Colorimetric Ion Sensors Based on Polystyrenes Bearing Side Chain Triazole and Donor-Acceptor Chromophores

Analytical Sciences : the International Journal of the Japan Society for Analytical Chemistry
Yongrong LiTsuyoshi Michinobu

Abstract

Side chain clicked polystyrene derivatives formed by the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction showed colorimetric ion sensing behaviors when donor-acceptor chromophores, prepared by a [2+2] cylcoladdition-retroelectrocyclization between electron-rich alkynes and tetracyanoethylene (TCNE)/7,7,8,8-tetracyanoquinodimethane (TCNQ), were attached to the triazole rings. The metal ion sensing behaviors could be explained according to the theory of hard and soft acids and bases (HSAB). Hard acidic metal ions were mainly recognized by the hard basic anilino-nitrogen moieties, resulting in a decrease in the charge-transfer (CT) bands. In contrast, soft acidic metal ions led to a bathochromic shift in the CT bands due to the selective interactions with the soft basic cyano-nitrogen atoms. With the triazole spacers, more soft (and/or borderline) metal ions were recognized by the donor-acceptor chromophores probably due to more space for the various sized metal ions. The chemodocimetric anion sensing behaviors of the clicked polystyrenes were almost the same as those of the counter polystyrenes without the triazole spacers. Overall, the triazoles in this study do not serve as colorimetric sensor units towards both met...Continue Reading

References

Sep 1, 2005·Chemistry : a European Journal·Fabrizio MancinUmberto Tonellato
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Jun 24, 2010·Chemical Society Reviews·Anjun QinBen Zhong Tang
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Apr 12, 2011·Macromolecular Rapid Communications·Yusuke Washino, Tsuyoshi Michinobu
Sep 10, 2011·Macromolecular Rapid Communications·Yongrong LiTsuyoshi Michinobu
Dec 4, 2012·Physical Chemistry Chemical Physics : PCCP·Tsuyoshi MichinobuTsuyoshi Hyakutake
Aug 13, 2014·Angewandte Chemie·Jiajia DongK Barry Sharpless
Apr 15, 2015·Accounts of Chemical Research·Guillaume DelaittreChristopher Barner-Kowollik
Jul 30, 2015·Physical Chemistry Chemical Physics : PCCP·Alexander D MullinerKeith Refson
Oct 13, 2015·Physical Chemistry Chemical Physics : PCCP·Yusuke Washino, Tsuyoshi Michinobu

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