Synthesis and Photophysical, Electrochemical, and DFT Studies of Piperidyl and Pyrrolidinyl Chalcones

Abstract

Small organic molecules with interesting optical and electrochemical properties find applications as organic luminescent materials. In this work, we report the synthesis of novel chalcones with D−A−D and D−A−D−A architecture, followed by their optical, electrochemical, and computational studies. The absorption band of these compounds occurs at 360−480 nm with emission maxima appearing around 513−552 nm. The large Stokes shifts (Δλ) for all compounds (90−132 nm) suggest intramolecular charge transfer (ICT) in the excited states. The molar absorptivity and fluorescence quantum yields were found to be in the range of 1.7−4.26 × 10 4 M −1 cm −1 and 0.29−0.39, respectively. The electrochemical parameters were determined by using cyclic voltammetry (CV). Density functional theory (DFT) calculations of all compounds were made by using B3LYP/G (d,p) functionals in chloroform and were found to have a good correlation with experimental results. Preliminary studies of absorption, photoluminescence, CV, and their theoretical correlation suggest that these compounds may be optimized for their applications in optoelectronics, sensing, and bioimaging.

Electrochemical and Theoretical Modelled Reduction of β‐Diketone Inspired Chalcones

“…[29,30] The electrochemical properties of various chalcones have been demonstrated using a three-electrode cell system in the presence of anhydrous acetonitrile and tetrabutylammonium hexafluorophosphate electrolyte. [31][32][33] In addition, Slobodinyuk et al reported the electrochemical oxidation of series of asymmetric chalcones. [34] Kagatikar and co-workers assessed pyrene-based chalcones as functional materials applicable in organic electronics.…”

“…Some reported metal complexes of chalcones also exhibit antihyperglycemic and antimicrobial activities [29,30] . The electrochemical properties of various chalcones have been demonstrated using a three‐electrode cell system in the presence of anhydrous acetonitrile and tetrabutylammonium hexafluorophosphate electrolyte [31–33] . In addition, Slobodinyuk et al reported the electrochemical oxidation of series of asymmetric chalcones [34] .…”