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Chloromethyl-modified Ru(ii) complexes enabling large pH jumps at low concentrations through photoinduced hydrolysis

Photoacid generators (PAGs) are finding increasing applications in spatial and temporal modulation of biological events in vitro and in vivo. In these applications, large pH jumps at low PAG concentrations are of great importance to achieve maximal expected manipulation but minimal unwanted interfer...

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Autores principales: Tian, Na, Sun, Weize, Feng, Yang, Guo, Xusheng, Lu, Jian, Li, Chao, Hou, Yuanjun, Wang, Xuesong, Zhou, Qianxiong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7066672/
https://www.ncbi.nlm.nih.gov/pubmed/32190237
http://dx.doi.org/10.1039/c9sc03957k
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author Tian, Na
Sun, Weize
Feng, Yang
Guo, Xusheng
Lu, Jian
Li, Chao
Hou, Yuanjun
Wang, Xuesong
Zhou, Qianxiong
author_facet Tian, Na
Sun, Weize
Feng, Yang
Guo, Xusheng
Lu, Jian
Li, Chao
Hou, Yuanjun
Wang, Xuesong
Zhou, Qianxiong
author_sort Tian, Na
collection PubMed
description Photoacid generators (PAGs) are finding increasing applications in spatial and temporal modulation of biological events in vitro and in vivo. In these applications, large pH jumps at low PAG concentrations are of great importance to achieve maximal expected manipulation but minimal unwanted interference. To this end, both high photoacid quantum yield and capacity are essential, where the capacity refers to the proton number that a PAG molecule can release. Up to now, most PAGs only produce one proton for each molecule. In this work, the hydrolysis reaction of benzyl chlorides was successfully leveraged to develop a novel type of PAG. Upon visible light irradiation, Ru(ii) polypyridyl complexes modified with chloromethyl groups can undergo full hydrolysis with photoacid quantum yield as high as 0.6. Depending on the number of the chloromethyl groups, the examined Ru(ii) complexes can release multiple protons per molecule, leading to large pH jumps at very low PAG concentrations, a feature particularly favorable for bio-related applications.
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spelling pubmed-70666722020-03-18 Chloromethyl-modified Ru(ii) complexes enabling large pH jumps at low concentrations through photoinduced hydrolysis Tian, Na Sun, Weize Feng, Yang Guo, Xusheng Lu, Jian Li, Chao Hou, Yuanjun Wang, Xuesong Zhou, Qianxiong Chem Sci Chemistry Photoacid generators (PAGs) are finding increasing applications in spatial and temporal modulation of biological events in vitro and in vivo. In these applications, large pH jumps at low PAG concentrations are of great importance to achieve maximal expected manipulation but minimal unwanted interference. To this end, both high photoacid quantum yield and capacity are essential, where the capacity refers to the proton number that a PAG molecule can release. Up to now, most PAGs only produce one proton for each molecule. In this work, the hydrolysis reaction of benzyl chlorides was successfully leveraged to develop a novel type of PAG. Upon visible light irradiation, Ru(ii) polypyridyl complexes modified with chloromethyl groups can undergo full hydrolysis with photoacid quantum yield as high as 0.6. Depending on the number of the chloromethyl groups, the examined Ru(ii) complexes can release multiple protons per molecule, leading to large pH jumps at very low PAG concentrations, a feature particularly favorable for bio-related applications. Royal Society of Chemistry 2019-10-24 /pmc/articles/PMC7066672/ /pubmed/32190237 http://dx.doi.org/10.1039/c9sc03957k Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Tian, Na
Sun, Weize
Feng, Yang
Guo, Xusheng
Lu, Jian
Li, Chao
Hou, Yuanjun
Wang, Xuesong
Zhou, Qianxiong
Chloromethyl-modified Ru(ii) complexes enabling large pH jumps at low concentrations through photoinduced hydrolysis
title Chloromethyl-modified Ru(ii) complexes enabling large pH jumps at low concentrations through photoinduced hydrolysis
title_full Chloromethyl-modified Ru(ii) complexes enabling large pH jumps at low concentrations through photoinduced hydrolysis
title_fullStr Chloromethyl-modified Ru(ii) complexes enabling large pH jumps at low concentrations through photoinduced hydrolysis
title_full_unstemmed Chloromethyl-modified Ru(ii) complexes enabling large pH jumps at low concentrations through photoinduced hydrolysis
title_short Chloromethyl-modified Ru(ii) complexes enabling large pH jumps at low concentrations through photoinduced hydrolysis
title_sort chloromethyl-modified ru(ii) complexes enabling large ph jumps at low concentrations through photoinduced hydrolysis
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7066672/
https://www.ncbi.nlm.nih.gov/pubmed/32190237
http://dx.doi.org/10.1039/c9sc03957k
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