Distorted fused porphyrin-phthalocyanine conjugates: Synthesis and photophysics of supramolecular assembled systems with a pyridylfullerene

Pereira AMVM, Soares ARM, Hausmann A, Neves MGPMS, Tome AC, Silva AMS, Cavaleiro JAS, Guldi DM, Torres T (2011)

Publication Type: Journal article, Original article

Publication year: 2011

Journal

Physical Chemistry Chemical Physics Royal Society of Chemistry

Original Authors: Pereira A.M.V.M., Soares A.R.M., Hausmann A., Neves M.G.P.M.S., Tome A.C., Silva A.M.S., Cavaleiro J.A.S., Guldi D.M., Torres T.

Publisher: Royal Society of Chemistry

Book Volume: 13

Pages Range: 11858-11863

Journal Issue: 25

DOI: 10.1039/c1cp00016k

Abstract

In the current work, we report on the synthesis and photophysical features of supramolecular hybrid systems that are based on newly fused porphyrin-phthalocyanine (P-Pc) conjugates and a pyridylfullerene. The ZnP-ZnPc conjugate was synthesized in three steps starting with a Diels-Alder reaction between β-vinylporphyrin and fumaronitrile. The resulting mixture of isomeric adducts was then dehydrogenated to yield the corresponding benzo[b]porphyrin-2,2-dicarbonitrile. In the final step, cyclotetramerization with 4-tert-butylphthalonitrile, in the presence of zinc acetate, afforded the bis-metalated conjugate. Selective demetallation of ZnP led to the HP-ZnPc conjugate. For both conjugates steric hindrance is the inception to a bent configuration, which does, however, not preclude enlargement of the π-conjugated system, that is, the porphyrins and the phthalocyanines. The two conjugates coordinate N-(4-pyridyl)fullero[c] pyrrolidine giving rise to the corresponding supramolecular porphyrin- phthalocyanine-fullerene systems. Photophysical measurements corroborate a sequential deactivation in the excited state, namely an initial intramolecular energy transfer from ZnP or HP to ZnPc followed by an intramolecular charge transfer to yield ZnP-(ZnPc)-(C) and HP-(ZnPc)-(C), respectively. © the Owner Societies 2011.

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) ES Spain (ES) University of Aveiro / Universidade de Aveiro PT Portugal (PT)

How to cite

APA:

Pereira, A.M.V.M., Soares, A.R.M., Hausmann, A., Neves, M.G.P.M.S., Tome, A.C., Silva, A.M.S.,... Torres, T. (2011). Distorted fused porphyrin-phthalocyanine conjugates: Synthesis and photophysics of supramolecular assembled systems with a pyridylfullerene. Physical Chemistry Chemical Physics, 13(25), 11858-11863. https://dx.doi.org/10.1039/c1cp00016k

MLA:

Pereira, Ana M. V. M., et al. "Distorted fused porphyrin-phthalocyanine conjugates: Synthesis and photophysics of supramolecular assembled systems with a pyridylfullerene." Physical Chemistry Chemical Physics 13.25 (2011): 11858-11863.

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