Chiang Mai Journal of Science

Photophysical Properties of Various Substituted Thiophene-based Heterocyclic Chalcone: Experimental and DFT Studies

Paper Type	Contributed Paper
Title	Photophysical Properties of Various Substituted Thiophene-based Heterocyclic Chalcone: Experimental and DFT Studies
Author	Nikorn Saengsuwan, Nutjarin Klinhom, Buchita Nakwanich, Suwannee Sriyab, Panida Prompinit, Songwut Suramitr, and Supa Hannongbua*
Email	fscisph@ku.ac.th
Abstract: A comprehensive study of the photophysical properties of three thiophene-based heterocyclic chalcones was investigated on the basis of joint optical spectroscopic technique and quantum chemical calculations. Three thiophene-based heterocyclic chalcone derivatives with 2,4,5-methoxy (2,4,5-OMe@Chal), 2,4,6-methoxy (2,4,6-OMe@Chal) and 3,4,5-methoxy (3,4,5- OMe@Chal) as terminal groups were focused. The thiophene-based heterocyclic chalcone, 2,4,5- OMe@Chal, 2,4,6-OMe@Chal and 3,4,5-OMe@Chal were synthesized, producing in 87%, 85% and 89% yields, respectively. The photophysical properties were performed by UV-Vis absorption and fluorescence spectroscopic technique. The obtained results indicated that the position of methoxy substituent groups brings to increasing in the fluorescence quantum yield (Фfluo). All the chalcone derivatives exhibit slightly low fluorescence quantum yields (Фfluo=0.0051-0.0518). In addition, Density Functional Theory (DFT) at PBE0/6-311G(d,p) level were successfully used to evaluate the molecular geometries, the characteristics of the excited singlet and triplet states. The calculated results were in well agreement with the experimental data, and indicated that the low fluorescence of 2,4,6-OMe@Chal and 3,4,5-OMe@Chal is derived from, not only intersystem crossing but also internal conversion due to the proximity effect. Among the three derivatives, it was found that 2,4,5-OMe@Chal shows higher fluorescence quantum yield than the others. This work deepens the understanding of thiophene-based heterocyclic chalcone derivatives and provides novel materials for improved fluorescence efficiencies.
Start & End Page	1176 - 1190
Received Date	2019-03-22
Revised Date
Accepted Date	2019-07-25
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Keyword	thiophene-based heterocyclic chalcone, photophysical properties, DFT calculations, fluorescence sensors
Volume	Vol.46 No.6 (November 2019)
DOI
Citation	Saengsuwan N., Klinhom N., Nakwanich B., Sriyab S., Prompinit P., Suramitr S., et al., Photophysical Properties of Various Substituted Thiophene-based Heterocyclic Chalcone: Experimental and DFT Studies, Chiang Mai J. Sci., 2019; 46(6): 1176-1190.
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