Enhancing molecular recognition in electron donor-acceptor hybrids via cooperativity

Krick Calderon R, Valero J, Grimm B, De Mendoza J, Guldi DM (2014)

Publication Type: Journal article

Publication year: 2014

Journal

Journal of the American Chemical Society American Chemical Society

Book Volume: 136

Pages Range: 11436-11443

Journal Issue: 32

DOI: 10.1021/ja5052236

Abstract

Herein, we report the synthesis of guanidinium bis-porphyrin tweezers 1 and fullerene carboxylate 3, their assembly into a novel supramolecular 1@3 electron donor-acceptor hybrid, and its characterization. In solution, the binding constant affording 1@3 is exceptionally high. 1@3, which features a highly confined topography, builds up from a combination of guanidinium- carboxylate hydrogen bonding and π-π stacking/charge-transfer motifs. The latter is governed by interactions between the electron-donating porphyrin and the electron-accepting fullerene. Importantly, positive cooperativity between the applied binding motifs is corroborated by a number of experimental techniques, such as NMR, absorption, fluorescence, etc. In addition, transient absorption experiments shed light onto electron-transfer processes taking place in the ground state and upon photoexcitation. In fact, porphyrin excitation powers an electron transfer to the fullerene yielding charge separated state lifetimes in the nanosecond regime. © 2014 American Chemical Society.

Authors with CRIS profile

Rafael Krick Calderon Lehrstuhl für Physikalische Chemie I Bruno Grimm Graduiertenzentrum der FAU Dirk Michael Guldi Lehrstuhl für Physikalische Chemie I

Involved external institutions

Institute of Chemical Research of Catalonia / Institut Català d'Investigació Química (ICIQ) ES Spain (ES)

How to cite

APA:

Krick Calderon, R., Valero, J., Grimm, B., De Mendoza, J., & Guldi, D.M. (2014). Enhancing molecular recognition in electron donor-acceptor hybrids via cooperativity. Journal of the American Chemical Society, 136(32), 11436-11443. https://doi.org/10.1021/ja5052236

MLA:

Krick Calderon, Rafael, et al. "Enhancing molecular recognition in electron donor-acceptor hybrids via cooperativity." Journal of the American Chemical Society 136.32 (2014): 11436-11443.

BibTeX: Download