Probing Supramolecular Interactions between a Crown Ether Appended Zinc Phthalocyanine and an Ammonium Group Appended to a C60 Derivative

Lederer M, Hahn U, Strub JM, Cianferani S, Van Dorsselaer A, Nierengarten JF, Torres T, Guldi DM (2016)

Publication Type: Journal article

Publication year: 2016

Journal

Chemistry - A European Journal Wiley

Book Volume: 22

Pages Range: 2051-2059

Journal Issue: 6

DOI: 10.1002/chem.201503315

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 8.0×105 m-1 have 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 with CRIS profile

Marcus Lederer Lehrstuhl für Physikalische Chemie I Dirk Michael Guldi Lehrstuhl für Physikalische Chemie I

Involved external institutions

Universidad Autónoma de Madrid (UAM) ES Spain (ES) Université de Strasbourg (UDS) FR France (FR)

How to cite

APA:

Lederer, M., Hahn, U., Strub, J.-M., Cianferani, S., Van Dorsselaer, A., Nierengarten, J.-F.,... Guldi, D.M. (2016). Probing Supramolecular Interactions between a Crown Ether Appended Zinc Phthalocyanine and an Ammonium Group Appended to a C60 Derivative. Chemistry - A European Journal, 22(6), 2051-2059. https://doi.org/10.1002/chem.201503315

MLA:

Lederer, Marcus, et al. "Probing Supramolecular Interactions between a Crown Ether Appended Zinc Phthalocyanine and an Ammonium Group Appended to a C60 Derivative." Chemistry - A European Journal 22.6 (2016): 2051-2059.

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