Squaramide-Based Self-Associating Amphiphiles for Anion Recognition.

Autor: Kumawat LK; Department of Chemistry, Maynooth University, National University of Ireland, Maynooth, Co. Kildare, Ireland., Wynne C; Department of Chemistry, Maynooth University, National University of Ireland, Maynooth, Co. Kildare, Ireland.; Synthesis and Solid State Pharmaceutical Centre (SSPC), Ireland., Cappello E; School of Chemistry, Trinity Biomedical Sciences Institute (TBSI), Trinity College Dublin, The University of Dublin, Dublin 2, Ireland., Fisher P; Department of Chemistry, Maynooth University, National University of Ireland, Maynooth, Co. Kildare, Ireland., Brennan LE; Department of Chemistry, Maynooth University, National University of Ireland, Maynooth, Co. Kildare, Ireland., Strofaldi A; Department of Chemistry, Maynooth University, National University of Ireland, Maynooth, Co. Kildare, Ireland., McManus JJ; Department of Chemistry, Maynooth University, National University of Ireland, Maynooth, Co. Kildare, Ireland.; HH Wills Physics Laboratory, University of Bristol, Tyndall Avenue, Bristol, BS8 1TL, United Kingdom.; Synthesis and Solid State Pharmaceutical Centre (SSPC), Ireland., Hawes CS; School of Chemical and Physical Sciences, Keele University, Keele, ST5 5BG, United Kingdom., Jolliffe KA; School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia., Gunnlaugsson T; School of Chemistry, Trinity Biomedical Sciences Institute (TBSI), Trinity College Dublin, The University of Dublin, Dublin 2, Ireland.; Synthesis and Solid State Pharmaceutical Centre (SSPC), Ireland., Elmes RBP; Department of Chemistry, Maynooth University, National University of Ireland, Maynooth, Co. Kildare, Ireland.; Kathleen Lonsdale Institute for Human Health Research, Maynooth University, Maynooth, Co. Kildare, Ireland.; Synthesis and Solid State Pharmaceutical Centre (SSPC), Ireland.
Jazyk: angličtina
Zdroj: ChemPlusChem [Chempluschem] 2021 Aug; Vol. 86 (8), pp. 1058-1068.
DOI: 10.1002/cplu.202100275
Abstrakt: The synthesis and characterisation of two novel self-assembled amphiphiles (SSAs) SQS-1 and SQS-2 are reported. Both compounds, based on the squaramide motif, were fully soluble in a range of solvents and were shown to undergo self-assembly through a range of physical techniques. Self-assembly was shown to favour the formation of crystalline domains on the nanoscale but also fibrillar film formation, as suggested by SEM analysis. Moreover, both SQS-1 and SQS-2 were capable of anion recognition in DMSO solution as demonstrated using 1 H NMR and UV/Vis absorption spectroscopy, but displayed lower binding affinities for various anions when compared against other squaramide based receptors. In more competitive solvent mixtures SQS-1 gave rise to a colourimetric response in the presence of HPO 4 2- that was clearly visible to the naked eye. We anticipate that the observed response is due to the basic nature of the HPO 4 2- anion when compared against other biologically relevant anions.
(© 2021 The Authors. ChemPlusChem published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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