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Open AccessArticle

Solution and Solid State Studies of Urea Derivatives of DITIPIRAM Acting as Powerful Anion Receptors

Institute of Organic Chemistry Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
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Academic Editor: Borys Osmialowski
Molecules 2021, 26(6), 1788; https://doi.org/10.3390/molecules26061788
Received: 26 February 2021 / Revised: 18 March 2021 / Accepted: 19 March 2021 / Published: 22 March 2021
(This article belongs to the Special Issue Structural Changes in Supramolecular Complexes)
Herein, we present the synthesis and anion binding studies of a family of homologous molecular receptors 47 based on a DITIPIRAM (8-propyldithieno-[3,2-b:2′,3′-e]-pyridine-3,5-di-amine) platform decorated with various urea para-phenyl substituents (NO2, F, CF3, and Me). Solution, X-ray, and DFT studies reveal that the presented host–guest system offers a convergent array of four urea NH hydrogen bond donors to anions allowing the formation of remarkably stable complexes with carboxylates (acetate, benzoate) and chloride anions in solution, even in competitive solvent mixtures such as DMSO-d6/H2O 99.5/0.5 (v/v) and DMSO-d3/MeOH-d3 9:1 (v/v). The most effective derivatives among the series turned out to be receptors 5 and 6 containing electron-withdrawing F- and -CF3para-substituents, respectively. View Full-Text
Keywords: anion recognition; acyclic receptors; supramolecular chemistry; DITIPIRAM anion recognition; acyclic receptors; supramolecular chemistry; DITIPIRAM
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MDPI and ACS Style

Niedbała, P.; Dąbrowa, K.; Cholewiak-Janusz, A.; Jurczak, J. Solution and Solid State Studies of Urea Derivatives of DITIPIRAM Acting as Powerful Anion Receptors. Molecules 2021, 26, 1788. https://doi.org/10.3390/molecules26061788

AMA Style

Niedbała P, Dąbrowa K, Cholewiak-Janusz A, Jurczak J. Solution and Solid State Studies of Urea Derivatives of DITIPIRAM Acting as Powerful Anion Receptors. Molecules. 2021; 26(6):1788. https://doi.org/10.3390/molecules26061788

Chicago/Turabian Style

Niedbała, Patryk; Dąbrowa, Kajetan; Cholewiak-Janusz, Agnieszka; Jurczak, Janusz. 2021. "Solution and Solid State Studies of Urea Derivatives of DITIPIRAM Acting as Powerful Anion Receptors" Molecules 26, no. 6: 1788. https://doi.org/10.3390/molecules26061788

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