title: Probing Supramolecular Interactions between a Crown Ether Appended Zinc Phthalocyanine and an Ammonium Group Appended to a C60Derivative.
abstract: Self-assembly driven by crown ether complexation of zinc phthalocyanines equipped with one 18-crown-6 moiety and fullerenes bearing an ammonium head group afforded a novel donor-acceptor hybrid. In reference experiments, fullerenes containing a Boc-protected amine functionality have been probed. The circumvention of zinc phthalocyanine aggregation is important for the self-assembly, which required the addition of pyridine. From absorption and fluorescence titration assays, which provided sound and unambiguous evidence for mutual interactions between the electron donor and the electron acceptor within the hybrids, association constants in the order of 8.0×105m-1have been derived. The aforementioned is based on 1:1 stoichiometries, which have been independently confirmed by Job's plot measurements. In the excited state, which has been examined by transient absorption experiments, intermolecular charge separation evolves from the photoexcited zinc phthalocyanine to the fullerene subunit and leads to short-lived charge-separated states. Interestingly, photoexcitation of zinc phthalocyanine dimers/aggregates can also be followed by an intermolecular charge separation between vicinal phthalocyanines. These multicomponent supramolecular ensembles have also been shown by in-depth electrospray ionization mass spectrometry (ESI-MS) studies, giving rise to the formation and detection of a variety of non-covalently linked species.
authors.affiliation: Department of Chemistry and Pharmacy, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-, Nürnberg, Egerlandstrasse 3, 91058, Erlangen, Germany), Fax.
authors.forename: Marcus
authors.initials: M
authors.lastname: Lederer
authors.affiliation: Departamento de Química Orgánica, Universidad Autónoma de Madrid, 28049, Madrid, Spain), Fax.|Laboratoire de Chimie des Matériaux Moléculaires, Université de Strasbourg et CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux (ECPM), 25 rue Becquerel, 67087, Strasbourg Cedex 2, France), Fax.
authors.forename: Uwe
authors.initials: U
authors.lastname: Hahn
authors.affiliation: BioOrganic Mass Spectrometry Laboratory (LSMBO), IPHC, Université de Strasbourg, CNRS UMR7178, 25 rue Becquerel, 67087, Strasbourg, France.
authors.forename: Jean-Marc
authors.initials: JM
authors.lastname: Strub
authors.affiliation: BioOrganic Mass Spectrometry Laboratory (LSMBO), IPHC, Université de Strasbourg, CNRS UMR7178, 25 rue Becquerel, 67087, Strasbourg, France.
authors.forename: Sarah
authors.initials: S
authors.lastname: Cianférani
authors.affiliation: BioOrganic Mass Spectrometry Laboratory (LSMBO), IPHC, Université de Strasbourg, CNRS UMR7178, 25 rue Becquerel, 67087, Strasbourg, France.
authors.forename: Alain
authors.initials: A
authors.lastname: Van Dorsselaer
authors.affiliation: Laboratoire de Chimie des Matériaux Moléculaires, Université de Strasbourg et CNRS (UMR 7509), Ecole Européenne de Chimie, Polymères et Matériaux (ECPM), 25 rue Becquerel, 67087, Strasbourg Cedex 2, France), Fax. nierengarten@unistra.fr.
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Nierengarten
authors.affiliation: Departamento de Química Orgánica, Universidad Autónoma de Madrid, 28049, Madrid, Spain), Fax. tomas.torres@uam.es.|IMDEA-Nanociencia, c/Faraday 9, Campus de Cantoblanco, 28049, Madrid, Spain. tomas.torres@uam.es.
authors.forename: Tomas
authors.initials: T
authors.lastname: Torres
authors.affiliation: Department of Chemistry and Pharmacy, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-, Nürnberg, Egerlandstrasse 3, 91058, Erlangen, Germany), Fax. dirk.guldi@fau.de.
authors.forename: Dirk M
authors.initials: DM
authors.lastname: Guldi
keywords: charge transfer; crown ethers; donor-acceptor systems; fullerenes; mass spectrometry; phthalocyanines