Original scientific paper

https://doi.org/10.5562/cca2765

Synthesis and Anion Binding Properties of a Novel 1,8-dipyrrolecarbazole Schiff-base

Marina Šekutor ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, P.O. Box 180, 10 002, Zagreb, Croatia
Saša Opačak ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, P.O. Box 180, 10 002, Zagreb, Croatia
Marija Alešković ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, P.O. Box 180, 10 002, Zagreb, Croatia
Kata Mlinarić-Majerski orcid.org/0000-0001-6282-1662 ; Department of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, P.O. Box 180, 10 002, Zagreb, Croatia

Abstract

New anion receptor N1,N8-bis[1H-pyrro-2-yl-methylidene]-3,6-dichloro-9H-carbazole-1,8-diamine (3) was synthesized and its binding properties towards anions (Cl-, Br-, AcO- and H₂PO₄-) investigated by UV/Vis spectroscopy. In order to find the most stable structure of receptor 3, geometries of all possible isomers of 3 were optimized by the DFT/B3LYP method. It has been determined that receptor 3 forms complexes with a 1:1 stoichiometry with all the studied anions and no significant selectivity with respect to anion geometry was found. However, 1,8-dipyrrolecarbazole Schiff-base 3 binds oxoanions (H₂PO₄- and AcO-) more strongly than spherical halogenide (Cl- and Br-) anions.

Keywords

anion receptors; carbazole; pyrrole; Schiff-base

Hrčak ID:

151116

URI

https://hrcak.srce.hr/151116

Publication date:

31.12.2015.

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