title: Photoreactivity, Optical Behavior and DFT Studies of 2,5-Bis[4-choloro-acetyl(thiophen-2-ylmethylene)]cyclopentanone BCTCP in Different Solvents.
abstract: Diarylidenecyclopentanone compound namely, 2,5-bis[4-choloroacetyl-(thiophen-2-ylmethylene)]cyclopentanone (BCTCP) was firstly synthesized using the normal condition of Friedel-Crafts method by reacting 2,5-bis(thiophen-2-ylmethylene)cyclopentanone (BTCP) with chloroacetyl chloride in the presence of aluminum chloride anhydrous. The structure of this compound was confirmed by elemental and spectral analyses including FT-IR,1H-NMR,13C-NMR and mass spectrometry. The electronic absorption and emission properties of BCTCP were studied in different solvents. BCTCP displays a slight solvatochromic effect of the absorption and emission spectrum, indicating a small change in dipole moment of BCTCP upon excitation. BCTCP displayed photodecomposition in chlorinated solvents upon irradiating with 365 nm light. Ground and excited states electronic geometric optimizations were performed using density functional theory (DFT) and time-dependent density functional theory (TD-DFT), respectively. A DFT natural bond orbital (NBO) analysis complemented the intramolecular charge transfer (ICT). The simulated maximum absorption and emission wavelengths are in line the observed ones in trend, and were proportionally red-shifted with the increase of the solvent polarity. The stability, hardness and electrophilicity of BCTCP in different solvents were correlated with the polarity of the elected solvents.
authors.affiliation: Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah, 21589, Saudi Arabia.|Chemistry Department, Faculty of Science, Assiut University, Assiut, 71516, Egypt.
authors.forename: M A
authors.initials: MA
authors.lastname: Hussein
authors.affiliation: Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah, 21589, Saudi Arabia.|Chemistry Department, Faculty of Science, Khartoum University, P.O. Box 321, 11111, Khartoum, Sudan.
authors.forename: O I
authors.initials: OI
authors.lastname: Osman
authors.affiliation: Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah, 21589, Saudi Arabia.|Center of Excellence for Advanced Materials Research, King Abdulaziz University, P.O. Box 80203, Jeddah, 21589, Saudi Arabia.
authors.forename: A M
authors.initials: AM
authors.lastname: Asiri
authors.affiliation: Division of Bio-Resources Paper & Coating Technology, School of Industrial Technology, Universiti Sains Malaysia, Penang, Malaysia.
authors.forename: H D
authors.initials: HD
authors.lastname: Rozman
authors.affiliation: Chemistry Department, Faculty of Science, Tanta University, Tanta, 2173, Egypt. samyeldaly@yahoo.com.
authors.forename: S A
authors.initials: SA
authors.lastname: El-Daly
keywords: 2,5-bis[4-choloro-acetyl(thiophen-2-ylmethylene)]cyclopentanone; DFT calculations; Optical behavior; Photoreactivity