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

Autor: Jun Terao, Yohei Konoshima, Akitoshi Matono, Hiroshi Masai, Tetsuaki Fujihara, Yasushi Tsuji
Jazyk: angličtina
Rok vydání: 2014
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 10, Iss 1, Pp 2800-2808 (2014)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.10.297
Popis: 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 derivatives were used as π-conjugated guests with stopper groups.
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