Synthesis and photophysical properties of fullerene-phthalocyanine- porphyrin triads and pentads
Enes RF, Cid JJ, Hausmann A, Trukhina O, Gouloumis A, Vazquez P, Cavaleiro JAS, Tome AC, Guldi DM, Torres T (2012)
Publication Type: Journal article, Original article
Publication year: 2012
Journal
Original Authors: Enes R.F., Cid J.-J., Hausmann A., Trukhina O., Gouloumis A., Vazquez P., Cavaleiro J.A.S., Tome A.C., Guldi D.M., Torres T.
Publisher: Wiley-VCH Verlag
Book Volume: 18
Pages Range: 1727-1736
Journal Issue: 6
Abstract
The synthesis and photophysical properties of several fullerene- phthalocyanine-porphyrin triads (1-3) and pentads (4-6) are described. The three photoactive moieties were covalently connected in an one-step synthesis through 1,3-dipolar cycloaddition to C of the corresponding azomethine ylides generated in situ by condensation reaction of a substituted N-porphyrinylmethylglycine derivative and an appropriated formyl phthalocyanine or a diformyl phthalocyanine derivative, respectively. ZnP-C -ZnPc (3), (ZnP) -ZnPc-(C ) (6), and (H P) -ZnPc-(C ) (5) give rise upon excitation of their ZnP or H P components to a sequence of energy and charge-transfer reactions with, however, fundamentally different outcomes. With (ZnP) -ZnPc-(C ) (6) the major pathway is an highly exothermic charge transfer to afford (ZnP)(ZnP )-ZnPc- (C )(C ). The lower singlet excited state energy of H P (i.e., ca. 0.2 eV) and likewise its more anodic oxidation (i.e., ca. 0.2 V) renders the direct charge transfer in (H P) -ZnPc-(C ) (5) not competitive. Instead, a transduction of singlet excited state energy prevails to form the ZnPc singlet excited state. This triggers then an intramolecular charge transfer reaction to form exclusively (H P) -ZnPc -(C )(C ). A similar sequence is found for ZnP-C -ZnPc (3). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Authors with CRIS profile
Anita Hausmann
Lehrstuhl für Physikalische Chemie I
Dirk Michael Guldi
Lehrstuhl für Physikalische Chemie I
Involved external institutions
Universidad Autónoma de Madrid (UAM)
Spain (ES)
University of Aveiro / Universidade de Aveiro
Portugal (PT)
Universidad Complutense de Madrid (UCM)
Spain (ES)
Spain (ES)
University of Aveiro / Universidade de Aveiro
Portugal (PT)
Universidad Complutense de Madrid (UCM)
Spain (ES)
How to cite
APA:
Enes, R.F., Cid, J.-J., Hausmann, A., Trukhina, O., Gouloumis, A., Vazquez, P.,... Torres, T. (2012). Synthesis and photophysical properties of fullerene-phthalocyanine- porphyrin triads and pentads. Chemistry - A European Journal, 18(6), 1727-1736. https://doi.org/10.1002/chem.201102819
MLA:
Enes, Roger F., et al. "Synthesis and photophysical properties of fullerene-phthalocyanine- porphyrin triads and pentads." Chemistry - A European Journal 18.6 (2012): 1727-1736.
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