D-π-A triarylboron compounds with tunable push-pull character achieved by modification of both the donor and acceptor moieties

Zuolun Zhang, Robert M. Edkins, Jörn Nitsch, Katharina Fucke, Antonius Eichhorn, Andreas Steffen, Yue Wang, Todd B. Marder

Research output: Contribution to journalArticle

86 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)177-190
Number of pages14
JournalChemistry - A European Journal
Volume21
Issue number1
DOIs
Publication statusPublished - 2 Jan 2015

Keywords

  • boron
  • charge transfer
  • fluorescence
  • near infrared
  • photophysics

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