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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2017
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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. |
format | Online Article Text |
id | pubmed-6645667 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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