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Triptycene-Derived Macrocyclic Arenes: From Calixarenes to Helicarenes
Chuan-Feng Chen1,2, Ying Han1
1Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function , Institute of Chemistry, Chinese Academy of Sciences , Beijing 100190 , China.
Accounts of Chemical Research
|August 24, 2018
Summary
Researchers developed novel triptycene-derived macrocyclic arenes, including helicarenes, offering fixed conformations and tunable complexation for molecular recognition and supramolecular chemistry applications.
Area of Science:
- Macrocyclic and Supramolecular Chemistry
- Organic Synthesis
- Host-Guest Chemistry
Background:
- Macrocyclic hosts are crucial in supramolecular chemistry, with calixarenes and their analogues being extensively studied.
- Triptycene derivatives offer unique 3D rigid structures, making them promising building blocks for novel macrocyclic hosts.
- Previous research has explored triptycene-based macrocycles, but new structures with enhanced properties are continuously sought.
Purpose of the Study:
- To synthesize and characterize novel triptycene-derived macrocyclic arenes and analogues.
- To investigate the structural features, conformational properties, and host-guest complexation abilities of these new macrocycles.
- To explore the potential applications of these triptycene-based macrocycles in molecular recognition, self-assembly, and the construction of interlocked molecules.
Main Methods:
- Synthesis of triptycene-derived macrocyclic arenes using dihydroxy-substituted triptycene precursors (1,8- and 2,7-dihydroxy).
- Characterization of synthesized compounds, including structural elucidation and conformational analysis in solution.
- Investigation of host-guest complexation using various chiral and achiral organic guests, and exploration of stimuli-responsive complexation.
Main Results:
- Successfully synthesized various triptycene-derived calixarene, oxacalixarene, homooxacalixarene analogues, and novel chiral helicarenes.
- These triptycene-based macrocycles exhibit fixed conformations, expanded cavities, and tunable complexation properties.
- Helicarenes demonstrate switchable complexation controlled by multiple stimuli (acid/base, redox, anion, light) and are effective in forming oriented [2]rotaxanes.
Conclusions:
- Triptycene-derived macrocyclic arenes, particularly helicarenes, represent a new class of synthetic hosts with significant potential.
- Their unique structural rigidity, tunable properties, and stimuli-responsive complexation enable advanced applications in supramolecular chemistry.
- These macrocycles are promising for molecular recognition, self-assembly, and the development of molecular machines and interlocked structures.
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