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Updated: Jul 31, 2026
09:35
Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Interactions at the outside faces of calix
Messina1, Metrangolo, Pappalardo
1Dipartimento di Chimica, Politecnico di Milano, Italy.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 10, 2000
Summary
Researchers created novel 1D non-covalent ribbons and 2D supramolecular networks using calixarene and perfluoroarene building blocks. These structures self-assemble through pi-pi and halogen bonding interactions, forming intricate molecular architectures.
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Organic Chemistry
Background:
- Calixarenes are versatile macrocyclic hosts with tunable properties.
- Perfluoroarenes are electron-deficient aromatic compounds with unique reactivity.
- Non-covalent interactions are crucial for constructing complex molecular assemblies.
Purpose of the Study:
- To investigate the self-assembly of 1,3-bis-pyridylmethylcalix[4]arene with halogenated perfluoroarenes.
- To explore the formation of 1D ribbons and 2D networks driven by pi-pi and halogen bonding.
- To establish a new binding protocol for calixarene self-assembly.
Main Methods:
- Synthesis of 1,3-bis-pyridylmethylcalix[4]arene.
- Co-crystallization with 1,4-diiodotetrafluorobenzene and 1,4-dibromotetrafluorobenzene.
- Single-crystal X-ray diffraction analysis.
Main Results:
- Formation of infinite 1D non-covalent ribbons through alternating pi-pi interactions between calixarene and perfluoroarene modules.
- Cross-linking of ribbons via electron donor-acceptor interactions, leading to 2D supramolecular networks.
- Orthogonal arrangement of pi-pi and halogen bonding interactions, with diiodotetrafluorobenzene acting as a key tecton.
Conclusions:
- Attractive pi-pi and halogen bonding interactions effectively direct the self-assembly of calixarene and perfluoroarene systems.
- The identified interactions provide a general and effective binding protocol for calixarene-based supramolecular construction.
- Electron-poor arenes can elicit exo-receptor potential in calixarenes, enabling novel self-assembly strategies.
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