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Complementary syntheses giving access to a full suite of differentially substituted phthalocyanine‐porphyrin hybrids

Complementary syntheses giving access to a full suite of differentially substituted phthalocyanine‐porphyrin hybrids
Complementary syntheses giving access to a full suite of differentially substituted phthalocyanine‐porphyrin hybrids
Phthalocyanines and porphyrins are often the scaffolds of choice for use in widespread applications. Synthetic advances allow bespoke derivatives to be made, tailoring their properties. The selective synthesis of unsymmetrical systems, particularly phthalocyanines, has remained a significant unmet challenge. Porphyrin‐phthalocyanine hybrids offer the potential to combine the favorable features of both parent structures, but again synthetic strategies are poorly developed. Here we demonstrate strategies that give straightforward, controlled access to differentially substituted meso‐aryl‐tetrabenzotriazaporphyrins by reaction between an aryl‐aminoisoindolene ( A ) initiator and a complementary phthalonitrile ( B ). The choice of precursors and reaction conditions allows selective preparation of 1:3 Ar‐ABBB and, uniquely, 2:2 Ar‐ABBA functionalised hybrids.
phthalocyanines, porphyrinoids, hybrids, synthesis, selectivity
1433-7851
Cammidge, Andrew N.
e7a6b5be-5613-416e-8f1a-40b4744ecf65
Alkorbi, Faeza
637d04b2-03c9-4fd9-9015-a1d0e45ebb43
Díaz-Moscoso, Alejandro
0add82f3-aaff-4875-b2d8-e25e29e7d59e
Gretton, Jacob
0be4e5ca-e1b6-4886-99cb-8a6648de38a6
Chambrier, Isabelle
d3ad81b8-12d1-4f7a-bc04-99da7f4c0d50
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hughes, David L.
d3b8245e-976a-47e6-8fe6-6ebcf38e2255
Cammidge, Andrew N.
e7a6b5be-5613-416e-8f1a-40b4744ecf65
Alkorbi, Faeza
637d04b2-03c9-4fd9-9015-a1d0e45ebb43
Díaz-Moscoso, Alejandro
0add82f3-aaff-4875-b2d8-e25e29e7d59e
Gretton, Jacob
0be4e5ca-e1b6-4886-99cb-8a6648de38a6
Chambrier, Isabelle
d3ad81b8-12d1-4f7a-bc04-99da7f4c0d50
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hughes, David L.
d3b8245e-976a-47e6-8fe6-6ebcf38e2255

Cammidge, Andrew N., Alkorbi, Faeza, Díaz-Moscoso, Alejandro, Gretton, Jacob, Chambrier, Isabelle, Tizzard, Graham J., Coles, Simon J. and Hughes, David L. (2021) Complementary syntheses giving access to a full suite of differentially substituted phthalocyanine‐porphyrin hybrids. Angewandte Chemie International Edition. (doi:10.1002/anie.202016596).

Record type: Article

Abstract

Phthalocyanines and porphyrins are often the scaffolds of choice for use in widespread applications. Synthetic advances allow bespoke derivatives to be made, tailoring their properties. The selective synthesis of unsymmetrical systems, particularly phthalocyanines, has remained a significant unmet challenge. Porphyrin‐phthalocyanine hybrids offer the potential to combine the favorable features of both parent structures, but again synthetic strategies are poorly developed. Here we demonstrate strategies that give straightforward, controlled access to differentially substituted meso‐aryl‐tetrabenzotriazaporphyrins by reaction between an aryl‐aminoisoindolene ( A ) initiator and a complementary phthalonitrile ( B ). The choice of precursors and reaction conditions allows selective preparation of 1:3 Ar‐ABBB and, uniquely, 2:2 Ar‐ABBA functionalised hybrids.

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More information

Accepted/In Press date: 7 January 2021
e-pub ahead of print date: 11 January 2021
Keywords: phthalocyanines, porphyrinoids, hybrids, synthesis, selectivity

Identifiers

Local EPrints ID: 447012
URI: http://eprints.soton.ac.uk/id/eprint/447012
ISSN: 1433-7851
PURE UUID: 0b02917f-2b66-484f-98d3-2846369d56cf
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

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Date deposited: 01 Mar 2021 17:34
Last modified: 02 Mar 2021 02:36

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Contributors

Author: Andrew N. Cammidge
Author: Faeza Alkorbi
Author: Alejandro Díaz-Moscoso
Author: Jacob Gretton
Author: Isabelle Chambrier
Author: Simon J. Coles ORCID iD
Author: David L. Hughes

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