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Abstract
The title chiral photochromic Schiff base compound, C21H19N3O, was synthesized from (R)-1-phenylethylamine and the salicylaldehyde of an azobenzene derivative. The molecule corresponds to the phenol–imine tautomer, the C=N and N—C bond distances being 1.279 (3) and 1.477 (3) Å, respectively. An intramolecular O—H⋯N hydrogen bond occurs. The diazenyl group adopts a trans form with an N=N distance of 1.243 (3) Å.
Highlights
The title chiral photochromic Schiff base compound, C21H19N3O, was synthesized from (R)-1-phenylethylamine and the salicylaldehyde of an azobenzene derivative
Comment In the recent years, we have developed organic-inorganic hybrid materials of photochromic compounds and chiral Schiff base metal complexes
We have developed chiral Schiff base liagnds to include chiral functions (Akitsu et al, 2004, 2006b; Miura et al, 2009)
Summary
The title chiral photochromic Schiff base compound, C21H19N3O, was synthesized from (R)-1-phenylethylamine and the salicylaldehyde of an azobenzene derivative. The molecule corresponds to the phenol–imine tautomer, the C N and N—C bond distances being 1.279 (3) and 1.477 (3) A , respectively. An intramolecular O—HÁ Á ÁN hydrogen bond occurs. The diazenyl group adopts a trans form with an N N distance of 1.243 (3) A. Related literature For applications of Schiff base–metal complexes and azobenzene, see: Akitsu & Einaga (2005a,b); Akitsu (2007); Akitsu & Itoh (2010). For Schiff base ligands, see: Akitsu et al (2004, 2006); Miura et al (2009); Hadjoudis & Mavridis (2004). For Schiff base compounds with an azobenzene group, see: Aslantaset al.
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