Suit[3]ane

Xiao Yang Chen, Dengke Shen, Kang Cai, Yang Jiao, Huang Wu, Bo Song, Long Zhang, Yu Tan, Yu Wang, Yuanning Feng, Charlotte L. Stern, J. Fraser Stoddart*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Suitanes are a class of mechanically interlocked molecules (MIMs) that consist of two components: a body with limbs protruding outward and a suit that fits appropriately around it, so that there is no easy way for the suit to be removed from the body. Herein, we report the synthesis and characterization of a suit[3]ane, which contains a benzotrithiophene derivative (THBTT) with three protruding hexyl chains as the body and a 3-fold symmetric, extended pyridinium-based cage, namely, HexaCage6+, as the suit. Central to its realization is effective templation, provided by THBTT during cage formation, an observation that has been supported by the strong binding constant between benzotrithiophene (BTT) and the empty cage. The solid-state structure of the suit[3]ane reveals that the body is confined within the suit's cavity with its alkyl chains protruding outward through the orifices in the cage. Notably, such a seemingly unstable molecule, having three flexible alkyl chains as its only protruding limbs, does not dissociate after prolonged heating in CD3CN at 100 °C under pressure for 7 days. No evidence for guest exchange with the host was observed at this temperature in a 2:1 mixture of THBTT and HexaCage6+ in CD3CN. The results indicate that flexible protruding limbs are sufficient for a suit[3]ane to remain mechanically stable even at high temperatures in solution.

Original languageEnglish (US)
Pages (from-to)20152-20160
Number of pages9
JournalJournal of the American Chemical Society
Volume142
Issue number47
DOIs
StatePublished - Nov 25 2020

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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