TY - JOUR
T1 - D-π-A triarylboron compounds with tunable push-pull character achieved by modification of both the donor and acceptor moieties
AU - Zhang, Zuolun
AU - Edkins, Robert M.
AU - Nitsch, Jörn
AU - Fucke, Katharina
AU - Eichhorn, Antonius
AU - Steffen, Andreas
AU - Wang, Yue
AU - Marder, Todd B.
PY - 2015/1/2
Y1 - 2015/1/2
N2 - 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-Me2-4-RC6H2)2 (R=Me, C6F5 or 3,5-(CF3)2C6H3) or B[2,4,6-(CF3)3C6H2]2 as an acceptor. Ir-catalyzed C-H 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-(CF3)3C6H2]2 ((FMes)2B), has strongly quenched emission, while all other compounds show efficient green to red (ΦF=0.80-1.00) or near-IR (NIR; ΦF= 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 solidstate red emission was observed for some derivatives, and interesting aggregation-induced emission of the (FMes)2Bcontaining 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.
AB - 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-Me2-4-RC6H2)2 (R=Me, C6F5 or 3,5-(CF3)2C6H3) or B[2,4,6-(CF3)3C6H2]2 as an acceptor. Ir-catalyzed C-H 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-(CF3)3C6H2]2 ((FMes)2B), has strongly quenched emission, while all other compounds show efficient green to red (ΦF=0.80-1.00) or near-IR (NIR; ΦF= 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 solidstate red emission was observed for some derivatives, and interesting aggregation-induced emission of the (FMes)2Bcontaining 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.
KW - boron
KW - charge transfer
KW - fluorescence
KW - near infrared
KW - photophysics
UR - http://www.scopus.com/inward/record.url?scp=84920409339&partnerID=8YFLogxK
U2 - 10.1002/chem.201405621
DO - 10.1002/chem.201405621
M3 - Article
C2 - 25413782
AN - SCOPUS:84920409339
SN - 0947-6539
VL - 21
SP - 177
EP - 190
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 1
ER -