Abstract
In the present work, new host-guest binding motifs based on a water-soluble pillar[6]arene dodecyl-ammonium chloride (CP6) with two aromatic sulfonic acids in aqueous media were fabricated. In accordance with the integrated results of 1H NMR, 2D NOESY, and florescence titration experiments, it was demonstrated that the host-guest binding of CP6 with the two aromatic sulfonic acids in aqueous solution not only has high binding constants but also has pH-responsiveness.
Highlights
In the supramolecular chemistry field, stimuli-responsive molecular host-guest recognition motifs are attracting much attention because of their wide range of applications in the fabrication of various fascinating and important supramolecular systems, such as molecular devices and machines (Palmer and Rebek, 2004; Han and Chen, 2007; Zhang et al, 2014), responsive supramolecular polymers (Xu et al, 2013; Cantekin et al, 2015), and other smart supramolecular materials (Avestro et al, 2012; Guo and Liu, 2012; Li et al, 2012; Vukotic and Loeb, 2012)
We show that CP6 can form highly stable host-guest complexes with p-TSA and 2-naphthalenesulfonic acid (2-NA), respectively
Novel pH-responsive host-guest recognition motifs based on a water-soluble pillar[6]arene dodecyl-ammonium chloride CP6 with p-TSA or 2-NA were successfully constructed
Summary
In the supramolecular chemistry field, stimuli-responsive molecular host-guest recognition motifs are attracting much attention because of their wide range of applications in the fabrication of various fascinating and important supramolecular systems, such as molecular devices and machines (Palmer and Rebek, 2004; Han and Chen, 2007; Zhang et al, 2014), responsive supramolecular polymers (Xu et al, 2013; Cantekin et al, 2015), and other smart supramolecular materials (Avestro et al, 2012; Guo and Liu, 2012; Li et al, 2012; Vukotic and Loeb, 2012). Pillararenes (Ogoshi et al, 2008, 2016; Cao et al, 2009, 2014; Xue et al, 2012; Yao et al, 2012; Si et al, 2014; Wang et al, 2019), as a new kind of supramolecular macrocyclic hosts, have gained growing attention due to their intrinsic unique rigid and symmetrical pillar-shaped architecture, tunable cavity size, easy modification, and superior host-guest properties Pillararenes endowed with these outstanding features have been used to construct numerous supramolecular systems, such as supramolecular polymers (Zhang et al, 2011; Guan et al, 2012; Li, 2014), daisy chains (Zhang et al, 2012), transmembrane channels (Si et al, 2014), drug-release systems (Cao et al, 2014; Chang et al, 2014; Hu et al, 2016), and other advanced functional materials (Ni et al, 2016; Wang et al, 2018; Xiao et al, 2018; Zhou et al, 2020). A series of water-soluble pillararenes pH-Responsive Pillararenes Complexes
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