Molecular tweezers with a rotationally restricted linker and freely rotating porphyrin moieties

Rhys B. Murphy, Duc-Truc Pham, Jonathan M. White, Stephen F. Lincoln, Martin R. Johnston

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

The effect of the degree of conformational rigidity and/or flexibility on preorganisation in artificial molecular receptors continues to be actively explored by supramolecular chemists. This work describes a bis-porphyrin architecture, linked via a rigid polycyclic backbone, in which a sterically bulky 2,3,5,6-tetramethylphenyl diimide core restricts rotation to afford two non-interconvertible tweezer conformations; syn- and anti-. After separation, the host-guest chemistry of each conformation was studied independently. The difference in host geometry allows only the syn-conformation to form a strong 1 : 1 bis-porphyrin complex with the diamino ligand 1,4-diazabicyclo[2.2.2]octane (DABCO) (K11 = 1.25 × 108 M-1), with the anti-conformation adopting a 2 : 2 sandwich complex with DABCO (K22 = 5.57 × 1017 M-3).

Original languageEnglish
Pages (from-to)6206-6223
Number of pages18
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number34
DOIs
Publication statusPublished - 14 Sep 2018

Keywords

  • Molecular tweezers
  • porphyrin moieties
  • artificial molecular receptors
  • conformational rigidity
  • conformational flexibility

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