Synthesis and physical properties of a ball-like three-dimensional π-conjugated molecule

Curved π-conjugated molecules with closed and three-dimensional (3D) structures, such as fullerenes and carbon nanotubes, have been the subject of intensive research due to their potential applications in molecular electronics. However, basic molecular skeletons of 3D molecules are limited because o...

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Published inNature communications Vol. 4; no. 1; p. 2694
Main Authors Kayahara, Eiichi, Iwamoto, Takahiro, Takaya, Hikaru, Suzuki, Toshiyasu, Fujitsuka, Mamoru, Majima, Tetsuro, Yasuda, Nobuhiro, Matsuyama, Naoto, Seki, Shu, Yamago, Shigeru
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 2013
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Online AccessGet full text
ISSN2041-1723
2041-1723
DOI10.1038/ncomms3694

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Abstract Curved π-conjugated molecules with closed and three-dimensional (3D) structures, such as fullerenes and carbon nanotubes, have been the subject of intensive research due to their potential applications in molecular electronics. However, basic molecular skeletons of 3D molecules are limited because of the lack of a rational and selective synthetic method by organic synthesis. Here we report the synthesis of a 3D π-conjugated molecule based on the platinum-mediated assembly of four molecules of a stannylated trisubstituted benzene derivative forming a hexanuclear platinum complex with an octahedral shape, from which reductive elimination of platinum gave the target molecule. As many supramolecular transition metal–ligand complexes with 3D cages and polyhedral structures have been synthesized by self-assembly of ligands and metals, the current assembly/reductive elimination strategy could provide a variety of new 3D π-conjugated molecules with different structures and topologies, which are challenging to obtain using conventional synthetic methods. Curved π-conjugated compounds, such as the fullerenes, have a variety of practical uses in addition to being structurally striking. Here, the authors demonstrate metal-mediated assembly and subsequent reductive elimination as an elegant synthetic route to a fully conjugated ball-like molecule.
AbstractList Curved π-conjugated molecules with closed and three-dimensional (3D) structures, such as fullerenes and carbon nanotubes, have been the subject of intensive research due to their potential applications in molecular electronics. However, basic molecular skeletons of 3D molecules are limited because of the lack of a rational and selective synthetic method by organic synthesis. Here we report the synthesis of a 3D π-conjugated molecule based on the platinum-mediated assembly of four molecules of a stannylated trisubstituted benzene derivative forming a hexanuclear platinum complex with an octahedral shape, from which reductive elimination of platinum gave the target molecule. As many supramolecular transition metal-ligand complexes with 3D cages and polyhedral structures have been synthesized by self-assembly of ligands and metals, the current assembly/reductive elimination strategy could provide a variety of new 3D π-conjugated molecules with different structures and topologies, which are challenging to obtain using conventional synthetic methods.
Curved π-conjugated molecules with closed and three-dimensional (3D) structures, such as fullerenes and carbon nanotubes, have been the subject of intensive research due to their potential applications in molecular electronics. However, basic molecular skeletons of 3D molecules are limited because of the lack of a rational and selective synthetic method by organic synthesis. Here we report the synthesis of a 3D π-conjugated molecule based on the platinum-mediated assembly of four molecules of a stannylated trisubstituted benzene derivative forming a hexanuclear platinum complex with an octahedral shape, from which reductive elimination of platinum gave the target molecule. As many supramolecular transition metal-ligand complexes with 3D cages and polyhedral structures have been synthesized by self-assembly of ligands and metals, the current assembly/reductive elimination strategy could provide a variety of new 3D π-conjugated molecules with different structures and topologies, which are challenging to obtain using conventional synthetic methods.Curved π-conjugated molecules with closed and three-dimensional (3D) structures, such as fullerenes and carbon nanotubes, have been the subject of intensive research due to their potential applications in molecular electronics. However, basic molecular skeletons of 3D molecules are limited