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Pillarurilarenes: Glycoluril-Expanded Pillararenes.
Chao Ruan1,2, Zhijin Li1, Wenhao Lin1
1Key Laboratory of Mesoscopic Chemistry of MOE, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
Organic Letters
|May 2, 2024
Summary
New pillarurilarenes (PURA) were synthesized by incorporating glycoluril units into pillararene structures. This modification introduces polarized protons, enabling further chemical reactions and anion binding applications.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Macrocyclic Chemistry
Background:
- Pillararenes are a class of macrocyclic hosts with a tunable cavity.
- Expanding pillararene structures with different units can alter their properties and functionalities.
- Glycoluril units offer unique electronic and binding characteristics.
Purpose of the Study:
- To synthesize novel glycoluril-expanded pillararenes, termed pillarurilarenes (PURA).
- To investigate the structural and electronic properties of PURA, focusing on the impact of glycoluril incorporation.
- To explore the potential of PURA for derivatization and CH-anion binding.
Main Methods:
- Fragment coupling macrocyclization strategy for PURA synthesis.
- Single-crystal X-ray diffraction for structural elucidation of pillar[2]uril[4]arene and pillar[1]uril[4]arene.
- 1H nuclear magnetic resonance (NMR) spectroscopy and density functional theory (DFT) calculations to analyze structural and electronic properties.
Main Results:
- Successful synthesis of pillarurilarenes (PURA) incorporating glycoluril and dialkoxybenzene units.
- PURA exhibits polarized equatorial methine protons, facilitating derivatization and CH-anion binding.
- Structural analysis revealed an inward orientation of the glycoluril units within the macrocycle.
Conclusions:
- Glycoluril expansion provides a new avenue for modifying pillararene frameworks.
- The unique properties of PURA open possibilities for advanced host-guest chemistry and materials science.
- This research establishes a foundation for incorporating non-aromatic rings into pillararene structures.
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