Abstract
The title compound, (systematic name: N,N'-dibenzyl-3,3'-dimeth-oxy-1,1'-biphenyl-4,4'-di-amine), C28H28N2O2, was synthesized by the reduction of a Schiff base prepared via a condensation reaction between o-dianisidine and benzaldehyde under acidic conditions. The mol-ecule lies on a crystallographic inversion centre so that the asymmetric unit contains one half-mol-ecule. The biphenyl moiety compound is essentially planar. Two intra-molecular N-H⋯O hydrogen bonds occur. The dihedral angle between the terminal phenyl and phenyl-ene rings of a benzidine unit is 48.68 (6)°. The methyl-ene C atom of the benzyl group is disordered over two sets of sites, with occupancy ratio 0.779 (18):0.221 (18). In the crystal, mol-ecules are connected by hydrogen bonding between o-dianisidine O atoms and H atoms of the terminal benzyl groups, forming a one-dimensional ladder-like structure. In the data from DFT calculations, the central biphenyl showed a twisted conformation.
Highlights
The title compound, C28H28N2O2, was synthesized by the reduction of a Schiff base prepared via a condensation reaction between o-dianisidine and benzaldehyde under acidic conditions
The methylene C atom of the benzyl group is disordered over two sets of sites, with occupancy ratio 0.779 (18):0.221 (18)
Molecules are connected by hydrogen bonding between o-dianisidine O atoms and H atoms of the terminal benzyl groups, forming a one-dimensional ladder-like structure
Summary
Benzidine derivatives have received increasing attention in recent years beacuse of their applications in a wide variety of domains, for instance as building blocks in the construction of functionalized organic/organometallic materials and as sensor materials (Hmadeh et al, 2008; Satapathi, 2015; Nagaraja et al, 2017). Benzidine derivatives are relevant examples of simple redox systems, which could find applications as OLEDs (Zhang et al, 2004) or electroactive organic polymeric compounds (D’Eramo et al, 1994). We have reported copper(I) coordination polymers based on pyromellitic diimide derivatives, and shown that photoluminescence emission peaks are shifted depending on the solvent (Kang et al, 2015). In an extension of previous research, we have synthesized a benzidine derivative as a diamine intermediate, in which a benzidine moiety was used instead of a pyromellitic diimide spacer unit, and report its crystal structure here.
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