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Anion binding by p-aminoazobenzene-derived aromatic amides: spectroscopic and electrochemical studies

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Abstract

The synthesis and complexing properties of p-aminoazobenzene-derived mono-, bis-, and trisamides were described. Ligands 3 and 4 bind anions, including fluorides, chlorides, bromides, acetates, benzoates, dihydrogen phosphates, hydrogen sulfates, and p-toluenesulfonates, in chloroform forming 1: 1 complexes. The highest value of stability constant was evaluated for the 4-F− complex (log K = 5.63 ± 0.21). On the basis of 1H NMR, and FTIR spectroscopy, the possible nature of the ligand–anion interactions was proposed. The E ⇆ Z isomerization process of tripodal amide 4 in chloroform was studied. The effect of anions on Z to E thermal back isomerization was investigated.

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Acknowledgments

The authors kindly acknowledge support from sources for science GUT Grants No. 031841 and 032406. The authors also thank Prof. Elżbieta Luboch and Prof. Jan F. Biernat for fruitful discussion, student Marta Hewelt for her experimental contribution and Koleta Majewska, MSc for technical support in the manuscript preparation. The authors thank the anonymous reviewers for their careful review, which helped to improve the quality of the above manuscript.

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  1. Department of Chemistry and Technology of Functional Materials, Faculty of Chemistry, Gdansk University of Technology, Narutowicza Street 11/12, 80-233, Gdańsk, Poland

    Natalia Łukasik & Ewa Wagner-Wysiecka

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  1. Natalia Łukasik
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  2. Ewa Wagner-Wysiecka
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Correspondence to Natalia Łukasik or Ewa Wagner-Wysiecka.

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Łukasik, N., Wagner-Wysiecka, E. Anion binding by p-aminoazobenzene-derived aromatic amides: spectroscopic and electrochemical studies. Photochem Photobiol Sci 16, 1570–1579 (2017). https://doi.org/10.1039/c7pp00245a

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