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Published on: July 27, 2022

Molecular Recognition Process in Resorcinarene-based Coordination Capsules.

Kentaro Harada¹, Ryo Sekiya¹, Takeharu Haino^1,2

¹Department of Chemistry, Graduate School of Advanced Science and Engineering, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima, 739-8526, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|September 14, 2023

Summary

Copper and silver capsules recognize organic molecules through partial dissociation and slippage. This study reveals how these host-guest complexation mechanisms enable molecular uptake in specific capsule structures.

Keywords:

host-guest kinetics molecular recognition resorcinarene supramolecular chemistry

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Engineering Molecular Recognition with Bio-mimetic Polymers on Single Walled Carbon Nanotubes

Engineering Molecular Recognition with Bio-mimetic Polymers on Single Walled Carbon Nanotubes

Published on: January 10, 2017

Area of Science:

Supramolecular Chemistry
Coordination Chemistry

Background:

Metal-organic capsules, such as copper (Cu) and silver (Ag) capsules, exhibit the ability to encapsulate diverse organic molecules.
The precise mechanisms governing this molecular recognition, potentially involving partial dissociation and slippage of the capsule components, remain an area of active investigation.

Purpose of the Study:

To elucidate the molecular recognition processes in Cu and Ag capsules using a specific organic probe.
To investigate the roles of partial dissociation and slippage in host-guest complexation within these systems.

Main Methods:

Employed circular dichroism (CD) and proton nuclear magnetic resonance (¹H NMR) spectroscopy to study molecular recognition.
Utilized 4,4'-diacetoxy biphenyl with benzothiadiazole groups as a molecular probe for complexation studies.
Performed density functional theory (DFT) calculations to understand structural and electronic interactions.

Main Results:

Host-guest complexation was found to proceed via second-order reactions.
Partial dissociation of the capsules was observed to facilitate probe uptake in specific solvents (CDCl₃ and THF-d₈).
Slippage was identified as a key mechanism for guest inclusion in a Cu capsule functionalized with p-methoxyphenyl groups, aided by π/π stacking interactions.

Conclusions:

Both partial dissociation and slippage are crucial mechanisms for molecular recognition in Cu and Ag capsules.
The specific functionalization of the capsule, like the presence of p-methoxyphenyl groups, can influence the dominant complexation pathway.
DFT calculations support the role of non-covalent interactions in modulating capsule structure and guest accessibility.