Nonlinear optical properties of pyrene-based chalcone: (E)-1-(4′-bromo-[1,1′-biphenyl]-4-yl)-3-(pyren-1-yl)prop-2-en-1-one, a structure-activity study

Abstract

The presence of C-H…O and π … π stacking, which form a head to tail and face to face arrangement chain along the b-axis, was shown by single crystal analysis. The small dihedral angle between the pyrene and bromo-biphenyl rings increases the overall molecule's conjugation, and the low dihedral angles between the enone group (acceptor) and both pyrene and bromo-biphenyl moieties (donors) show the molecule's high ICT characteristic. Theoretical studies were conducted utilising density functional theory (DFT) at the B3LYP,6-311++G (d,p) basis set. ICT transfer from pyrene and bromo biphenyl moieties to carboxyl group was observed using HOMO-LUMO diagrams and Hirshfeld surfaces analysis, generating a D-π-A-π-D type push-pull system. Z-scan open and closed aperture plots were used to obtain nonlinear optical characteristics of BBPP. The self-defocusing reaction is visible in the Z-scan results, which indicate a negative nonlinear refractive index. The optical limiting behavior of the crystal is also promising. The titled crystal is a promising material for NLO devices based on the NLO characteristics of BBPP.