STUDIES ON CHIROPTICAL PROPERTIES OF 2-CARBOXY-5,6-BENZOCOUMARIN: EFFECT OF SIDE CHAIN

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2022-10-21

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Öztürk, Perihan

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The synthesis and examination of chiroptical materials are essential for their considerable potential in diverse applications. With that, induced chirality is a particular condition for the design of chiroptical compounds where the chiral information of a chiral compound is transferred to a UV-Vis reporter. This approach allows the utilization of numerous chiral compounds for chiroptical studies. Accordingly, in this study, the use of 2-carboxy-5,6-benzocoumarin (3-oxo-3H- benzo[f]chromene-2-carboxylic acid) in chiroptical studies was investigated. Novel chiroptical compounds comprising 2-carboxy-5,6-benzocoumarin as a reporter, alanine, phenylalanine, trans-cyclohexanediamine and tartaric acid as chiral units have been synthesized and fully characterized. The spectroscopic analyses of these compounds showed that the compounds could not be distinguished due to the identical chromophore units in the structures. Consequently, the chiroptical compounds were examined through CD spectroscopy. All synthesized chiroptical materials provided chiroptical signals proving that 2- carboxy-5,6-benzocoumarin is a suitable UV-Vis reporter for chiroptical studies. The effect of altering the ethylene glycol side chain on CD spectra was examined in selected solvent environments and the presence of alkali metals. The CD regions that were affected could be determined. This study showed that chiroptical signals generated by benzocoumarin units depend not only on the chiral units attached but also on achiral side-chain conformations. Besides, increasing the stereogenic centers in the structure was observed to enhance the chiroptical signal drastically. With this study, it was shown that tartaric acid benzocoumarin conjugates could be used in chirality sensing studies.

Subject Keywords

induced chirality, chiroptical sensing, benzocoumarin, CD spectroscopy

URI

https://hdl.handle.net/11511/99787

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Graduate School of Natural and Applied Sciences, Thesis

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Citation Formats

P. Öztürk, “STUDIES ON CHIROPTICAL PROPERTIES OF 2-CARBOXY-5,6-BENZOCOUMARIN: EFFECT OF SIDE CHAIN,” Ph.D. - Doctoral Program, Middle East Technical University, 2022.