are intriguing structures, and those bridged through their 3,6-positions by dipyrromethene units give a new class of macrocycles that can be viewed as rigid, expanded porphyrin derivatives in which coplanarity is enforced in a formally antiaromatic π system. Somewhat surprisingly, however, macrocyclization leads to significant overall stabilization of the dipyrromethene chromophores.

U2 - 10.1021/jo401551c

DO - 10.1021/jo401551c

M3 - Article

SN - 0022-3263

VL - 78

SP - 9505

EP - 9511

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 18

ER -