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, DOI https://doi.org/10.1039/d0nj04357e.
Full text not available from this repository.Abstract
A series of indolenine and barbituric acid zwitterion scaffolds were synthesized with a maximum yield of 98% via the formation of C-C single bonds. The structures were unambiguously elucidated by various spectroscopic techniques such as H-1, C-13 NMR (1D and 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 well-separated 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-HMIDLINE HORIZONTAL ELLIPSISO- and N-HMIDLINE HORIZONTAL ELLIPSISO- groups favours 1D-supramolecular assembly in the solid-state. The orange or yellow solutions of the zwitterion exhibit an intense molar absorption coefficient, epsilon, ranging between 0.21 x 10(4) and 2.93 x 10(4) M-1 cm(-1) in the UV-vis region. Furthermore, the Intramolecular Charge Transfer (ICT) peak of the zwitterion displays a hypsochromic shift in the absorption behavior when the polarity of the solvent increases. Moreover, treatment with a small amount of trifluoroacetic acid (TFA) with the DMF solution of 19 resulted in the protonation of the enolate of the 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.
| Item Type: | Article |
|---|---|
| Funders: | Universiti Malaya (IIRG010B-2019), Universiti Malaya (ST011-2019), Universiti Malaya (STR-RCTR-RCCM-001-2019), Sunway University Sdn (STR-RCTR-RCCM-001-2019) |
| Uncontrolled Keywords: | Supramolecular assembly; Spectroscopic characterization; Indolenine-barbituric acid zwitterions |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Department of Chemistry Deputy Vice Chancellor (Research & Innovation) Office > Nanotechnology & Catalysis Research Centre |
| Depositing User: | Ms Zaharah Ramly |
| Date Deposited: | 25 Jul 2022 03:16 |
| Last Modified: | 25 Jul 2022 03:16 |
| URI: | http://eprints.um.edu.my/id/eprint/28100 |
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