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Article

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)
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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MDPI and ACS Style

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. https://doi.org/10.3390/molecules24091807

AMA Style

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(9):1807. https://doi.org/10.3390/molecules24091807

Chicago/Turabian Style

Khadieva, Alena, Vladimir Gorbachuk, Dmitriy Shurpik, and Ivan Stoikov. 2019. "Synthesis of Tris-pillar[5]arene and Its Association with Phenothiazine Dye: Colorimetric Recognition of Anions" Molecules 24, no. 9: 1807. https://doi.org/10.3390/molecules24091807

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