Supramolecular Conformational Control of Aliphatic Oligoketones by Rotaxane Formation

• Manabe, Yumehiro

• Wada, Keisuke

• Baba, Yudai

• Yoneda, Tomoki

• Ogoshi, Tomoki

• Inokuma, Yasuhide

Abstract

Conformational control of aliphatic oligoketones bearing two 1,3-diketone subunits is achieved by molecular recognition with pillar[5]arene. Pillar[S]arene binds to aliphatic ketones, with association constants K of similar to 10 M-1, to form pseudorotaxanes. The pseudorotaxanes are locked by BF, complexation at the 1,3-diketone sites through quasi-solid-state reactions. X-ray crystallography reveals linear conformations for the axis molecules. The effect of supramolecular conformational restriction is evaluated using an alkyl-linked dyad chromophore system that shows solvatochromism upon intramolecular aggregation.

Journal

• Organic letters

  Organic letters 22 (8), 3224-3228, 2020-04-17

  American Chemical Society

Keywords

• Equilibrium constant
• Supramolecular chemistry
• Chromophores
• Rotaxanes
• Conformation

Details

• CRID: 1050006352496220416
• NII Article ID: 120007026930
• DOI: 10.1021/acs.orglett.0c01010
• ISSN: 15237052
• ISSN: 15237060
• HANDLE: 2115/81007
• Web Site: https://pubs.acs.org/doi/pdf/10.1021/acs.orglett.0c01010
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN