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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.
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 π-stacking and a CNZn 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.
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- Category:
- Articles
- Type:
- artykuł w czasopiśmie wyróżnionym w JCR
- Published in:
-
JOURNAL OF PHYSICAL CHEMISTRY B
no. 112,
pages 5512 - 5521,
ISSN: 1520-6106 - Language:
- English
- Publication year:
- 2008
- Bibliographic description:
- Balaban M. C., Eichhöfer A., Buth G., Hauschild R., Szmytkowski J., Kalt H., Balaban T. S.: 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.// JOURNAL OF PHYSICAL CHEMISTRY B. -Vol. 112, iss. 17 (2008), s.5512-5521
- Sources of funding:
-
- COST_FREE
- Verified by:
- Gdańsk University of Technology
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