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Synfacts 2013; 9(1): 0047
DOI: 10.1055/s-0032-1317892
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Poly(phenylacetylene)s with Pendant Sulfonamide Receptors for Anion Detection

Contributor(s):
Timothy M. Swager
,
Jens B. Ravnsbæk
Sakai R, Barasa EB, Sakai N, Sato S.-i, Satoh T, Kakuchi T * Hokkaido University, Sapporo, Japan
Colorimetric Detection of Anions in Aqueous Solution Using Poly(phenylacetylene) with Sulfonamide Receptors Activated by Electron-Withdrawing Group.

Macromolecules 2012;
45: 8221-8227
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Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

polyacetylenes - anion detection - sulfonamide receptors

Significance

Development of colorimetric sensors capable of detecting anions in aqueous medium is of great interest. In this paper, the authors describe the synthesis of a series of poly(phenylacetylene)s baring pendant sulfonamide side chains. The sulfonamide moiety is demonstrated to act as an anion receptor via a deprotonation mechanism, allowing sensing of anions in aqueous environment.


 

Comment

In this paper, the authors report a two-step protocol leading to a series of poly(phenylacetylene)s containing pendant sulfonamide ­moieties with electron-withdrawing or electron-donating substituents (2a–f). The obtained polymers showed varied PDIs (see Table above) in agreement with known rhodium-catalyzed polymerizations of acetylenes. They furthermore demonstrate the utility of these polymers as anion sensors. 2b showed clear red-shifted absorption upon addition of fluoride in mixed solvents with 20% water content.


 

 


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