because of the lack of a rational and selective synthetic method by organic synthesis. Here we report the synthesis of a 3D π-conjugated molecule based on the platinum-mediated assembly of four molecules of a stannylated trisubstituted benzene derivative forming a hexanuclear platinum complex with an octahedral shape, from which reductive elimination of platinum gave the target molecule. As many supramolecular transition metal-ligand complexes with 3D cages and polyhedral structures have been synthesized by self-assembly of ligands and metals, the current assembly/reductive elimination strategy could provide a variety of new 3D π-conjugated molecules with different structures and topologies, which are challenging to obtain using conventional synthetic methods.
Curved π-conjugated molecules with closed and three-dimensional (3D) structures, such as fullerenes and carbon nanotubes, have been the subject of intensive research due to their potential applications in molecular electronics. However, basic molecular skeletons of 3D molecules are limited because of the lack of a rational and selective synthetic method by organic synthesis. Here we report the synthesis of a 3D π-conjugated molecule based on the platinum-mediated assembly of four molecules of a stannylated trisubstituted benzene derivative forming a hexanuclear platinum complex with an octahedral shape, from which reductive elimination of platinum gave the target molecule. As many supramolecular transition metal–ligand complexes with 3D cages and polyhedral structures have been synthesized by self-assembly of ligands and metals, the current assembly/reductive elimination strategy could provide a variety of new 3D π-conjugated molecules with different structures and topologies, which are challenging to obtain using conventional synthetic methods. Curved π-conjugated compounds, such as the fullerenes, have a variety of practical uses in addition to being structurally striking. Here, the authors demonstrate metal-mediated assembly and subsequent reductive elimination as an elegant synthetic route to a fully conjugated ball-like molecule.
ArticleNumber 2694
Author Takaya, Hikaru
Suzuki, Toshiyasu
Fujitsuka, Mamoru
Matsuyama, Naoto
Iwamoto, Takahiro
Seki, Shu
Majima, Tetsuro
Kayahara, Eiichi
Yamago, Shigeru
Yasuda, Nobuhiro
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  organization: Institute for Chemical Research, Kyoto University, CREST, Japan Science and Technology Agency
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  surname: Iwamoto
  fullname: Iwamoto, Takahiro
  organization: Institute for Chemical Research, Kyoto University
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  givenname: Hikaru
  surname: Takaya
  fullname: Takaya, Hikaru
  organization: Institute for Chemical Research, Kyoto University
– sequence: 4
  givenname: Toshiyasu
  surname: Suzuki
  fullname: Suzuki, Toshiyasu
  organization: CREST, Japan Science and Technology Agency, Institute for Molecular Science, National Institute of Natural Sciences
– sequence: 5
  givenname: Mamoru
  surname: Fujitsuka
  fullname: Fujitsuka, Mamoru
  organization: CREST, Japan Science and Technology Agency, The Institute of Scientific and Industrial Research, Osaka University
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  givenname: Tetsuro
  surname: Majima
  fullname: Majima, Tetsuro
  organization: CREST, Japan Science and Technology Agency, The Institute of Scientific and Industrial Research, Osaka University
– sequence: 7
  givenname: Nobuhiro
  surname: Yasuda
  fullname: Yasuda, Nobuhiro
  organization: Research and Utilization Division, Japan Synchrotron Radiation Research Institute
– sequence: 8
  givenname: Naoto
  surname: Matsuyama
  fullname: Matsuyama, Naoto
  organization: Department of Applied Chemistry, Osaka University
– sequence: 9
  givenname: Shu
  surname: Seki
  fullname: Seki, Shu
  organization: Department of Applied Chemistry, Osaka University
– sequence: 10
  givenname: Shigeru
  surname: Yamago
  fullname: Yamago, Shigeru
  email: yamago@scl.kyoto-u.ac.jp
  organization: Institute for Chemical Research, Kyoto University, CREST, Japan Science and Technology Agency
BackLink https://www.ncbi.nlm.nih.gov/pubmed/24165515$$D View this record in MEDLINE/PubMed
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Snippet Curved π-conjugated molecules with closed and three-dimensional (3D) structures, such as fullerenes and carbon nanotubes, have been the subject of intensive...
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Title Synthesis and physical properties of a ball-like three-dimensional π-conjugated molecule
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