Triple Helicene Cage: Three‐Dimensional π‐Conjugated Chiral Cage with Six [5]Helicene Units

A three‐dimensional π‐conjugated chiral cage with six [5]helicene units (a triple helicene cage) was synthesized for the first time. Taking advantage of the Yamamoto coupling reaction, the triflate‐substituted triple [5]helicene, a strained and preorganized precursor, was dimerized to afford the tar...

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Autores principales: Matsushima, Tomoya, Kikkawa, Shoko, Azumaya, Isao, Watanabe, Soichiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5891663/
https://www.ncbi.nlm.nih.gov/pubmed/29657913
http://dx.doi.org/10.1002/open.201800006
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author Matsushima, Tomoya
Kikkawa, Shoko
Azumaya, Isao
Watanabe, Soichiro
author_facet Matsushima, Tomoya
Kikkawa, Shoko
Azumaya, Isao
Watanabe, Soichiro
author_sort Matsushima, Tomoya
collection PubMed
description A three‐dimensional π‐conjugated chiral cage with six [5]helicene units (a triple helicene cage) was synthesized for the first time. Taking advantage of the Yamamoto coupling reaction, the triflate‐substituted triple [5]helicene, a strained and preorganized precursor, was dimerized to afford the target compound. Single‐crystal X‐ray diffraction analysis revealed the unique structural features of the triple helicene cage: a cage‐shaped rigid structure with outer helical grooves and an inner chiral cavity. All‐P and all‐M enantiomers were separated successfully by HPLC over a chiral column and their chiroptical properties were characterized by circular dichroism spectra.
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spelling pubmed-58916632018-04-13 Triple Helicene Cage: Three‐Dimensional π‐Conjugated Chiral Cage with Six [5]Helicene Units Matsushima, Tomoya Kikkawa, Shoko Azumaya, Isao Watanabe, Soichiro ChemistryOpen Communications A three‐dimensional π‐conjugated chiral cage with six [5]helicene units (a triple helicene cage) was synthesized for the first time. Taking advantage of the Yamamoto coupling reaction, the triflate‐substituted triple [5]helicene, a strained and preorganized precursor, was dimerized to afford the target compound. Single‐crystal X‐ray diffraction analysis revealed the unique structural features of the triple helicene cage: a cage‐shaped rigid structure with outer helical grooves and an inner chiral cavity. All‐P and all‐M enantiomers were separated successfully by HPLC over a chiral column and their chiroptical properties were characterized by circular dichroism spectra. John Wiley and Sons Inc. 2018-02-16 /pmc/articles/PMC5891663/ /pubmed/29657913 http://dx.doi.org/10.1002/open.201800006 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Matsushima, Tomoya
Kikkawa, Shoko
Azumaya, Isao
Watanabe, Soichiro
Triple Helicene Cage: Three‐Dimensional π‐Conjugated Chiral Cage with Six [5]Helicene Units
title Triple Helicene Cage: Three‐Dimensional π‐Conjugated Chiral Cage with Six [5]Helicene Units
title_full Triple Helicene Cage: Three‐Dimensional π‐Conjugated Chiral Cage with Six [5]Helicene Units
title_fullStr Triple Helicene Cage: Three‐Dimensional π‐Conjugated Chiral Cage with Six [5]Helicene Units
title_full_unstemmed Triple Helicene Cage: Three‐Dimensional π‐Conjugated Chiral Cage with Six [5]Helicene Units
title_short Triple Helicene Cage: Three‐Dimensional π‐Conjugated Chiral Cage with Six [5]Helicene Units
title_sort triple helicene cage: three‐dimensional π‐conjugated chiral cage with six [5]helicene units
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5891663/
https://www.ncbi.nlm.nih.gov/pubmed/29657913
http://dx.doi.org/10.1002/open.201800006
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AT azumayaisao triplehelicenecagethreedimensionalpconjugatedchiralcagewithsix5heliceneunits
AT watanabesoichiro triplehelicenecagethreedimensionalpconjugatedchiralcagewithsix5heliceneunits

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