TY - JOUR A1 - Terao, Jun A1 - Konoshima, Yohei A1 - Matono, Akitoshi A1 - Masai, Hiroshi A1 - Fujihara, Tetsuaki A1 - Tsuji, Yasushi T1 - Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin JF - Beilstein Journal of Organic Chemistry PY - 2014/// VL - 10 SP - 2800 EP - 2808 SN - 1860-5397 DO - 10.3762/bjoc.10.297 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.10.297 KW - cross-coupling reaction KW - insulated π-conjugated molecule KW - oligothiophene KW - permethylated cyclodextrin KW - [3]rotaxane N2 - 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. ER -