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J Phys Chem B. 2008 May 1;112(17):5512-21. doi: 10.1021/jp801510b. Epub 2008 Apr 11.

Programmed metalloporphyrins for self-assembly within light-harvesting stacks: (5,15-dicyano-10,20-bis(3,5-di-tert-butylphenyl)porphyrinato)zinc(II) and its push-pull 15-N,N-dialkylamino-5-cyano congeners obtained by a facile direct amination.

Author information

1
Karlsruhe Institute of Technology, Forschungszentrum Karlsruhe, Institute for Nanotechnology, Postfach 3640, D-76021 Karlsruhe, Germany.

Abstract

The title dicyano compound was synthesized via cyanation and it self-assembles in nonpolar solvents giving red-shifted and broad absorption maxima just as the bacteriochlorophylls which are encountered in the light-harvesting organelles of early photosynthetic bacteria. In the crystal, stacks are formed through a hierarchic combination of pi-stacking and a CN-Zn electrostatic interaction. Push-pull 15-N,N-dialkylamino-5-cyano congeners could be obtained in high yields using a solvent- and catalyst-free direct amination of meso-bromoporphyrins. Importantly, the fluorescence of the self-assembled species due to the very orderly manner in which the chromophores are arranged is not entirely quenched and has a surprisingly long lifetime of over 1 ns. This lends hope of using the trapped energy in biomimetic hybrid solar cells.

PMID:
18402489
DOI:
10.1021/jp801510b
[Indexed for MEDLINE]

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