A conformationally adaptive macrocycle: conformational complexity and host-guest chemistry of zorb[4]arene

Beilstein Journal of Organic Chemistry
Liu-Pan YangWei Jiang

Abstract

Large amplitude conformational change is one of the features of biomolecular recognition and is also the basis for allosteric effects and signal transduction in functional biological systems. However, synthetic receptors with controllable conformational changes are rare. In this article, we present a thorough study on the host-guest chemistry of a conformationally adaptive macrocycle, namely per-O-ethoxyzorb[4]arene (ZB4). Similar to per-O-ethoxyoxatub[4]arene, ZB4 is capable of accommodating a wide range of organic cations. However, ZB4 does not show large amplitude conformational responses to the electronic substituents on the guests. Instead of a linear free-energy relationship, ZB4 follows a parabolic free-energy relationship. This is explained by invoking the influence of secondary C-H···O hydrogen bonds on the primary cation···π interactions based on the information obtained from four representative crystal structures. In addition, heat capacity changes (ΔCp) and enthalpy-entropy compensation phenomena both indicate that solvent reorganization is also involved during the binding. This research further deepens our understanding on the binding behavior of ZB4 and lays the basis for the construction of stimuli-responsive mat...Continue Reading

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Citations

Jun 19, 2019·Chemical Communications : Chem Comm·Hongxin ChaiWei Jiang
Jul 30, 2019·Beilstein Journal of Organic Chemistry·Li-Li WangWei Jiang
Dec 21, 2019·Chemical Communications : Chem Comm·Song-Bo LuWei Jiang
May 28, 2020·Chemical Society Reviews·Xiaoping WangWei Jiang

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Methods Mentioned

BETA
NMR
isothermal titration microcalorimetry
X-ray

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