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

Synthetic and Medicinal Chemistry

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

32 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

Access to Document

10.1021/jo401551c

Cite this

@article{b06b84bd6f194321874af8cbe57644f3,

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.\}",

year = "2013",

month = sep,

day = "20",

doi = "10.1021/jo401551c",

language = "English",

volume = "78",

pages = "9505--9511",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "18",

}

TY - JOUR

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 -