期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 18, 期 22, 页码 6764-6775出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201103954
关键词
charge transfer; copper; cross-coupling; perylenes bisimides; Ullmann reaction
资金
- National Natural Science Foundation of China [91027043, 21021091]
- 973 Program [2011CB932301]
- NSFC-DFG [TRR61]
- Chinese Academy of Sciences
- Deutsche Forschungsgemeinschaft [Graduiertenkolleg GRK 1221]
- PRIN [2008 JKBBK4]
The copper-mediated Ullmann coupling of 1,7-dibromoperylene bisimides afforded structurally perfect singly-linked perylene bisimide (PBI) arrays, whilst the homo-coupling of 1,12-dibromoperylene bisimides gave doubly-linked and triply-linked diperylene bisimides. The interactions of three bay-linked diperylene bisimides that differed in their linkage (singly, doubly, and triply) were investigated in their neutral and reduced forms (mono-anion to tetra-anion). UV/Vis absorption and fluorescence spectroscopy revealed different degrees of interaction, which was explained by exciton coupling and conjugation effects. The electrochemical properties and spectroelectrochemistry also showed quite-different degrees of PBI interactions in the reduced mixed-valence species, which was apparent by the observation of CT bands. The interpretation of the experimental findings was supported by spin-restricted and -unrestricted DFT and time-dependent TD-DFT calculations with the long-range-corrected CAM-B3LYP functional. Accordingly, the degree of interaction in both the neutral and reduced forms of the bay-linked PBIs was qualitatively in the order doubly linked
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