Organic Multifunctional Materials: Second Harmonic, Ferroelectric, and Dielectric Properties in N-Benzylideneaniline Analogues

Abstract

The search for multifunctional organic compounds that display technologically important properties has been pursued in recent years. Here we report the synthesis and structure of a series of single-component N-benzylideneaniline analogues 4-(4-(4-nitrobenzylideneamino)­benzyl)­oxazolidin-2-one (NBOA), 4-(4-(4-chlorobenzylideneamino)­benzyl)­oxa-zolidin-2-one (CBOA), and 4-(4-(4-hydroxybenzy-lideneamino)­benzyl)­oxazolidin-2-one (HBOA). The dynamic disorder observed in the structure of NBOA is investigated using variable temperature single crystal X-ray diffraction. All three compounds display second harmonic generation, well-defined PE loops with hysteresis at room temperature typical of ferroelectric materials, and significant dielectric behavior with tolerance toward high electric fields.

(E)-N,N-Diethyl-4-{[(4-methoxyphenyl)imino]methyl}aniline: crystal structure, Hirshfeld surface analysis and energy framework

“…A full search of the CSD for p-substituted benzylideneanilines gave 229 hits for entries that fitted the following criteria: three-dimensional coordinates available, R � 0.075, no disorder, no errors, no polymers, no ions, organics only and only single crystal analyses. An analysis using Mercury (Macrae et al, 2020) of the dihedral angle A/B indicated that it can vary from 0.9 � for (E)-4-{4-[(4-chlorobenzylidene)amino]-benzyl}oxazolidin-2-one (FORYIX; Kumari et al, 2019)…”

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Multifunctional Oxazolone Derivative as an Optical Amplifier, Generator, and Modulator

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