Dynamic donor–acceptor [2]catenanes
- 7 August 2007
- journal article
- research article
- Published by Proceedings of the National Academy of Sciences in Proceedings of the National Academy of Sciences
- Vol. 104 (32), 12966-12970
- https://doi.org/10.1073/pnas.0704136104
Abstract
Donor–acceptor [2]catenanes based on cyclobis(paraquat-p-phenylene) as the π-acceptor ring have been used prominently in the construction of functional molecular devices. We report here their thermodynamically controlled synthesis from isolated π-donor and π-acceptor rings under the catalytic influence of tetra butylammonium iodide. The initial nucleophilic attack of iodide ion, which opens up the π-acceptor ring, is followed by complexation to the π-donor ring and the subsequent catenation of the π-donor ring by the π-acceptor ring [2]catenane. The reaction is general in scope and proceeds in high yields, without giving rise to side-products.Keywords
This publication has 31 references indexed in Scilit:
- Toward Electrochemically Controllable Tristable Three‐Station [2]CatenanesChemistry – An Asian Journal, 2006
- Single‐Walled Carbon Nanotube Based Molecular Switch Tunnel JunctionsChemphyschem, 2003
- A Chemically and Electrochemically Switchable [2]Catenane Incorporating a Tetrathiafulvalene UnitAngewandte Chemie International Edition, 1998
- Reversible synthesis of π-associated [2]catenanes by ring-closing metathesis: towards dynamic combinatorial libraries of catenanesNew Journal of Chemistry, 1998
- High‐Yield Synthesis of [2] Catenanes by Intramolecular Ring‐Closing MetathesisAngewandte Chemie International Edition in English, 1997
- Recognition of Bipyridinium-Based Derivatives by Hydroquinone- and/or Dioxynaphthalene-Based Macrocyclic Polyethers: From Inclusion Complexes to the Self-Assembly of [2]CatenanesThe Journal of Organic Chemistry, 1997
- Controlling Translational Isomerism in [2]CatenanesAngewandte Chemie International Edition in English, 1995
- A chemically and electrochemically switchable molecular shuttleNature, 1994
- A [2] Catenane Made to OrderAngewandte Chemie International Edition in English, 1989
- Isostructural, Alternately‐Charged Receptor Stacks. The Inclusion Complexes of Hydroquinone and Catechol Dimethyl Ethers with Cyclobis(paraquat‐p‐phenylene)Angewandte Chemie International Edition in English, 1988