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Improved syntheses of meso-aryl tetrabenzotriazaporphyrins (TBTAPs)

Improved syntheses of meso-aryl tetrabenzotriazaporphyrins (TBTAPs)
Improved syntheses of meso-aryl tetrabenzotriazaporphyrins (TBTAPs)
New tetrabenzotriazaporphyrins are reported that are functionalised at the meso-position. The derivatives functionalised with meso-bromophenyl substituents are synthesised using an improved variation on the traditional reaction between phthalonitriles and Grignard reagents. For all other new derivatives, a modern protocol is employed that gives convenient access to these challenging materials by template co-macrocyclisation between phthalonitriles and aryl-aminoisoindoline derivatives like 15. The newly developed procedure allows design and synthesis of elaborate, functional composites and this is demonstrated by synthesis of meso-pyrenylTBTAP 24, a linked double chromophore in which the two complementary units lie perpendicular to each other and therefore have minimal ground state interaction
0040-4020
7370-7379
Alharbi, Nuha
0eae925d-df49-4a5a-8c56-e6e30013c91a
Díaz-Moscoso, Alejandro
0add82f3-aaff-4875-b2d8-e25e29e7d59e
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Cook, Michael J.
9b30e5b0-b828-46a7-a1f6-cd758c3c6c74
Cammidge, Andrew N.
e7a6b5be-5613-416e-8f1a-40b4744ecf65
Alharbi, Nuha
0eae925d-df49-4a5a-8c56-e6e30013c91a
Díaz-Moscoso, Alejandro
0add82f3-aaff-4875-b2d8-e25e29e7d59e
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Cook, Michael J.
9b30e5b0-b828-46a7-a1f6-cd758c3c6c74
Cammidge, Andrew N.
e7a6b5be-5613-416e-8f1a-40b4744ecf65

Alharbi, Nuha, Díaz-Moscoso, Alejandro, Tizzard, Graham J., Coles, Simon J., Cook, Michael J. and Cammidge, Andrew N. (2014) Improved syntheses of meso-aryl tetrabenzotriazaporphyrins (TBTAPs). Tetrahedron, 70 (40), 7370-7379. (doi:10.1016/j.tet.2014.06.086).

Record type: Article

Abstract

New tetrabenzotriazaporphyrins are reported that are functionalised at the meso-position. The derivatives functionalised with meso-bromophenyl substituents are synthesised using an improved variation on the traditional reaction between phthalonitriles and Grignard reagents. For all other new derivatives, a modern protocol is employed that gives convenient access to these challenging materials by template co-macrocyclisation between phthalonitriles and aryl-aminoisoindoline derivatives like 15. The newly developed procedure allows design and synthesis of elaborate, functional composites and this is demonstrated by synthesis of meso-pyrenylTBTAP 24, a linked double chromophore in which the two complementary units lie perpendicular to each other and therefore have minimal ground state interaction

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Published date: 7 October 2014
Organisations: Chemistry

Identifiers

Local EPrints ID: 371990
URI: http://eprints.soton.ac.uk/id/eprint/371990
ISSN: 0040-4020
PURE UUID: 833023e9-2e0b-42f2-9792-ae7efc67f080
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: 24 Nov 2014 11:34
Last modified: 18 Feb 2021 16:57

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Contributors

Author: Nuha Alharbi
Author: Alejandro Díaz-Moscoso
Author: Simon J. Coles ORCID iD
Author: Michael J. Cook
Author: Andrew N. Cammidge

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