Cargando…

Dynamic Covalent Chemistry-based Sensing: Pyrenyl Derivatives of Phenylboronic Acid for Saccharide and Formaldehyde

We synthesized two specially designed pyrenyl (Py) derivatives of phenylboronic acid, PSNB1 and PSNB2, of which PSNB2 self-assemble to form dynamic aggregate in methanol-water mixture (1:99, v/v) via intermolecular H-bonding and pi-pi stacking. Interestingly, the dynamic aggregate shows smart respon...

Descripción completa

Detalles Bibliográficos
Autores principales: Chang, Xingmao, Fan, Jiayun, Wang, Min, Wang, Zhaolong, Peng, Haonan, He, Gang, Fang, Yu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4976341/
https://www.ncbi.nlm.nih.gov/pubmed/27498703
http://dx.doi.org/10.1038/srep31187
_version_ 1782446856724283392
author Chang, Xingmao
Fan, Jiayun
Wang, Min
Wang, Zhaolong
Peng, Haonan
He, Gang
Fang, Yu
author_facet Chang, Xingmao
Fan, Jiayun
Wang, Min
Wang, Zhaolong
Peng, Haonan
He, Gang
Fang, Yu
author_sort Chang, Xingmao
collection PubMed
description We synthesized two specially designed pyrenyl (Py) derivatives of phenylboronic acid, PSNB1 and PSNB2, of which PSNB2 self-assemble to form dynamic aggregate in methanol-water mixture (1:99, v/v) via intermolecular H-bonding and pi-pi stacking. Interestingly, the dynamic aggregate shows smart response to presence of fructose (F) as evidenced by fluorescence color change from green to blue. More interestingly, the fluorescence emission of the resulted PSNB2-F changes from blue to green with the addition of formaldehyde (FA). The reason behind is formation of a PSNB2-F dimer via FA cross-linking. Based upon the reactions as found, sensitive and fast sensing of F and FA in water was realized, of which the experimental DLs could be significantly lower than 10 μM for both analytes, and the response times are less than 1 min. It is believed that not only the materials as created may have the potential to find real-life applications but also the strategy as developed can be adopted to develop other dynamic materials.
format Online
Article
Text
id pubmed-4976341
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher Nature Publishing Group
record_format MEDLINE/PubMed
spelling pubmed-49763412016-08-22 Dynamic Covalent Chemistry-based Sensing: Pyrenyl Derivatives of Phenylboronic Acid for Saccharide and Formaldehyde Chang, Xingmao Fan, Jiayun Wang, Min Wang, Zhaolong Peng, Haonan He, Gang Fang, Yu Sci Rep Article We synthesized two specially designed pyrenyl (Py) derivatives of phenylboronic acid, PSNB1 and PSNB2, of which PSNB2 self-assemble to form dynamic aggregate in methanol-water mixture (1:99, v/v) via intermolecular H-bonding and pi-pi stacking. Interestingly, the dynamic aggregate shows smart response to presence of fructose (F) as evidenced by fluorescence color change from green to blue. More interestingly, the fluorescence emission of the resulted PSNB2-F changes from blue to green with the addition of formaldehyde (FA). The reason behind is formation of a PSNB2-F dimer via FA cross-linking. Based upon the reactions as found, sensitive and fast sensing of F and FA in water was realized, of which the experimental DLs could be significantly lower than 10 μM for both analytes, and the response times are less than 1 min. It is believed that not only the materials as created may have the potential to find real-life applications but also the strategy as developed can be adopted to develop other dynamic materials. Nature Publishing Group 2016-08-08 /pmc/articles/PMC4976341/ /pubmed/27498703 http://dx.doi.org/10.1038/srep31187 Text en Copyright © 2016, The Author(s) http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Chang, Xingmao
Fan, Jiayun
Wang, Min
Wang, Zhaolong
Peng, Haonan
He, Gang
Fang, Yu
Dynamic Covalent Chemistry-based Sensing: Pyrenyl Derivatives of Phenylboronic Acid for Saccharide and Formaldehyde
title Dynamic Covalent Chemistry-based Sensing: Pyrenyl Derivatives of Phenylboronic Acid for Saccharide and Formaldehyde
title_full Dynamic Covalent Chemistry-based Sensing: Pyrenyl Derivatives of Phenylboronic Acid for Saccharide and Formaldehyde
title_fullStr Dynamic Covalent Chemistry-based Sensing: Pyrenyl Derivatives of Phenylboronic Acid for Saccharide and Formaldehyde
title_full_unstemmed Dynamic Covalent Chemistry-based Sensing: Pyrenyl Derivatives of Phenylboronic Acid for Saccharide and Formaldehyde
title_short Dynamic Covalent Chemistry-based Sensing: Pyrenyl Derivatives of Phenylboronic Acid for Saccharide and Formaldehyde
title_sort dynamic covalent chemistry-based sensing: pyrenyl derivatives of phenylboronic acid for saccharide and formaldehyde
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4976341/
https://www.ncbi.nlm.nih.gov/pubmed/27498703
http://dx.doi.org/10.1038/srep31187
work_keys_str_mv AT changxingmao dynamiccovalentchemistrybasedsensingpyrenylderivativesofphenylboronicacidforsaccharideandformaldehyde
AT fanjiayun dynamiccovalentchemistrybasedsensingpyrenylderivativesofphenylboronicacidforsaccharideandformaldehyde
AT wangmin dynamiccovalentchemistrybasedsensingpyrenylderivativesofphenylboronicacidforsaccharideandformaldehyde
AT wangzhaolong dynamiccovalentchemistrybasedsensingpyrenylderivativesofphenylboronicacidforsaccharideandformaldehyde
AT penghaonan dynamiccovalentchemistrybasedsensingpyrenylderivativesofphenylboronicacidforsaccharideandformaldehyde
AT hegang dynamiccovalentchemistrybasedsensingpyrenylderivativesofphenylboronicacidforsaccharideandformaldehyde
AT fangyu dynamiccovalentchemistrybasedsensingpyrenylderivativesofphenylboronicacidforsaccharideandformaldehyde