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

The Journal of Physical Chemistry. B
Mihaela Carmen BalabanTeodor Silviu Balaban

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.

References

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Citations

Mar 4, 2009·Chemical Reviews·Charles Michael DrainIvana Radivojevic
Dec 17, 2008·Chemical Communications : Chem Comm·Fiorella L Callari, Salvatore Sortino
Sep 30, 2015·Organic & Biomolecular Chemistry·Chihiro MaedaNaoki Yoshioka
Oct 7, 2016·Chemical Reviews·Satoru HirotoHiroshi Shinokubo
Apr 24, 2012·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Aldo JesorkaTeodor Silviu Balaban
Feb 15, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kento UetaAtsuhiro Osuka
Feb 2, 2021·European Journal of Organic Chemistry·Harry C Sample, Mathias O Senge
Jan 8, 2011·The Journal of Physical Chemistry. a·Pippara Hemant KumarPrakriti Ranjan Bangal
Mar 26, 2013·Journal of the American Chemical Society·Yoshinao ShinozakiJoe Otsuki

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