Chemistry - A European Journal
Chemistry - A European Journal
5 years ago

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

Dithiafulvenyl-Extended N-Heterotriangulenes and Their Interaction with C60: Cooperative Fluorescence
Thomas Drewello, Frank Hampel, Walter Thiel, Pavlo O. Dral, Jean-Paul Gisselbrecht, Bettina D. Gliemann, Dirk M. Guldi, Jakob F. Hitzenberger, Volker Strauss, Milan Kivala
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. Enlightened association: Electron-rich N-heterotriangulenes featuring dithiafulvenyl moieties were synthesized and their association with C60 resulting in cooperative fluorescence was studied by photophysical, voltammetric, and mass spectrometric methods and rationalized by DFT calculations.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701625

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