AbstractHexasubstituted benzenes have been synthesized with the highest known dipole moments, as determined by dielectric spectroscopy and DFT methods. Based on the preparation of 4,5‐diamino‐3,6‐dibromophthalonitrile, combined with a novel method to synthesize dihydrobenzimidazoles, these benzene derivatives have dipole moments in excess of 10 debye. Such dipole moments are desirable in ferroelectrics, nonlinear optics, and in organic photovoltaics. Structure determination was achieved through single‐crystal X‐ray crystallography, and the optical properties were determined by UV/Vis absorption and fluorescence spectroscopy.

AbstractWater was used as the solvent in the Petasis borono‐Mannich reaction. With the use of salicylaldehyde, secondary amines and boronic acids, several alkylaminophenols were obtained in considerably high yields in water. By using the same methodology, 2H‐chromenes were prepared with the use of vinyl boronic acids. The reaction mechanism was studied by DFT calculations, and the results obtained corroborate the solvent effect experimentally observed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)