Synthesis and characterization of fluorenone derivatives with electrical properties explored using density functional theory (DFT)

Muhammad Umar Farooq; Malaika Muneer; Ali Shahid; Muhammad Abdul Rehman; Khalil Ullah; Ghulam Murtaza; Rashid Iqbal; Javed Iqbal; Mehdi Rahimi

doi:10.1038/s41598-024-80477-0

Synthesis and characterization of fluorenone derivatives with electrical properties explored using density functional theory (DFT)

Sci Rep. 2024 Nov 22;14(1):29015. doi: 10.1038/s41598-024-80477-0.

Authors

Muhammad Umar Farooq¹, Malaika Muneer², Ali Shahid³, Muhammad Abdul Rehman³, Khalil Ullah⁴, Ghulam Murtaza^{5

6}, Rashid Iqbal^{7

8}, Javed Iqbal⁹, Mehdi Rahimi¹⁰

Affiliations

¹ Physical Chemistry of Metallurgical and Energy Engineering Department, Kunming University of Science and Technology, Kunming, 650500, People's Republic of China.
² Institute of Chemistry, Khwaja Fareed University of Engineering and Information Technology, Rahim Yar Khan, 64200, Pakistan.
³ Department of Materials Science and Engineering, Kunming University of Science and Technology, Kunming, 650500, People's Republic of China.
⁴ Faculty of Information Engineering and Automation, Kunming University of Science and Technology, Kunming, People's Republic of China.
⁵ School of Agriculture, Yunnan University, Kunming, 650504, Yunnan, People's Republic of China. murtazabotanist@gmail.com.
⁶ School of Ecology and Environmental Sciences, Biocontrol Engineering Research Center of Crop Diseases and Pests, Yunnan University, Kunming, 650500, Yunnan, People's Republic of China. murtazabotanist@gmail.com.
⁷ Department of Agronomy, Faculty of Agriculture and Environment, The Islamia University of Bahawalpur, Bahawalpur, 63100, Pakistan. rashid.iqbal@iub.edu.pk.
⁸ Department of Life Sciences, Western Caspian University, Baku, Azerbaijan. rashid.iqbal@iub.edu.pk.
⁹ Department of Botany, Bacha Khan University, Khyber Pakhtunkhwa, 24420, Charsadda, Pakistan.
¹⁰ Department of Biotechnology, Institute of Science and High Technology and Environmental Sciences, Graduate University of Advanced Technology, Kerman, Iran. mehdi83ra@yahoo.com.

Abstract

This study provides thorough computational and experimental assessments of four types of novel synthesized thiosemicarbazones. The compounds were effectively synthesized using a condensation reaction between thiosemicarbazide and fluorenone, producing a remarkable range of 70-88%. Additional chemical structures were examined utilizing spectroscopic methods, including Fourier-transform infrared spectroscopy (FTIR), NMR spectroscopy, and ultraviolet-visible spectroscopy. The computational analyses utilized DFT using the M06/6-311G (d, p) technique. The electrical characteristics, including the stability of orbitals via energy exchange between a donor and acceptor, can be evaluated by natural bond orbital (NBO) analysis. The nonlinear optical (NLO) properties were analyzed to detect any prohibited energy gaps. FTIR and UV-visible data were computed using the identical M06/6-311G (d, p) level of theory. The NBO test has confirmed the occurrence of charge separation due to the efficient transfer of electrons from the donor to the acceptor unit over the π bridge. The molecular chemical softness and hardness are dependable indications of a molecule's chemical stability. A significant magnitude of the absolute value of polarizability and hyper-polarizability indicates considerable dispersion of electric charge. The outcomes derived from Density Functional Theory (DFT) generally align well with experimental findings.

Keywords: Chemical stability; Chemical structures; DFT; Fluorenone; Thiosemicarbazide.