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Ultra-fast One-Handed Helix Induction and Its Static Helicity Memory in a Poly(biphenylylacetylene) with a Catalytic Amount of Chiral Ammonium Salts.
Fukuda, Mayu; Morikawa, Mai; Hirose, Daisuke; Taniguchi, Tsuyoshi; Nishimura, Tatsuya; Yashima, Eiji; Maeda, Katsuhiro.
Affiliation
  • Fukuda M; Graduate School of Frontier Science Initiative, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan.
  • Morikawa M; Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan.
  • Hirose D; Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan.
  • Taniguchi T; Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan.
  • Nishimura T; Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan.
  • Yashima E; Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya, 464-8603, Japan.
  • Maeda K; Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan.
Angew Chem Int Ed Engl ; 62(15): e202217020, 2023 Apr 03.
Article in En | MEDLINE | ID: mdl-36718497
We report an ultra-fast helix induction and subsequent static helicity memory in poly(biphenylylacetylene) (PBPA-A) assisted by a catalytic amount of nonracemic ammonium salts comprised of non-coordinating tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (BArF- ) as a counter anion. The remarkable acceleration of the helix-induction rate in PBPA-A accompanied by the significant amplification of the asymmetry relies on the two methoxymethoxy groups of the biphenyl pendants, which can gain access to enfold the chiral ammoniums in a crown-ether manner in specific aromatic solvents, leading to ultra-fast helicity induction, which is completed within 30 s. In aromatic solvents, helicity memory is lost rapidly, but is quite stable in long-chain hydrocarbons. The best use of specific solvents for helicity induction and static helicity memory, respectively, provides a highly sensitive chirality sensing system toward a small amount of chiral amines and amino acids when complexed with BArF- .
Key words

Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Angew Chem Int Ed Engl Year: 2023 Document type: Article Affiliation country: Japan Country of publication: Germany

Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Angew Chem Int Ed Engl Year: 2023 Document type: Article Affiliation country: Japan Country of publication: Germany