A Way to Improve Luminescent Efficiency of Bis-Chalcone Derivatives
Chalcone related compounds have been reported as a poor luminescence molecule due to the quenching processes from the intramolecular torsional motions and cis-trans isomerization in the α,β-unsaturated ketone moiety. Despite this limitation, we found a way to improve the luminescent efficiency of ou...
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Wiley
2016-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2016/3608137 |
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| author | Meng Guan Tay Mee Hing Tiong Ying Ying Chia Suzie Hui Chin Kuan Zhi-Qiang Liu |
| author_facet | Meng Guan Tay Mee Hing Tiong Ying Ying Chia Suzie Hui Chin Kuan Zhi-Qiang Liu |
| author_sort | Meng Guan Tay |
| collection | DOAJ |
| description | Chalcone related compounds have been reported as a poor luminescence molecule due to the quenching processes from the intramolecular torsional motions and cis-trans isomerization in the α,β-unsaturated ketone moiety. Despite this limitation, we found a way to improve the luminescent efficiency of our bis-chalcone derivative. In this project, two series of bis-chalcone compounds have been synthesized through Claisen-Schmidt condensation by reacting terephthaldehyde or 2,5-dimethoxyterephthaldehyde with the respective R-acetophenone [where R = H (1a and 2a) and ortho-hydroxy (1b and 2b)] in 1 : 2 mole ratio. The presence of a methoxy (OMe) substituent on the central phenyl ring of bis-chalcone has weakened the C=C bond at the α,β-unsaturated ketone moiety of 2a and 2b. Interestingly, the OMe group has improved the emission efficiency of the bis-chalcone; that is, the quantum yield of 1a in DCM solution was not able to be determined due to poor luminescence, but the quantum yield of 2a in DCM solution was improved to 0.57. In addition, compound 2a also shows solvatochromism effect where the λmax emission shifted from 499 nm in nonpolar solvents (benzene) to 523 nm in polar solvents (acetonitrile). This work provides another way to improve the emission efficiency of chalcone related compounds apart from using the complexation method which has been reported before. |
| format | Article |
| id | doaj-art-d952fe5abf3e4c2387cccfd7eb246d50 |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2016-01-01 |
| publisher | Wiley |
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| series | Journal of Chemistry |
| spelling | doaj-art-d952fe5abf3e4c2387cccfd7eb246d502025-02-03T06:00:03ZengWileyJournal of Chemistry2090-90632090-90712016-01-01201610.1155/2016/36081373608137A Way to Improve Luminescent Efficiency of Bis-Chalcone DerivativesMeng Guan Tay0Mee Hing Tiong1Ying Ying Chia2Suzie Hui Chin Kuan3Zhi-Qiang Liu4Department of Chemistry, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, MalaysiaDepartment of Chemistry, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, MalaysiaDepartment of Chemistry, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, MalaysiaDepartment of Chemistry, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, MalaysiaState Key Laboratory of Crystal Materials, Shandong University, 27 Shanda South Road, Jinan 250100, ChinaChalcone related compounds have been reported as a poor luminescence molecule due to the quenching processes from the intramolecular torsional motions and cis-trans isomerization in the α,β-unsaturated ketone moiety. Despite this limitation, we found a way to improve the luminescent efficiency of our bis-chalcone derivative. In this project, two series of bis-chalcone compounds have been synthesized through Claisen-Schmidt condensation by reacting terephthaldehyde or 2,5-dimethoxyterephthaldehyde with the respective R-acetophenone [where R = H (1a and 2a) and ortho-hydroxy (1b and 2b)] in 1 : 2 mole ratio. The presence of a methoxy (OMe) substituent on the central phenyl ring of bis-chalcone has weakened the C=C bond at the α,β-unsaturated ketone moiety of 2a and 2b. Interestingly, the OMe group has improved the emission efficiency of the bis-chalcone; that is, the quantum yield of 1a in DCM solution was not able to be determined due to poor luminescence, but the quantum yield of 2a in DCM solution was improved to 0.57. In addition, compound 2a also shows solvatochromism effect where the λmax emission shifted from 499 nm in nonpolar solvents (benzene) to 523 nm in polar solvents (acetonitrile). This work provides another way to improve the emission efficiency of chalcone related compounds apart from using the complexation method which has been reported before.http://dx.doi.org/10.1155/2016/3608137 |
| spellingShingle | Meng Guan Tay Mee Hing Tiong Ying Ying Chia Suzie Hui Chin Kuan Zhi-Qiang Liu A Way to Improve Luminescent Efficiency of Bis-Chalcone Derivatives Journal of Chemistry |
| title | A Way to Improve Luminescent Efficiency of Bis-Chalcone Derivatives |
| title_full | A Way to Improve Luminescent Efficiency of Bis-Chalcone Derivatives |
| title_fullStr | A Way to Improve Luminescent Efficiency of Bis-Chalcone Derivatives |
| title_full_unstemmed | A Way to Improve Luminescent Efficiency of Bis-Chalcone Derivatives |
| title_short | A Way to Improve Luminescent Efficiency of Bis-Chalcone Derivatives |
| title_sort | way to improve luminescent efficiency of bis chalcone derivatives |
| url | http://dx.doi.org/10.1155/2016/3608137 |
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