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Ionic liquid inspired alkalinochromic salts based on Reichardt’s dyes for the solution phase and vapochromic detection of amines
Analytical and Bioanalytical Chemistry ( IF 4.3 ) Pub Date : 2018-06-27 , DOI: 10.1007/s00216-018-1177-5
Jeremy B. Essner , Gary A. Baker

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.



中文翻译:

离子液体激发的基于Reichardt染料的碱铬盐用于溶液相和气相色谱法检测胺

基于负溶剂化变色吡啶鎓N-酚盐的发色盐可生成2,6-二苯基-4-(2,4,6-三苯基-N-吡啶基)-酚盐(雷卡特染料30)和2,6-二氯-4-( 2,4,6-三苯基-N-吡啶基)-酚盐(雷卡德染料33)被证明是比色法检测碱的探针,这些碱包括氢氧根离子,氨和脂族胺。具体而言,将这两种染料的质子化卤化物形式进行离子交换以生成亲脂性双(三氟甲基磺酰基)酰亚胺衍生物,分别表示为[ E T(30)] [Tf 2 N]和[ E T(33)] [Tf 2N]。当溶于95%(体积)的EtOH中时,由于酚类去质子化作用,这些基本无色的溶液显示出戏剧性的“碱色”配色转换,从而生成具有特征性电荷转移吸收的两性离子形式的染料。比色反应的程度随所测试的脂肪族胺(即丙胺,乙醇胺,乙二胺,二亚乙基三胺,三乙胺,三乙醇胺)的碱强度而变化,与p K b呈松散相关性。胺。此外,我们通过将发色探针溶解在离子液体1-丙基-1-甲基吡咯烷鎓双(三氟甲基磺酰基)酰亚胺中,证明了氨和脂肪胺的气相色谱检测的概念验证。我们还表明,染色的离子液体可以成功地固定在硅胶溶胶-凝胶离子凝胶中,以生成更实用,更坚固的感官平台。该策略代表了现有针对胺和其他碱性物质的比色传感器阵列的有用补充。特别地,两种不同探针的差异反应提供了一种化学选择性的度量,这对于检测食品安全性应用以及其他领域中的生物胺是有意义的。

更新日期:2018-06-27
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