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Research Article Section: Organic Chemistry

Efficient Control of the Formation of Pillar[5]arene-based Supramolecular Polymers

Author(s): Luzhi Liu*, Qin He, Qingqing Zhou, Xue Qin, Wenxue Zhang, Yan Huang* and Wengui Duan

Volume 2, Issue 2, 2022

Published on: 24 March, 2022

Page: [152 - 159] Pages: 8

DOI: 10.2174/2210298102666220315122623

Price: $65

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Abstract

Background: The design and preparation of functional pillar[n]arene-based supramolecular polymers have attracted extensive attention due to their wide range of applications.

Objective and Methods: Based on the synergistic effects of non-covalent interactions, including hydrogen bonds and host-guest interaction, an amphiphilic pillar[5]arene 1 with two terminated acid chains was designed, and its self-assembly properties were investigated by 1HNMR, TEM, SEM and UV-Vis.

Results: The pillar[5]arene 1 can form a self-inclusion complex, whose carboxyl groups are locked on the surface of the cavity at low concentration (<4.5 mM) in chloroform. Interestingly, when competitive guest dihaloalkanes, such as α,ω-diiodobutane (DIB), α,ω-dibromobutane (DBB) and α,ω-dichlorobutane (DCB), were added, supramolecular polymers were immediately obtained and precipitated. Their critical precipitation concentration (CPC) were calculated as 1 mM, 3 mM and 5 mM for DIB, DBB and DCB, respectively. Moreover, tuning the solvent, concentration and guests can reversibly control their polymerization.

Conclusion: This study provided an efficient method for the preparation of pillar[5]arene-based supramolecular polymers, which have the potential for the separation or purification of the dihaloalkanes.

Keywords: Pillar[5]arene, pseudo[2]rotaxane, supramolecular polymer, self-assembly, host-guest interaction, calculation.

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