Supramolecular assembly and spectroscopic characterization of indolenine–barbituric acid zwitterions
A series of indolenine and barbituric acid zwitterion scaffolds were synthesized with a maximum yield of 98% via the formation of C–C single bond. The structures were unambiguously elucidated by various spectroscopic techniques such as 1H, 13C NMR (1D, 2D), FT-IR and high-resolution mass spectromet...
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Royal Society of Chemistry
2021
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| Online Access: | http://eprints.sunway.edu.my/1566/ http://eprints.sunway.edu.my/1566/1/Tiekink%20acc_new%20j%20chem%202021%2045%201221.pdf |
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| author | Ramle, Abdul Qaiyum Tiekink, Edward R. T. * Fei, Chee Chin Julkapli, Nurhidayatullaili Muhd Basirun, Wan Jefrey |
| author_facet | Ramle, Abdul Qaiyum Tiekink, Edward R. T. * Fei, Chee Chin Julkapli, Nurhidayatullaili Muhd Basirun, Wan Jefrey |
| author_sort | Ramle, Abdul Qaiyum |
| building | SU Institutional Repository |
| collection | Online Access |
| description | A series of indolenine and barbituric acid zwitterion scaffolds were synthesized with a maximum yield of 98% via the formation of C–C single bond. The structures were
unambiguously elucidated by various spectroscopic techniques such as 1H, 13C NMR (1D, 2D), FT-IR and high-resolution mass spectrometry (HRMS). Single crystal X-ray
crystallography analysis on 22, as the 22.DMF 1:1 solvate, confirms the presence of wellseparated iminium and enolate centres, and also confirms that the BA ring is highly twisted with respect to the indolenine ring due to steric hindrance. The presence of N–H∙∙∙O and N–H∙∙∙O- groups favour a 1D-supramolecular assembly in the solid-state. The orange or yellow solutions of the zwitterion exhibit an intense molar absorption coefficient, ε ranging between
0.21 × 104 and 2.93 × 104 M-1 cm-1 in the UV-vis region. Furthermore, the Intramolecular Charge Transfer (ICT) peak of zwitterion displays a hypsochromic shift in absorption
behavior when the polarity of the solvent increases. Moreover, treatment of small amount of trifluoroacetic acid (TFA) to the DMF solution of 19 resulted in the protonation of an enolate of BA ring. This fundamental work provides valuable structural design and information for
the construction of supramolecular chemistry and synthetic dyes based on indolenine substituted BA derivatives. |
| first_indexed | 2025-11-14T21:17:47Z |
| format | Article |
| id | sunway-1566 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:17:47Z |
| publishDate | 2021 |
| publisher | Royal Society of Chemistry |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | sunway-15662021-01-27T06:35:10Z http://eprints.sunway.edu.my/1566/ Supramolecular assembly and spectroscopic characterization of indolenine–barbituric acid zwitterions Ramle, Abdul Qaiyum Tiekink, Edward R. T. * Fei, Chee Chin Julkapli, Nurhidayatullaili Muhd Basirun, Wan Jefrey QD Chemistry A series of indolenine and barbituric acid zwitterion scaffolds were synthesized with a maximum yield of 98% via the formation of C–C single bond. The structures were unambiguously elucidated by various spectroscopic techniques such as 1H, 13C NMR (1D, 2D), FT-IR and high-resolution mass spectrometry (HRMS). Single crystal X-ray crystallography analysis on 22, as the 22.DMF 1:1 solvate, confirms the presence of wellseparated iminium and enolate centres, and also confirms that the BA ring is highly twisted with respect to the indolenine ring due to steric hindrance. The presence of N–H∙∙∙O and N–H∙∙∙O- groups favour a 1D-supramolecular assembly in the solid-state. The orange or yellow solutions of the zwitterion exhibit an intense molar absorption coefficient, ε ranging between 0.21 × 104 and 2.93 × 104 M-1 cm-1 in the UV-vis region. Furthermore, the Intramolecular Charge Transfer (ICT) peak of zwitterion displays a hypsochromic shift in absorption behavior when the polarity of the solvent increases. Moreover, treatment of small amount of trifluoroacetic acid (TFA) to the DMF solution of 19 resulted in the protonation of an enolate of BA ring. This fundamental work provides valuable structural design and information for the construction of supramolecular chemistry and synthetic dyes based on indolenine substituted BA derivatives. Royal Society of Chemistry 2021 Article PeerReviewed text en cc_by_nc_4 http://eprints.sunway.edu.my/1566/1/Tiekink%20acc_new%20j%20chem%202021%2045%201221.pdf Ramle, Abdul Qaiyum and Tiekink, Edward R. T. * and Fei, Chee Chin and Julkapli, Nurhidayatullaili Muhd and Basirun, Wan Jefrey (2021) Supramolecular assembly and spectroscopic characterization of indolenine–barbituric acid zwitterions. New Journal of Chemistry, 45 (3). pp. 1221-1230. ISSN 1144-0546 (Submitted) http://doi.org/10.1039/D0NJ04357E doi:10.1039/D0NJ04357E |
| spellingShingle | QD Chemistry Ramle, Abdul Qaiyum Tiekink, Edward R. T. * Fei, Chee Chin Julkapli, Nurhidayatullaili Muhd Basirun, Wan Jefrey Supramolecular assembly and spectroscopic characterization of indolenine–barbituric acid zwitterions |
| title | Supramolecular assembly and spectroscopic characterization of indolenine–barbituric acid zwitterions |
| title_full | Supramolecular assembly and spectroscopic characterization of indolenine–barbituric acid zwitterions |
| title_fullStr | Supramolecular assembly and spectroscopic characterization of indolenine–barbituric acid zwitterions |
| title_full_unstemmed | Supramolecular assembly and spectroscopic characterization of indolenine–barbituric acid zwitterions |
| title_short | Supramolecular assembly and spectroscopic characterization of indolenine–barbituric acid zwitterions |
| title_sort | supramolecular assembly and spectroscopic characterization of indolenine–barbituric acid zwitterions |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/1566/ http://eprints.sunway.edu.my/1566/ http://eprints.sunway.edu.my/1566/ http://eprints.sunway.edu.my/1566/1/Tiekink%20acc_new%20j%20chem%202021%2045%201221.pdf |