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

[Image: see text] 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-BMes(2)-SnBu(3)-benzene. Methylation of 1 led to the formation of the bisbenzimidazoli...

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Autores principales: Brazeau, Allison L., Yuan, Kang, Ko, Soo-Byung, Wyman, Ian, Wang, Suning
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6645667/
https://www.ncbi.nlm.nih.gov/pubmed/31457395
http://dx.doi.org/10.1021/acsomega.7b01631
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author Brazeau, Allison L.
Yuan, Kang
Ko, Soo-Byung
Wyman, Ian
Wang, Suning
author_facet Brazeau, Allison L.
Yuan, Kang
Ko, Soo-Byung
Wyman, Ian
Wang, Suning
author_sort Brazeau, Allison L.
collection PubMed
description [Image: see text] 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-BMes(2)-SnBu(3)-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 × 10(4) to 5 × 10(5) 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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spelling pubmed-66456672019-08-27 Anion Sensing with a Blue Fluorescent Triarylboron-Functionalized Bisbenzimidazole and Its Bisbenzimidazolium Salt Brazeau, Allison L. Yuan, Kang Ko, Soo-Byung Wyman, Ian Wang, Suning ACS Omega [Image: see text] 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-BMes(2)-SnBu(3)-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 × 10(4) to 5 × 10(5) 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. American Chemical Society 2017-12-04 /pmc/articles/PMC6645667/ /pubmed/31457395 http://dx.doi.org/10.1021/acsomega.7b01631 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Brazeau, Allison L.
Yuan, Kang
Ko, Soo-Byung
Wyman, Ian
Wang, Suning
Anion Sensing with a Blue Fluorescent Triarylboron-Functionalized Bisbenzimidazole and Its Bisbenzimidazolium Salt
title Anion Sensing with a Blue Fluorescent Triarylboron-Functionalized Bisbenzimidazole and Its Bisbenzimidazolium Salt
title_full Anion Sensing with a Blue Fluorescent Triarylboron-Functionalized Bisbenzimidazole and Its Bisbenzimidazolium Salt
title_fullStr Anion Sensing with a Blue Fluorescent Triarylboron-Functionalized Bisbenzimidazole and Its Bisbenzimidazolium Salt
title_full_unstemmed Anion Sensing with a Blue Fluorescent Triarylboron-Functionalized Bisbenzimidazole and Its Bisbenzimidazolium Salt
title_short Anion Sensing with a Blue Fluorescent Triarylboron-Functionalized Bisbenzimidazole and Its Bisbenzimidazolium Salt
title_sort anion sensing with a blue fluorescent triarylboron-functionalized bisbenzimidazole and its bisbenzimidazolium salt
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6645667/
https://www.ncbi.nlm.nih.gov/pubmed/31457395
http://dx.doi.org/10.1021/acsomega.7b01631
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