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 -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.
| Author: | M.C. Balaban, A. Eichhöfer, G. Buth, R. Hauschild, J. Szmytkowski, H. Kalt, T.S. Balaban |
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| Source: | J. Phys. Chem. B, 112 (17), 5512 -5521, 2008 |
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