Dithiafulvenyl-Extended N-Heterotriangulenes and Their Interaction with C60: Cooperative Fluorescence

Gliemann B, Strauß V, Hitzenberger J, Dral PO, Hampel F, Gisselbrecht JP, Drewello T, Thiel W, Guldi DM, Kivala M (2017)

Publication Type: Journal article

Publication year: 2017

Journal

Chemistry - A European Journal Wiley

Book Volume: 23

Pages Range: 12353-12362

Journal Issue: 50

DOI: 10.1002/chem.201701625

Abstract

We describe the synthesis as well as the electronic and photophysical characterization of novel N-heterotriangulene derivatives decorated with methoxycarbonyl- and methyl-sulfanyl-substituted dithiafulvenyl moieties. The association of these electron-rich compounds with fullerene C60 as electron acceptor was investigated by means of photophysical, voltammetric, and mass spectrometric methods and rationalized by DFT calculations. Importantly, light-induced interactions between the dithiafulvene-substituted N-heterotriangulene bearing methoxycarbonyl substituents with C60 leads to cooperative fluorescence. Quantitative Job plot analyses by means of fluorescence spectroscopy and voltammetry confirm a 1:1 association with binding constants in the order of 104  m-1. Supportive results for the supramolecular assembly of both N-heterotriangulenes with C60 were obtained by ESI mass spectrometric investigations in the gas phase.

Authors with CRIS profile

Bettina Gliemann Lehrstuhl für Organische Chemie I Volker Strauß Interdisziplinäres Zentrum für Molekulare Materialien Jakob Hitzenberger Professur für Physikalische Chemie Frank Hampel Lehrstuhl für Organische Chemie I Thomas Drewello Professur für Physikalische Chemie Dirk Michael Guldi Lehrstuhl für Physikalische Chemie I Milan Kivala Lehrstuhl für Organische Chemie I

Additional Organisation(s)

Exzellenz-Cluster Engineering of Advanced Materials

Involved external institutions

Max-Planck-Institut für Kohlenforschung (MPI KoFo) / Max Planck Institute for Coal Research DE Germany (DE) Université de Strasbourg (UDS) FR France (FR)

How to cite

APA:

Gliemann, B., Strauß, V., Hitzenberger, J., Dral, P.O., Hampel, F., Gisselbrecht, J.-P.,... Kivala, M. (2017). Dithiafulvenyl-Extended N-Heterotriangulenes and Their Interaction with C60: Cooperative Fluorescence. Chemistry - A European Journal, 23(50), 12353-12362. https://dx.doi.org/10.1002/chem.201701625

MLA:

Gliemann, Bettina, et al. "Dithiafulvenyl-Extended N-Heterotriangulenes and Their Interaction with C60: Cooperative Fluorescence." Chemistry - A European Journal 23.50 (2017): 12353-12362.

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