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Diphenoquinhydrones and Related Hydrogen-Bonded Charge-Transfer Complexes
Sébastien Néron1, Mathieu Morency1, Cédric Malveau1
1Département de Chimie, Université de Montréal, Montréal, Québec H2V 0B3, Canada.
The Journal of Organic Chemistry
|November 10, 2022
Summary
Researchers created new diphenoquinhydrones by combining specific molecules. These materials exhibit strong intermolecular interactions, offering a modular approach to designing novel charge-transfer materials.
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Organic Chemistry
Background:
- Benzoquinone and hydroquinone form quinhydrone via hydrogen bonds and charge-transfer interactions.
- Quinhydrone's structure involves alternating components linked by non-covalent forces.
Purpose of the Study:
- To synthesize and characterize analogous diphenoquinhydrones.
- To explore the formation of mixed and mismatched quinhydrone structures.
- To investigate the intermolecular interactions and structural properties of these new complexes.
Main Methods:
- Cocrystallization of 4,4'-diphenoquinones with 4,4'-dihydroxybiphenyls.
- Assembly of mixed and mismatched quinhydrone systems.
- Analysis using geometric parameters, computational studies, and spectroscopic properties.
Main Results:
- Successful synthesis of analogous, mixed, and mismatched diphenoquinhydrones.
- Formation of planar chains linked by O-H···O hydrogen bonds.
- Layered structures with aligned π-donors and π-acceptors driven by charge-transfer interactions.
- Demonstrated stronger intermolecular interactions compared to simple quinhydrones.
Conclusions:
- The modular construction principles of quinhydrone formation are generalizable.
- A broad range of hydrogen-bonded charge-transfer materials can be designed.
- Diphenoquinhydrones represent a new class of tunable supramolecular materials.
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