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Ionic liquid inspired alkalinochromic salts based on Reichardt’s dyes for the solution phase and vapochromic detection of amines

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Abstract

Chromogenic salts based on the negatively solvatochromic pyridinium N-phenolate betaines 2,6-diphenyl-4-(2,4,6-triphenyl-N-pyridino)-phenolate (Reichardt’s dye 30) and 2,6-dichloro-4-(2,4,6-triphenyl-N-pyridino)-phenolate (Reichardt’s dye 33) proved to be promising probes for the colorimetric detection of bases, including hydroxide ion, ammonia, and aliphatic amines. Specifically, the protonated halide forms of these two dyes were ion exchanged to generate lipophilic bis(trifluoromethylsulfonyl)imide derivatives, denoted [ET(30)][Tf2N] and [ET(33)][Tf2N], respectively. When dissolved in 95 vol% EtOH, these essentially colorless solutions displayed dramatic “alkalinochromic” color-on switching due to phenolic deprotonation to generate the zwitterionic form of the dyes with their characteristic charge-transfer absorption. The extent of the colorimetric response varied with the base strength for the aliphatic amines tested (i.e., propylamine, ethanolamine, ethylenediamine, diethylenetriamine, triethylamine, triethanolamine), being loosely correlated with the pKb of the amine. In addition, we demonstrated proof of concept for the vapochromic detection of ammonia and aliphatic amines by dissolution of the chromogenic probes in the ionic liquid 1-propyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide. We also showed that the dyed ionic liquid can be successfully immobilized within silica sol-gel ionogels to generate more practical and robust sensory platforms. This strategy represents a useful addition to existing colorimetric sensor arrays targeting amines and other basic species. In particular, the differential response of the two different probes offers a measure of chemical selectivity which will be of interest for detecting biogenic amines in food safety applications, among other areas.

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Acknowledgements

G. Baker acknowledges support for this research from the Research Corporation for Science Advancement. The authors thank Dr. Sudhir Ravula for helpful feedback and thoughtful discussions.

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Authors and Affiliations

  1. Department of Chemistry, University of Missouri-Columbia, 601 S. College Ave., Chemistry Building, Columbia, MO, 65211, USA

    Jeremy B. Essner & Gary A. Baker

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  1. Jeremy B. Essner
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Correspondence to Gary A. Baker.

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Published in the topical collection Ionic Liquids as Tunable Materials in (Bio)Analytical Chemistry with guest editors Jared L. Anderson and Kevin D. Clark.

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Essner, J.B., Baker, G.A. Ionic liquid inspired alkalinochromic salts based on Reichardt’s dyes for the solution phase and vapochromic detection of amines. Anal Bioanal Chem 410, 4607–4613 (2018). https://doi.org/10.1007/s00216-018-1177-5

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  • DOI: https://doi.org/10.1007/s00216-018-1177-5

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