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

Humera Baig; Amber Iqbal; Alvina Rasool; Syed Zajif Hussain; Javed Iqbal; Meshari Alazmi; Nawaf Alshammari; Amira Alazmi; Amer AlGhadhban; Abdel Moneim E Sulieman; Kamaleldin B Said; Habib-Ur Rehman; Rahman Shah Zaib Saleem

doi:10.1021/acsomega.3c02813

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

ACS Omega. 2023 Jul 27;8(31):28499-28510. doi: 10.1021/acsomega.3c02813. eCollection 2023 Aug 8.

Affiliations

¹ Department of Chemistry and Chemical Engineering, Syed Babar Ali School of Science and Engineering, Lahore University of Management Sciences, Lahore 54792, Pakistan.
² Department of Chemistry, University of Agriculture, Faisalabad 38000, Pakistan.
³ College of Computer Science and Engineering, University of Ha'il, P.O. Box 2440, Ha'il 81481, Saudi Arabia.
⁴ College of Sciences, University of Ha'il, P.O. Box 2440, Ha'il 81481, Saudi Arabia.
⁵ Department of Science and Technology, University Colleges at Nairiyah, University of Hafr Al Batin, Nairiyah, 31981, Saudi Arabia.
⁶ College of Engineering, University of Ha'il, P.O. Box 2440, Ha'il 81481, Saudi Arabia.
⁷ Department of Pathology and Microbiology, College of Medicine, University of Ha'il, Ha'il, 55476, Saudi Arabia.

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 × 10⁴ 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.