Anion-directed self-assembly of a 2,6-bis(2-anilinoethynyl)pyridine bis(amide) scaffold

Blakely W. Tresca, Orion B. Berryman, Lev N. Zakharov, Darren W. Johnson, Michael M. Haley

Research output: Contribution to journalArticlepeer-review

Abstract

Bis(sulfonamide) receptors based on the 2,6-bis(2-anilinoethynyl)pyridine scaffold form persistent dimers with water and halides in solution and in the solid-state. The structurally related bis(amide) receptor derived from 3,5-dinitrobenzoyl chloride is a dimer in the solid-state with two HCl molecules directing the self-assembly. The 2+2 dimer, with a twisted 'S'-shaped backbone, is held together by six hydrogen bonds. Dissolution of the (H2+·Cl-)2 adduct in CHCl3 results, however, in a monomeric structure. DOSY and 1H NMR experiments were used to identify the dominance of monomer in solution for both 2 and H2+·Cl-. The 'OFF-ON' fluorescence response of 2,6-bis(2-anilinoethynyl)pyridine is retained with amide arms.

Original languageEnglish
Pages (from-to)37-44
Number of pages8
JournalSupramolecular Chemistry
Volume28
Issue number1-2
DOIs
StatePublished - Feb 1 2016

Keywords

  • DOSY
  • amide binding
  • anion binding
  • host-guest
  • self-assembly

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