Fluoride ion sensing with an acridinium borane Academic Article uri icon

abstract

  • With our continuing interest in the chemistry of cationic boranes, we have synthesized the tetrafluoroborate salt of 1-dimesitylboron-4-( N-methyl-9-acridinium)-phenylene, which acts as a turn-on fluoride anion sensor, visibly changing from yellow to orange upon binding fluoride. To understand this reactivity, we spectroscopically and computationally analyzed the cation and fluoroborate adduct. Ultravioletvisible spectroscopy and time-dependent density functional theory calculations revealed the basis of the color change to be a low energy redshift in a intramolecular charge transfer band. Electrochemical studies were undertaken to further probe this system. Cyclic voltammetry indicated a reversible one-electron reduction for the cation and a cathodic shift of0.12V in the first reduction wave upon fluoride binding. Chemical reduction of the cation yielded the acridine borane radical, which was verified by electron paramagnetic resonance spectroscopy.

published proceedings

  • CANADIAN JOURNAL OF CHEMISTRY

author list (cited authors)

  • Liu, W., & Gabbai, F. P.

citation count

  • 1

complete list of authors

  • Liu, Wei-Chun||Gabbaii, Francois P

publication date

  • March 2022