Application of heterocyclic polymers in the ratiometric spectrophotometric determination of fluoride

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Abstract

Herein we report the use of heterocyclic functional polymers in the ratiometric spectrophotometric determination of fluoride (F-). Polymers incorporating benzo[d][1,2,3]triazole moieties linked to the polymer backbone via urea links are demonstrated to have utility for the ratiometric detection of the F- ion, with a detection limit in the order of ∼2 μM. The hydrogen-bonding recognition between the benzo[d][1,2,3]triazole moiety and F- ion was investigated using UV-vis spectrophotometry and NMR analysis. The importance of the urea linkage was elucidated by investigating a second benzo[d][1,2,3]triazole functional monomer wherein the heterocyclic group is attached to the polymerizable group via a carbamate linkage. The replacement of the urea link with a carbamate group led to significantly reduced F- sensitivity. Moreover, by examining an analogous benzo[d]imidazole monomer it was demonstrated that having a nitrogen atom in the 2-position of the heterocycle was important for maximizing the sensitivity of the assay. Taken together, these results demonstrated that the urea-substituted benzo[d][1,2,3]triazole motif greatly enhances F- ion detection. Importantly, the F- ion sensing capability of the monomer is retained after incorporating into a diblock copolymer using reversible addition-fragmentation chain transfer (RAFT) polymerization
Original languageEnglish
Pages (from-to)236-241
Number of pages6
JournalACS Macro Letters
Volume4
Issue number2
DOIs
Publication statusPublished - 2015

Cite this

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title = "Application of heterocyclic polymers in the ratiometric spectrophotometric determination of fluoride",
abstract = "Herein we report the use of heterocyclic functional polymers in the ratiometric spectrophotometric determination of fluoride (F-). Polymers incorporating benzo[d][1,2,3]triazole moieties linked to the polymer backbone via urea links are demonstrated to have utility for the ratiometric detection of the F- ion, with a detection limit in the order of ∼2 μM. The hydrogen-bonding recognition between the benzo[d][1,2,3]triazole moiety and F- ion was investigated using UV-vis spectrophotometry and NMR analysis. The importance of the urea linkage was elucidated by investigating a second benzo[d][1,2,3]triazole functional monomer wherein the heterocyclic group is attached to the polymerizable group via a carbamate linkage. The replacement of the urea link with a carbamate group led to significantly reduced F- sensitivity. Moreover, by examining an analogous benzo[d]imidazole monomer it was demonstrated that having a nitrogen atom in the 2-position of the heterocycle was important for maximizing the sensitivity of the assay. Taken together, these results demonstrated that the urea-substituted benzo[d][1,2,3]triazole motif greatly enhances F- ion detection. Importantly, the F- ion sensing capability of the monomer is retained after incorporating into a diblock copolymer using reversible addition-fragmentation chain transfer (RAFT) polymerization",
author = "Jinming Hu and Whittaker, {Michael R} and Davis, {Thomas P} and John Quinn",
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journal = "ACS Macro Letters",
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Application of heterocyclic polymers in the ratiometric spectrophotometric determination of fluoride. / Hu, Jinming; Whittaker, Michael R; Davis, Thomas P; Quinn, John.

In: ACS Macro Letters, Vol. 4, No. 2, 2015, p. 236-241.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - Application of heterocyclic polymers in the ratiometric spectrophotometric determination of fluoride

AU - Hu, Jinming

AU - Whittaker, Michael R

AU - Davis, Thomas P

AU - Quinn, John

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N2 - Herein we report the use of heterocyclic functional polymers in the ratiometric spectrophotometric determination of fluoride (F-). Polymers incorporating benzo[d][1,2,3]triazole moieties linked to the polymer backbone via urea links are demonstrated to have utility for the ratiometric detection of the F- ion, with a detection limit in the order of ∼2 μM. The hydrogen-bonding recognition between the benzo[d][1,2,3]triazole moiety and F- ion was investigated using UV-vis spectrophotometry and NMR analysis. The importance of the urea linkage was elucidated by investigating a second benzo[d][1,2,3]triazole functional monomer wherein the heterocyclic group is attached to the polymerizable group via a carbamate linkage. The replacement of the urea link with a carbamate group led to significantly reduced F- sensitivity. Moreover, by examining an analogous benzo[d]imidazole monomer it was demonstrated that having a nitrogen atom in the 2-position of the heterocycle was important for maximizing the sensitivity of the assay. Taken together, these results demonstrated that the urea-substituted benzo[d][1,2,3]triazole motif greatly enhances F- ion detection. Importantly, the F- ion sensing capability of the monomer is retained after incorporating into a diblock copolymer using reversible addition-fragmentation chain transfer (RAFT) polymerization

AB - Herein we report the use of heterocyclic functional polymers in the ratiometric spectrophotometric determination of fluoride (F-). Polymers incorporating benzo[d][1,2,3]triazole moieties linked to the polymer backbone via urea links are demonstrated to have utility for the ratiometric detection of the F- ion, with a detection limit in the order of ∼2 μM. The hydrogen-bonding recognition between the benzo[d][1,2,3]triazole moiety and F- ion was investigated using UV-vis spectrophotometry and NMR analysis. The importance of the urea linkage was elucidated by investigating a second benzo[d][1,2,3]triazole functional monomer wherein the heterocyclic group is attached to the polymerizable group via a carbamate linkage. The replacement of the urea link with a carbamate group led to significantly reduced F- sensitivity. Moreover, by examining an analogous benzo[d]imidazole monomer it was demonstrated that having a nitrogen atom in the 2-position of the heterocycle was important for maximizing the sensitivity of the assay. Taken together, these results demonstrated that the urea-substituted benzo[d][1,2,3]triazole motif greatly enhances F- ion detection. Importantly, the F- ion sensing capability of the monomer is retained after incorporating into a diblock copolymer using reversible addition-fragmentation chain transfer (RAFT) polymerization

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