Anion-directed self-assembly of a 2,6-bis(2-anilinoethynyl)pyridine bis(amide) scaffold.
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-)2adduct in CHCl3results, however, in a monomeric structure. DOSY and1H NMR experiments were used to identify the dominance of monomer in solution for both2andH2+·Cl-. The 'OFF-ON' fluorescence response of 2, 6-bis(2-anilinoethynyl)pyridine is retained with amide arms.
Department of Chemistry & Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, USA.
Blakely W
BW
Tresca
Department of Chemistry & Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, USA.
Orion B
OB
Berryman
CAMCOR, University of Oregon, 1443 East 13th Avenue, Eugene, Oregon 97403, USA.
Lev N
LN
Zakharov
Department of Chemistry & Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, USA.
Darren W
DW
Johnson
Department of Chemistry & Biochemistry and the Materials Science Institute, University of Oregon, Eugene, Oregon 97403-1253, USA.
Michael M
MM
Haley
DOSY; amide binding; anion binding; host-guest; self-assembly