Photoreactivity, Optical Behavior and DFT Studies of 2,5-Bis[4-choloro-acetyl(thiophen-2-ylmethylene)]cyclopentanone BCTCP in Different Solvents

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 o...

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Bibliographic Details
Published in:Journal of fluorescence 2017-05, Vol.27 (3), p.1129-1140
Main Authors: Hussein, M. A., Osman, O. I., Asiri, A. M., Rozman, H. D., El-Daly, S. A.
Format: Article
Language:English
Subjects:
Absorption
Aluminum
Aluminum chloride
Analytical Chemistry
Biochemistry
Biological and Medical Physics
Biomedical and Life Sciences
Biomedicine
Biophysics
Biotechnology
Charge transfer
Chlorides
Decomposition reactions
Density functional theory
Dipole moments
Emission analysis
Mass spectrometry
NMR
Nuclear magnetic resonance
Original Article
Photodecomposition
Solvents
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Summary: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, 1 H–NMR, 13 C–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.
ISSN:1053-0509
1573-4994
DOI:10.1007/s10895-017-2048-8