Temperature-Dependent Left- and Right-Twisted Conformational Changes in 1:1 Host-Guest Systems: Theoretical Modeling and Chiroptical Simulations

15 July 2024, Version 3
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

An efficient strategy for applying to chiral materials is to design and synthesize host molecules with left- and right-twisted conformations and to control their twisted conformations. For this, a quantitative analysis is required to describe the chiroptical inversion, chiral transfer, and chiral recognition in the host-guest systems, which is generally performed using circular dichroism (CD) and/or proton nuclear magnetic resonance (1H-NMR) spectroscopies. However, the mass-balance model that considers the left- and right-twisted conformations has not yet been established. In this study, we derived novel equations based on the mass-balance model for the 1:1 host-guest systems. Then, we further applied them to analyze the 1:1 host-guest systems for the achiral calixarene-based capsule molecule, achiral dimeric zinc porphyrin tweezer molecule, and chiral pillar[5]arene with the chiral and/or achiral guest molecules by using the data obtained from the CD titration, variable temperature CD (VT-CD), and 1H-NMR experiments. The thermodynamic parameters, equilibrium constants, and molar CD in the 1:1 host-guest systems could be successfully determined by the theoretical analyses using the derived equations.

Keywords

chiral
host-guest
supramolecule
twist
helix
circular dichroism
binding constant
equilibrium constant
molecular recognition
non-covalent interactions
twisted conformations

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