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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
Full Text 
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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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Chiang Mai Journal of Science

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