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

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 succeed...

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Detalles Bibliográficos
Autores principales: Terao, Jun, Konoshima, Yohei, Matono, Akitoshi, Masai, Hiroshi, Fujihara, Tetsuaki, Tsuji, Yasushi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4273295/
https://www.ncbi.nlm.nih.gov/pubmed/25550746
http://dx.doi.org/10.3762/bjoc.10.297
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author Terao, Jun
Konoshima, Yohei
Matono, Akitoshi
Masai, Hiroshi
Fujihara, Tetsuaki
Tsuji, Yasushi
author_facet Terao, Jun
Konoshima, Yohei
Matono, Akitoshi
Masai, Hiroshi
Fujihara, Tetsuaki
Tsuji, Yasushi
author_sort Terao, Jun
collection PubMed
description 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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spelling pubmed-42732952014-12-30 Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin Terao, Jun Konoshima, Yohei Matono, Akitoshi Masai, Hiroshi Fujihara, Tetsuaki Tsuji, Yasushi Beilstein J Org Chem Letter 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. Beilstein-Institut 2014-11-28 /pmc/articles/PMC4273295/ /pubmed/25550746 http://dx.doi.org/10.3762/bjoc.10.297 Text en Copyright © 2014, Terao et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Terao, Jun
Konoshima, Yohei
Matono, Akitoshi
Masai, Hiroshi
Fujihara, Tetsuaki
Tsuji, Yasushi
Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin
title Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin
title_full Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin
title_fullStr Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin
title_full_unstemmed Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin
title_short Synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin
title_sort synthesis of an organic-soluble π-conjugated [3]rotaxane via rotation of glucopyranose units in permethylated β-cyclodextrin
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4273295/
https://www.ncbi.nlm.nih.gov/pubmed/25550746
http://dx.doi.org/10.3762/bjoc.10.297
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