6533b850fe1ef96bd12a85e9

RESEARCH PRODUCT

Hexasubstituted Benzenes with Ultrastrong Dipole Moments

Martin BaumgartenDieter SchollmeyerVasilis MargaritisGeorge FloudasFelix HinkelJakob WudarczykGeorge PapamokosKlaus Müllen

subject

Organic solar cellChemistryNonlinear optics02 engineering and technologyGeneral ChemistryElectrophilic aromatic substitution010402 general chemistry021001 nanoscience & nanotechnology01 natural sciencesCatalysisFluorescence spectroscopy0104 chemical sciencesDielectric spectroscopyDipoleNuclear magnetic resonanceBenzene derivativesPhysical chemistry0210 nano-technologyAbsorption (electromagnetic radiation)

description

Hexasubstituted 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.

https://doi.org/10.1002/anie.201508249