A panchromatic supramolecular fullerene-based donor-acceptor assembly derived from a peripherally substituted bodipy-zinc phthalocyanine dyad

Rio Y, Seitz W, Gouloumis A, Vazquez P, Sessler JL, Guldi DM, Torres T (2010)

Publication Type: Journal article, Original article

Publication year: 2010

Journal

Chemistry - A European Journal Wiley-VCH Verlag

Original Authors: Rio Y., Seitz W., Gouloumis A., Vazquez P., Sessler J.L., Guldi D.M., Tomas T.

Publisher: Wiley-VCH Verlag

Book Volume: 16

Pages Range: 1929-1940

Journal Issue: 6

DOI: 10.1002/chem.200902507

Abstract

A panchromatic 4,4-difluoro4-bora-3a,4a-diaza-s-indacene -zinc phthalocyanine conjugate (BodipyZnPc) 1 was synthesized starting from phthalocyanine aldehyde 4, via dipyrromethane 3 and dipyrromethene 2. Conjugate 1 represents the first example in which a Bodipy unit is tethered to the peripheral position of a phthalocyanine core. Electrochemical and optical measurements provided evidence for strong electronic interactions between the Bodipy and ZnPc constituents in the ground state of 1. When conjugate 1 is subjected to photoexcitation in the spectral region corresponding to the Bodipy absorption, the strong fluorescence characteristic of the latter subunit is effectively quenched (i.e., ≥97%). Excitation spectral analysis confirmed that the photoexcited Bodipy and the tethered ZnPc subunits interact and that intraconjugate singlet energy transfer occurs with an efficiency of ca. 25 %. Treatment of conjugate 1 with N-pyridylfulleropyrrolidine (8), an electron-acceptor system containing a nitrogen ligand, gives rise to the novel electron donor-acceptor hybrid l↔8 through ligation to the ZnPc center. Irradiation of the resulting supramolecular ensemble within the visible range leads to a charge-separated Bodipy-ZnPc-C radical-ion-pair state, through a sequence of excited-state and charge transfers, characterized by a remarkably long lifetime of 39.9 ns in toluene. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

Authors with CRIS profile

Dirk Michael Guldi Lehrstuhl für Physikalische Chemie I

Involved external institutions

Universidad Autónoma de Madrid (UAM) ES Spain (ES) University of Texas at Austin US United States (USA) (US)

How to cite

APA:

Rio, Y., Seitz, W., Gouloumis, A., Vazquez, P., Sessler, J.L., Guldi, D.M., & Torres, T. (2010). A panchromatic supramolecular fullerene-based donor-acceptor assembly derived from a peripherally substituted bodipy-zinc phthalocyanine dyad. Chemistry - A European Journal, 16(6), 1929-1940. https://dx.doi.org/10.1002/chem.200902507

MLA:

Rio, Yannick, et al. "A panchromatic supramolecular fullerene-based donor-acceptor assembly derived from a peripherally substituted bodipy-zinc phthalocyanine dyad." Chemistry - A European Journal 16.6 (2010): 1929-1940.

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