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Dynamic donor-acceptor [2]catenanes.

ABSTRACT: Donor-acceptor [2]catenanes based on cyclobis(paraquat-p-phenylene) as the pi-acceptor ring have been used prominently in the construction of functional molecular devices. We report here their thermodynamically controlled synthesis from isolated pi-donor and pi-acceptor rings under the catalytic influence of tetra butylammonium iodide. The initial nucleophilic attack of iodide ion, which opens up the pi-acceptor ring, is followed by complexation to the pi-donor ring and the subsequent catenation of the pi-donor ring by the pi-acceptor ring [2]catenane. The reaction is general in scope and proceeds in high yields, without giving rise to side-products.

SUBMITTER: Miljanic OS

PROVIDER: S-EPMC1941822 | biostudies-other | 2007 Aug

REPOSITORIES: biostudies-other

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Dynamic donor-acceptor [2]catenanes.

Miljanic Ognjen S OS Stoddart J Fraser JF

Proceedings of the National Academy of Sciences of the United States of America 20070801 32

Donor-acceptor [2]catenanes based on cyclobis(paraquat-p-phenylene) as the pi-acceptor ring have been used prominently in the construction of functional molecular devices. We report here their thermodynamically controlled synthesis from isolated pi-donor and pi-acceptor rings under the catalytic influence of tetra butylammonium iodide. The initial nucleophilic attack of iodide ion, which opens up the pi-acceptor ring, is followed by complexation to the pi-donor ring and the subsequent catenation ...[more]

PMID: 17670941

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