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DABCO-Directed Self-Assembly of Bisporphyrins (DABCO=1,4-Diazabicyclo[2.2.2]octane)

✍ Scribed by Pablo Ballester; Antoni Costa; Ana M. Castilla; Pere M. Deyà; Antonio Frontera; Rosa M. Gomila; Christopher A. Hunter

Publisher: John Wiley and Sons
Year: 2005
Tongue: English
Weight: 239 KB
Volume: 11
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.200400772

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✦ Synopsis

Abstract

Three isomeric zinc bisporphyrins have been prepared by covalently linking together two aminoporphyrins with an isophthalic acid derivative. The porphyrins differ in the substitution pattern on the meso phenyl groups, that is, ortho, meta, or para. Titrations carried out by UV‐visible and ^1^H NMR spectroscopy have been used to map out the stabilities and the stoichiometries of the complexes formed with 1,4‐diazabicyclo[2.2.2]octane (DABCO) in chloroform. The ortho‐ and __meta‐__substituted bisporphyrins form 1:1 intramolecular sandwich complexes. The __para‐__substituted bisporphyrin cannot adopt the cofacial conformation required for this type of complex and forms a higher order 2:2 intermolecular assembly, which is stable over a wide range of DABCO concentrations.

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