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Origami with small molecules: exploiting the C-F bond as a conformational tool
Patrick Ryan1, Ramsha Iftikhar1, Luke Hunter1
1School of Chemistry, The University of New South Wales (UNSW), Sydney 2052, Australia.
Beilstein Journal of Organic Chemistry
|April 8, 2025
Summary
Fluorine's C-F bond influences molecular shape through stereoelectronic effects. This review covers 2010-2024 developments in using these effects to enhance functional molecules like pharmaceuticals and liquid crystals.
Area of Science:
- Organic Chemistry
- Molecular Conformation
- Fluorine Chemistry
Background:
- The carbon-fluorine (C-F) bond exhibits predictable alignment with neighboring functional groups.
- Stereoelectronic effects, including hyperconjugation and electrostatic interactions, drive these conformational preferences.
Purpose of the Study:
- To review the advancements in exploiting fluorine-derived conformational effects.
- To highlight the impact of these effects on molecular properties and applications from 2010-2024.
Main Methods:
- Literature review of scientific publications from 2010-2024.
- Analysis of studies demonstrating the application of C-F bond conformational control.
Main Results:
- Fluorine's influence on molecular conformation is a key factor in designing functional molecules.
- These effects have been successfully applied to optimize pharmaceuticals, liquid crystals, fragrances, organocatalysts, and peptides.
Conclusions:
- Stereoelectronic effects of the C-F bond offer a powerful tool for molecular engineering.
- Continued research in this area promises further innovation in materials science and drug discovery.
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