Dithiafulvenyl‐Extended N‐Heterotriangulenes and Their Interaction with C60: Cooperative Fluorescence. Issue 50 (1st August 2017)

• Record Type: Journal Article
• 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
• Is Part Of: Chemistry. Volume 23:Issue 50(2017)
• Page Start: 12353
• Page End: 12362
• Publication Date: 2017-08-01
• Subjects: 1, 3-dithiafulvene -- electrochemistry -- fluorescence -- fullerenes -- N-heterotriangulenes; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201701625
• Languages: English
• ISSNs: 0947-6539

Abstract

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 10 4 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. Abstract : 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.