Effect of Structural Variation on Spectral, NLO Properties, and Biological Activity of Pyrrole Hydrazones

[Image: see text] This paper describes spectral, non-linear optical (NLO), and biological activity variation of pyrrole hydrazones as a result of structural variation. In order to study structure–property variation, pyrrole hydrazones (3A, 3B, and 3C) were synthesized in both solid and solution phases. The grinding solvent-free method becomes rapid, easy, convenient, useful, sustainable, and eco-friendly green synthesis as compared to the classical solution phase reactions. The structure of pyrrole hydrazones has been elucidated by microanalysis and quantum chemical calculations. The intense emission at λ(em) 521 nm (3A and 3B) and 617 nm (3C) in the visible (green and orange) region with Stokes shifts at 195, 160, and 282 nm reveals that the studied compounds work as good photoluminescent materials. All compounds show strong n−π* and charge transfer (π–π*) transitions in the UV–vis region with high extinction coefficients. In the studied systems (3A, 3B, and 3C), the orbital overlap between σ(NH–O) → σ*(NH–O) is found due to intra-molecular charge transfer. The first hyperpolarizabilities were found to be 48.83 × 10(–30) esu for 3B and 63.89 × 10(–30) esu for 3C, showing variation with structure. Their high values indicate more suitability for NLO application. Incorporation and/or change in position of electron-withdrawing groups increase the β(0) values of 3B and 3C compared to 3A. The β value also increases monotonically as the polarity of the solvents increases. The red shift in N–H and C=O stretching Fourier-transform infrared bonds is due to the formation of dimers. The synthesized 3A, 3B, and 3C show good antimicrobial activity and are predicted to be potential antibacterial and antifungal drugs. The 3B has more molar refractivity (122.16 esu) than 3A and 3C and correlates well with the calculated binding affinity and experimental antimicrobial data.