Surface-Active Ionic Liquids and Surface-Active Quaternary Ammonium Salts from Synthesis, Characterization to Antimicrobial Properties

Author:

Wojcieszak Marta1,Kaczmarek Damian Krystian1ORCID,Karolak Maciej2ORCID,Pałkowski Łukasz2ORCID,Lewandowska Aneta1ORCID,Marcinkowska Agnieszka1ORCID,Dopierała Katarzyna1ORCID,Materna Katarzyna1ORCID

Affiliation:

1. Faculty of Chemical Technology, Poznan University of Technology, Berdychowo 4, PL-60965 Poznan, Poland

2. Department of Pharmaceutical Technology, Faculty of Pharmacy, Nicolaus Copernicus University, Jurasza 2, PL-85089 Bydgoszcz, Poland

Abstract

The present work provides new evidence of the ongoing potential of surface-active ionic liquids (SAILs) and surface-active quaternary ammonium salts (surface-active QASs). To achieve this, a series of compounds were synthesized with a yield of ≥85%, and their thermal analyses were studied. Additionally, antimicrobial activity against both human pathogenic and soil microorganisms was investigated. Subsequently, their surface properties were explored with the aim of utilizing SAILs and surface-active QASs as alternatives to commercial amphiphilic compounds. Finally, we analyzed the wettability of the leaves’ surface of plants occurring in agricultural fields at different temperatures (from 5 to 25 °C) and the model plant membrane of leaves. Our results show that the synthesized compounds exhibit higher activity than their commercial analogues such as, i.e., didecyldimethylammonium chloride (DDAC) and dodecyltrimethylammonium bromide (C12TAB), for which the CMC values are 2 mM and 15 mM. The effectiveness of the antimicrobial properties of synthesized compounds relies on their hydrophobic nature accompanied by a cut-off effect. Moreover, the best wettability of the leaves’ surface was observed at 25 °C. Our research has yielded valuable insights into the potential effectiveness of SAILs and surface-active QASs as versatile compounds, offering a promising alternative to established antimicrobials and crop protection agents, all the while preserving substantial surface activity.

Funder

Ministry of Education and Science in Poland

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

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