Synthesis, structural, vibrational spectral, nonlinear optical, electron transfer studies of N-(5-chloro-2-hydroxyphenyl)-(3-bromo-6-oxocyclohexa-2,4-dienylidene)methylamine

• The first-order hyperpolarizability is nearly eight times that of urea.
• The studied molecule presents the molecular battery characteristics.
• The studied molecule is an excellent semiconductor device with gap 3.059 eV.

In recent years, the imine-bridged organics has been one of the hot spots in the field of photo-responsive materials. Herein, N-(5-chloro-2-hydroxyphenyl)-(3-bromo-6-oxocyclohexa-2,4-dienylidene)-methylamine (CHPBOCDMA) was synthesized and characterized by a combined experimental and theoretical method. CHPBOCDMA adopts trans configuration about the central methylamine bond. The vibrational spectral bands were assigned to the molecular structure in details. The vibrational spectrum has been recorded and analyzed. Theoretic calculations provide the parameters of thermodynamics, NLO, atomic charges, frontier molecular orbitals and natural bond orbitals. The mean linear polarizability and first-order hyperpolarizability calculated at B3LYP/6-311+G(d,p) level are of 36.4292 Å3 and 45.0911 × 10−31 cm5/esu, respectively. CHPBOCDMA is a molecular semiconductor by seven directional batteries connected in a parallel–series mode, which can transport electrons in a long range. The HOMO and LUMO orbitals with the energy gap of 3.059 eV are responsible for the optical and electron-transfer properties of the studied compound. The photoresponse-related results indicate the compound will be an excellent organic candidate of photon-responsive materials.

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