Exploiting Hydrogen Bonding to Direct Supramolecular Polymerization at the Air/Water Interface

Molecular tectonics. Use of the hydrogen bonding of boronic acids to direct supramolecular construction.

Tetraboronic acids 1 and 2 have four -B(OH)(2) groups oriented tetrahedrally by cores derived from tetraphenylmethane and tetraphenylsilane. Crystallization produces isostructural diamondoid networks held together by hydrogen bonding of the -B(OH)(2) groups, in accord with the tendency of simple arylboronic acids to form cyclic hydrogen-bonded dimers in the solid state. Five-fold interpenetrati...

From Head to Tail: Structure, Solvation, and Hydrogen Bonding of Carboxylate Surfactants at the OrganicWater Interface

Since ancient Babylonian times when soap-like materials were created for “washing the stones for servant girls”, carboxylate containing surfactants derived from the hydrolysis of fatty acids continue to be important today in industrial, commercial, and personal hygiene applications. In addition to being important in surfactant applications, carboxylate moieties are present in all amino acids, t...

Supramolecular PhanePhos-analogous ligands through hydrogen-bonding for asymmetric hydrogenation.

PhanePhos-analogous phosphorous ligands have been generated via self-assembly through hydrogen-bonding, and studied in rhodium-catalyzed asymmetric hydrogenation (up to 99% ee).

A supramolecular array of fullerenes by quadruple hydrogen bonding.

Supramolecular hydrogen-bonding assembly of silanediols with bifunctional heterocycles.

X-ray crystallography showcases the distinct self-association and hydrogen-bonding patterns of organic silanediols, R2Si(OH)2, with bifunctional heterocycles for supramolecular assembly. Diffusion-ordered spectroscopy (DOSY) studies identify the dominant hydrogen-bonding patterns and structures in solution, which correlate with solid-state patterns at high concentrations.