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Expanded porphyrin-like structures based on twinned triphenylenes

Expanded porphyrin-like structures based on twinned triphenylenes
Expanded porphyrin-like structures based on twinned triphenylenes
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 pi system. Somewhat surprisingly, however, macrocyclization leads to significant overall stabilization of the dipyrromethene chromophores.
0022-3263
9505-9511
Gopee, Hemant
afac69bb-7b26-453c-aa7a-9962e5205405
Kong, Xiangfei
c7395270-34e2-4764-bebd-77837cb3a2fe
He, Zhiqun
67e983b2-22ca-40a2-b7fb-1a44fe9d6017
Chambrier, Isabelle
d3ad81b8-12d1-4f7a-bc04-99da7f4c0d50
Hughes, David L.
d3b8245e-976a-47e6-8fe6-6ebcf38e2255
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Cammidge, Andrew N.
e7a6b5be-5613-416e-8f1a-40b4744ecf65
Gopee, Hemant
afac69bb-7b26-453c-aa7a-9962e5205405
Kong, Xiangfei
c7395270-34e2-4764-bebd-77837cb3a2fe
He, Zhiqun
67e983b2-22ca-40a2-b7fb-1a44fe9d6017
Chambrier, Isabelle
d3ad81b8-12d1-4f7a-bc04-99da7f4c0d50
Hughes, David L.
d3b8245e-976a-47e6-8fe6-6ebcf38e2255
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Cammidge, Andrew N.
e7a6b5be-5613-416e-8f1a-40b4744ecf65

Gopee, Hemant, Kong, Xiangfei, He, Zhiqun, Chambrier, Isabelle, Hughes, David L., Tizzard, Graham J., Coles, Simon J. and Cammidge, Andrew N. (2013) Expanded porphyrin-like structures based on twinned triphenylenes. Journal of Organic Chemistry, 78 (18), 9505-9511. (doi:10.1021/jo401551c).

Record type: Article

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 pi system. Somewhat surprisingly, however, macrocyclization leads to significant overall stabilization of the dipyrromethene chromophores.

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More information

e-pub ahead of print date: 29 August 2013
Published date: 11 September 2013
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry

Identifiers

Local EPrints ID: 362487
URI: http://eprints.soton.ac.uk/id/eprint/362487
ISSN: 0022-3263
PURE UUID: 1477385c-71f8-4b06-ac6b-60130c7e8364
ORCID for Graham J. Tizzard: ORCID iD orcid.org/0000-0002-1577-5779
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 25 Feb 2014 14:03
Last modified: 18 Feb 2021 16:57

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Contributors

Author: Hemant Gopee
Author: Xiangfei Kong
Author: Zhiqun He
Author: Isabelle Chambrier
Author: David L. Hughes
Author: Simon J. Coles ORCID iD
Author: Andrew N. Cammidge

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