title: Hexasubstituted Benzenes with Ultrastrong Dipole Moments.
abstract: 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.
authors.affiliation: Max-Planck-Institut für Polymerforschung, Ackermannweg 10, 55128, Mainz, Germany.
authors.forename: Jakob
authors.initials: J
authors.lastname: Wudarczyk
authors.affiliation: Department of Physics, University of Ioannina, 451 10, Ioannina, Greece.
authors.forename: George
authors.identifier: http://orcid.org/0000-0001-9257-5618
authors.initials: G
authors.lastname: Papamokos
authors.affiliation: Department of Physics, University of Ioannina, 451 10, Ioannina, Greece.
authors.forename: Vasilis
authors.initials: V
authors.lastname: Margaritis
authors.affiliation: Institute für Organische Chemie, Johannes-Gutenberg Universität Mainz, 55128, Mainz, Germany.
authors.forename: Dieter
authors.initials: D
authors.lastname: Schollmeyer
authors.affiliation: Max-Planck-Institut für Polymerforschung, Ackermannweg 10, 55128, Mainz, Germany.
authors.forename: Felix
authors.initials: F
authors.lastname: Hinkel
authors.affiliation: Max-Planck-Institut für Polymerforschung, Ackermannweg 10, 55128, Mainz, Germany.
authors.forename: Martin
authors.initials: M
authors.lastname: Baumgarten
authors.affiliation: Department of Physics, University of Ioannina, 451 10, Ioannina, Greece.
authors.forename: George
authors.initials: G
authors.lastname: Floudas
authors.affiliation: Max-Planck-Institut für Polymerforschung, Ackermannweg 10, 55128, Mainz, Germany. muellen@mpip-mainz.mpg.de.
authors.forename: Klaus
authors.initials: K
authors.lastname: Müllen
keywords: aromatic substitution; dielectric spectroscopy; dihydrobenzimidazoles; dipole moments; donor-acceptor systems