Dithiafulvenyl-Extended N-Heterotriangulenes and Their Interaction with C 60 : Cooperative Fluorescence

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 C as electron accep...

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Bibliographic Details
Published in:Chemistry : a European journal 2017-09, Vol.23 (50), p.12353-12362
Main Authors: Gliemann, Bettina D, Strauss, Volker, Hitzenberger, Jakob F, Dral, Pavlo O, Hampel, Frank, Gisselbrecht, Jean-Paul, Drewello, Thomas, Thiel, Walter, Guldi, Dirk M, Kivala, Milan
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
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Summary: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 C 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 C 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 10  m . Supportive results for the supramolecular assembly of both N-heterotriangulenes with C were obtained by ESI mass spectrometric investigations in the gas phase.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201701625