期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 43, 页码 15377-15387出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201501260
关键词
chalcogens; heterocycles; luminescence; photophysics; supramolecular chemistry
资金
- Belgian National Research Foundation (FRFC) [2.4.550.09]
- Loterie Nationale
- TINTIN ARC project from the Belgian French community [09/14-023]
- Science Policy Office of the Belgian Federal Government [BELSPO-IAP 7/05]
- ERC
- CNR [PM.P04.010]
- MIUR [RBFR10DAK6, 2010CX2TLM]
The synthesis, X-ray crystal structures, ground- and excited-state UV/Vis absorption spectra, and luminescence properties of chalcogen-doped organic emitters equipped on both extremities with benzoxa-, benzothia-, benzoselena- and benzotellurazole (1(X) and 2(X)) moieties have been reported for the first time. The insertion of the four different chalcogen atoms within the same molecular skeleton enables the investigation of only the chalcogenic effect on the organisation and photophysical properties of the material. Detailed crystal-structure analyses provide evidence of similar packing for 2(O)-2(Se), in which the benzoazoles are engaged in - stacking and, for the heavier atoms, in secondary XX and XN bonding interactions. Detailed computational analysis shows that the arrangement is essentially governed by the interplay of van der Waals and secondary bonding interactions. Progressive quenching of the fluorescence and concomitant onset of phosphorescence features with gradually shorter lifetimes are detected as the atomic weight of the chalcogen heteroatom increases, with the tellurium-doped derivatives exhibiting only emission from the lowest triplet excited state. Notably, the phosphorescence spectra of the selenium and tellurium derivatives can be recorded even at room temperature; this is a very rare finding for fully organic emitters.
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