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Journal Article

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

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Dral,  Pavlo O.
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Thiel,  Walter
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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chem201701625-sup-0001-misc_information.pdf
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Citation

Gliemann, B. D., Strauss, V., Hitzenberger, J. F., Dral, P. O., Hampel, F., Gisselbrecht, J.-P., et al. (2017). Dithiafulvenyl-Extended N-Heterotriangulenes and Their Interaction with C60: Cooperative Fluorescence. Chemistry – A European Journal, 23(50), 12353-12362. doi:10.1002/chem.201701625.


Cite as: https://hdl.handle.net/11858/00-001M-0000-002E-9D27-E
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.