Hexasubstituted Benzenes with Ultrastrong Dipole Moments. Issue 9 (2nd February 2016)

• Record Type: Journal Article
• Authors: Wudarczyk, Jakob; Papamokos, George; Margaritis, Vasilis; Schollmeyer, Dieter; Hinkel, Felix; Baumgarten, Martin; Floudas, George; Müllen, Klaus
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 9(2016)
• Page Start: 3220
• Page End: 3223
• Publication Date: 2016-02-02
• Subjects: aromatic substitution -- dielectric spectroscopy -- dihydrobenzimidazoles -- dipole moments -- donor–acceptor systems; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201508249
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : Just a moment : Molecules with high dipole moments are desirable materials for organic electronic applications such as nonlinear optics and ferroelectrics. Hexasubstitution of benzene and a novel method to synthesize dihydrobenzimidazoles has allowed charge‐free compounds to be generated with dipole moments above 10 debye.