Occasionally, someone comments about an old post here, asking a question. Such was the case here, when a question about the dipole moment of cyclopropenylidene arose. It turned out to be 3.5D, but this question sparked a thought about the related molecule below.
Published in Angewandte Chemie International Edition
Authors Jakob Wudarczyk, George Papamokos, Vasilis Margaritis, Dieter Schollmeyer, Felix Hinkel, Martin Baumgarten, George Floudas, Klaus Müllen
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.