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

Herein, we present the synthesis and anion binding studies of a family of homologous molecular receptors <b>4</b>–<b>7</b> based on a DITIPIRAM (8-propyldithieno-[3,2-b:2′,3′-e]-pyridine-3,5-di- amine) platform decorated with various urea <i>para</i>-phenyl substi...

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Bibliographic Details
Main Authors: Patryk Niedbała, Kajetan Dąbrowa, Agnieszka Cholewiak-Janusz, Janusz Jurczak
Format: Article
Language:English
Published: MDPI AG 2021-03-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/26/6/1788
Description
Summary:Herein, we present the synthesis and anion binding studies of a family of homologous molecular receptors <b>4</b>–<b>7</b> based on a DITIPIRAM (8-propyldithieno-[3,2-b:2′,3′-e]-pyridine-3,5-di- amine) platform decorated with various urea <i>para</i>-phenyl substituents (NO<sub>2</sub>, F, CF<sub>3</sub>, 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-<i>d</i><sub>6</sub>/H<sub>2</sub>O 99.5/0.5 (<i>v</i>/<i>v</i>) and DMSO-<i>d</i><sub>3</sub>/MeOH-<i>d</i><sub>3</sub> 9:1 (<i>v</i>/<i>v</i>). The most effective derivatives among the series turned out to be receptors <b>5</b> and <b>6</b> containing electron-withdrawing F- and -CF<sub>3</sub><i>para</i>-substituents, respectively.
ISSN:1420-3049