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Synthesis of an organic-soluble ?-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated ?-cyclodextrin.

ABSTRACT: We synthesized symmetrically insulated oligo(para-phenylene) and oligothiophene with a pseudo-linked [3]rotaxane structure by full rotation of glucopyranose units via a flipping (tumbling) mechanism in the ?-conjugated guest having two permethylated ?-cyclodextrin units at both ends. We also succeeded in the synthesis of an organic-soluble fixed [3]rotaxane by a cross-coupling or complexation reaction of thus formed pseudo linked [3]rotaxane. Oligo(para-phenylene), oligothiophene, and porphyrin derivatives were used as ?-conjugated guests with stopper groups.

SUBMITTER: Terao J

PROVIDER: S-EPMC4273295 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

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Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin.

Terao Jun J Konoshima Yohei Y Matono Akitoshi A Masai Hiroshi H Fujihara Tetsuaki T Tsuji Yasushi Y

Beilstein journal of organic chemistry 20141128

We synthesized symmetrically insulated oligo(para-phenylene) and oligothiophene with a pseudo-linked [3]rotaxane structure by full rotation of glucopyranose units via a flipping (tumbling) mechanism in the π-conjugated guest having two permethylated β-cyclodextrin units at both ends. We also succeeded in the synthesis of an organic-soluble fixed [3]rotaxane by a cross-coupling or complexation reaction of thus formed pseudo linked [3]rotaxane. Oligo(para-phenylene), oligothiophene, and porphyrin ...[more]

PMID: 25550746

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