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Synthesis of Meso-Substituted Subphthalocyanine-Subporphyrin Hybrids: Boron Subtribenzodiazaporphyrins

Synthesis of Meso-Substituted Subphthalocyanine-Subporphyrin Hybrids: Boron Subtribenzodiazaporphyrins
Synthesis of Meso-Substituted Subphthalocyanine-Subporphyrin Hybrids: Boron Subtribenzodiazaporphyrins

The first syntheses of hybrid structures that lie between subphthalocyanines and subporphyrins are reported. The versatile single-step synthetic method uses a preformed aminoisoindolene to provide the bridging methine unit and its substituent while trialkoxyborates simultaneously act as Lewis acid, template, and provider of the apical substituent. The selection of each component therefore allows for the controlled formation of diverse, differentially functionalized systems. The new hybrids are isolated as robust, pure materials that display intense absorption and emission in the mid-visible region. The new compounds are further characterized in solution and solid state by variable-temperature NMR spectroscopy and X-ray crystallography, respectively.

dyes/pigments, heterocycles, phthalocyanines, porphyrinoids, synthetic methods
1433-7851
7510-7514
Remiro-Buenamañana, Sonia
9176f285-75ea-4567-846c-2a7ed6364b5d
Díaz-Moscoso, Alejandro
0add82f3-aaff-4875-b2d8-e25e29e7d59e
Hughes, David L.
d3b8245e-976a-47e6-8fe6-6ebcf38e2255
Bochmann, Manfred
ec2bb201-23cc-4f91-aa80-258e6c8cc9fb
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Cammidge, Andrew N.
e7a6b5be-5613-416e-8f1a-40b4744ecf65
Remiro-Buenamañana, Sonia
9176f285-75ea-4567-846c-2a7ed6364b5d
Díaz-Moscoso, Alejandro
0add82f3-aaff-4875-b2d8-e25e29e7d59e
Hughes, David L.
d3b8245e-976a-47e6-8fe6-6ebcf38e2255
Bochmann, Manfred
ec2bb201-23cc-4f91-aa80-258e6c8cc9fb
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Cammidge, Andrew N.
e7a6b5be-5613-416e-8f1a-40b4744ecf65

Remiro-Buenamañana, Sonia, Díaz-Moscoso, Alejandro, Hughes, David L., Bochmann, Manfred, Tizzard, Graham J., Coles, Simon J. and Cammidge, Andrew N. (2015) Synthesis of Meso-Substituted Subphthalocyanine-Subporphyrin Hybrids: Boron Subtribenzodiazaporphyrins. Angewandte Chemie - International Edition, 54 (26), 7510-7514. (doi:10.1002/anie.201502662).

Record type: Article

Abstract

The first syntheses of hybrid structures that lie between subphthalocyanines and subporphyrins are reported. The versatile single-step synthetic method uses a preformed aminoisoindolene to provide the bridging methine unit and its substituent while trialkoxyborates simultaneously act as Lewis acid, template, and provider of the apical substituent. The selection of each component therefore allows for the controlled formation of diverse, differentially functionalized systems. The new hybrids are isolated as robust, pure materials that display intense absorption and emission in the mid-visible region. The new compounds are further characterized in solution and solid state by variable-temperature NMR spectroscopy and X-ray crystallography, respectively.

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More information

e-pub ahead of print date: 15 May 2015
Published date: 17 June 2015
Keywords: dyes/pigments, heterocycles, phthalocyanines, porphyrinoids, synthetic methods

Identifiers

Local EPrints ID: 446654
URI: http://eprints.soton.ac.uk/id/eprint/446654
ISSN: 1433-7851
PURE UUID: d48a91bf-9fe3-4e7f-8f57-09596e443432
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: 17 Feb 2021 17:31
Last modified: 20 Feb 2021 02:37

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Contributors

Author: Sonia Remiro-Buenamañana
Author: Alejandro Díaz-Moscoso
Author: David L. Hughes
Author: Manfred Bochmann
Author: Simon J. Coles ORCID iD
Author: Andrew N. Cammidge

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