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Open AccessArticle

Synthesis of Tris-pillar[5]arene and Its Association with Phenothiazine Dye: Colorimetric Recognition of Anions

Kazan Federal University, Kremlevskaya, 18 Kazan, Russia
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Academic Editor: Roman Dembinski
Molecules 2019, 24(9), 1807; https://doi.org/10.3390/molecules24091807
Received: 10 April 2019 / Revised: 29 April 2019 / Accepted: 8 May 2019 / Published: 10 May 2019
(This article belongs to the Section Organic Chemistry)
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Abstract

A multicyclophane with a core based on tris(2-aminoethyl)amine (TREN) linked by amide spacers to three fragments of pillar[5]arene was synthesized. The choice of the tris-amide core allowed the multicyclophane to bind to anion guests. The presence of three terminal pillar[5]arene units provides the possibility of effectively binding the colorimetric probe N-phenyl-3-(phenylimino)-3H-phenothiazin-7-amine (PhTz). It was established that the multicyclophane complexed PhTz in chloroform with a 1:1 stoichiometry (lgKa = 5.2 ± 0.1), absorbing at 650 nm. The proposed structure of the complex was confirmed by 1H-NMR spectroscopy: the amide group linking the pillar[5]arene to the TREN core forms a hydrogen bond with the PhTz imino-group while the pillararenes surround PhTz. It was established that the PhTz:tris-pillar[5]arene complex could be used as a colorimetric probe for fluoride, acetate, and dihydrogen phosphate anions due to the anion binding with proton donating amide groups which displaced the PhTz probe. Dye displacement resulted in a color change from blue to pink, lowering the absorption band at 650 nm and increasing that at 533 nm. View Full-Text
Keywords: pillar[5]arene; complex; phenothiazine; anion; multipillar[5]arene pillar[5]arene; complex; phenothiazine; anion; multipillar[5]arene
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Khadieva, A.; Gorbachuk, V.; Shurpik, D.; Stoikov, I. Synthesis of Tris-pillar[5]arene and Its Association with Phenothiazine Dye: Colorimetric Recognition of Anions. Molecules 2019, 24, 1807.

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