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

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.

SUBMITTER: Tresca BW

PROVIDER: S-EPMC4838391 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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

Tresca Blakely W BW Berryman Orion B OB Zakharov Lev N LN Johnson Darren W DW Haley Michael M MM

Supramolecular chemistry 20160129 1-2

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 adduc ...[more]

PMID: 27110083

Similar Datasets

Molecular Self Assembly: Solvent Guests Tune the Conformation of a Series of 2,6-Bis(2-anilinoethynyl)pyridine-Based Ureas.

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