Premium
Dithiafulvenyl‐Extended N ‐Heterotriangulenes and Their Interaction with C 60 : Cooperative Fluorescence
Author(s) -
Gliemann Bettina D.,
Strauss Volker,
Hitzenberger Jakob F.,
Dral Pavlo O.,
Hampel Frank,
Gisselbrecht JeanPaul,
Drewello Thomas,
Thiel Walter,
Guldi Dirk M.,
Kivala Milan
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701625
Subject(s) - supramolecular chemistry , fluorescence , chemistry , cyclic voltammetry , fluorescence spectroscopy , fullerene , electron acceptor , acceptor , mass spectrometry , photochemistry , crystallography , electrochemistry , crystal structure , organic chemistry , physics , electrode , quantum mechanics , chromatography , condensed matter physics
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 60 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 60 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 4 m −1 . Supportive results for the supramolecular assembly of both N ‐heterotriangulenes with C 60 were obtained by ESI mass spectrometric investigations in the gas phase.