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Anion Sensing with a Blue Fluorescent Triarylboron-Functionalized Bisbenzimidazole and Its Bisbenzimidazolium Salt.

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.

SUBMITTER: Brazeau AL

PROVIDER: S-EPMC6645667 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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Anion Sensing with a Blue Fluorescent Triarylboron-Functionalized Bisbenzimidazole and Its Bisbenzimidazolium Salt.

Brazeau Allison L AL Yuan Kang K Ko Soo-Byung SB Wyman Ian I Wang Suning S

ACS omega 20171204 12

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 ex ...[more]

PMID: 31457395

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