Improved syntheses of meso-aryl tetrabenzotriazaporphyrins (TBTAPs)

Alharbi, Nuha, Diaz-Moscoso, Alejandro, Tizzard, Graham J., Coles, Simon J., Cook, Michael J. and Cammidge, Andrew N. ORCID: (2014) Improved syntheses of meso-aryl tetrabenzotriazaporphyrins (TBTAPs). Tetrahedron, 70 (40). pp. 7370-7379. ISSN 0040-4020

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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.

Item Type: Article
Uncontrolled Keywords: phthalocyanines,porphyrins,heterocycles,synthesis,hybrids,pyrene
Faculty \ School: Faculty of Science > School of Chemistry
Depositing User: Pure Connector
Date Deposited: 16 Dec 2014 13:54
Last Modified: 12 May 2023 09:31
DOI: 10.1016/j.tet.2014.06.086

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