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Updated: Jun 1, 2026

Synthesis and Characterization of Functionalized Metal-organic Frameworks
Published on: September 5, 2014
Monofunctionalized pillar[5]arenes: synthesis and supramolecular structure
Tomoki Ogoshi1, Kazuki Demachi, Keisuke Kitajima
1Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. ogoshi@t.kanazawa-u.ac.jp
Researchers achieved the first synthesis of monohydroxy pillar[5]arene via controlled de-O-methylation. This intermediate enabled the creation of mono-guest-functionalized pillar[5]arene, forming self-inclusion complexes or undergoing guest dethreading depending on the solvent.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
Background:
- Pillar[5]arenes are macrocyclic compounds with unique host-guest properties.
- Selective functionalization of pillararenes is crucial for developing advanced supramolecular materials.
Purpose of the Study:
- To report the first synthesis of monohydroxy pillar[5]arene.
- To utilize this intermediate for preparing mono-guest-functionalized pillar[5]arene derivatives.
- To investigate the self-inclusion complexation behavior of these derivatives in different solvents.
Main Methods:
- Controlled de-O-methylation of per-methylated pillar[5]arene.
- Synthesis of mono-guest-functionalized pillar[5]arene using the monohydroxy intermediate.
- NMR spectroscopy to analyze complex formation and guest release in CDCl(3) and acetone-d(6).
Main Results:
- Successful synthesis of monohydroxy pillar[5]arene.
- Preparation of mono-guest-functionalized pillar[5]arene.
- Formation of a self-inclusion complex in CDCl(3).
- Dethreading of the guest moiety in acetone-d(6).
Conclusions:
- Monohydroxy pillar[5]arene is a viable intermediate for selective functionalization.
- The solvent-dependent behavior of mono-guest-functionalized pillar[5]arene highlights tunable supramolecular interactions.
- This work provides a pathway for designing sophisticated pillararene-based host-guest systems.
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