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D–π–A Triarylboron Compounds with Tunable Push–Pull Character Achieved by Modification of Both the Donor and Acceptor Moieties
Author(s) -
Zhang Zuolun,
Edkins Robert M.,
Nitsch Jörn,
Fucke Katharina,
Eichhorn Antonius,
Steffen Andreas,
Wang Yue,
Marder Todd B.
Publication year - 2015
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.201405621
Subject(s) - triphenylamine , borylation , acceptor , photochemistry , chemistry , fluorescence , boron , electrochemistry , adduct , organic chemistry , electrode , alkyl , physics , quantum mechanics , aryl , condensed matter physics
The push–pull character of a series of donor–bithienyl–acceptor compounds has been tuned by adopting triphenylamine or 1,1,7,7‐tetramethyljulolidine as a donor and B(2,6‐Me 2 ‐4‐RC 6 H 2 ) 2 (R=Me, C 6 F 5 or 3,5‐(CF 3 ) 2 C 6 H 3 ) or B[2,4,6‐(CF 3 ) 3 C 6 H 2 ] 2 as an acceptor. Ir‐catalyzed CH borylation was utilized in the derivatization of the boryl acceptors and the tetramethyljulolidine donor. The donor and acceptor strengths were evaluated by electrochemical and photophysical measurements. In solution, the compound with the strongest acceptor, B[2,4,6‐(CF 3 ) 3 C 6 H 2 ] 2 ((FMes) 2 B), has strongly quenched emission, while all other compounds show efficient green to red ( Φ F =0.80–1.00) or near‐IR (NIR; Φ F =0.27–0.48) emission, depending on solvent. Notably, this study presents the first examples of efficient NIR emission from three‐coordinate boron compounds. Efficient solid‐state red emission was observed for some derivatives, and interesting aggregation‐induced emission of the (FMes) 2 B‐containing compound was studied. Moreover, each compound showed a strong and clearly visible response to fluoride addition, with either a large emission‐color change or turn‐on fluorescence.