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Anion Sensing with a Blue Fluorescent Triarylboron-Functionalized Bisbenzimidazole and Its Bisbenzimidazolium Salt
Allison L Brazeau1, Kang Yuan1, Soo-Byung Ko1
1Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada.
Abstract:
A blue fluorescent p-dimesitylboryl-phenyl-functionalized 1,3-bisbenzimidazolyl benzene molecule (1) has been synthesized in high yield by Stille coupling of bisbenzimidazolyl bromobenzene with p-BMes2-SnBu3-benzene. Methylation of 1 led to the formation of the bisbenzimidazolium salt (2). The utility of both 1 and 2 in sensing CN- and halide (F-, Cl-, Br-, and I-) was examined, and it was found that only the small fluoride and cyanide anions were able to bind to the boron atom with binding constants in the range of 2.9 × 104 to 5 × 105 M-1. Computational studies provided insight into the photophysical properties of the molecules and verified that a charge-transfer process is quenched in these "turn-off" molecular sensors.
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