Effect of tetraethylene glycol side chain conformation on chiroptical properties of chirality-induced benzocoumarin

Date

2022-10-01

Author

Öztürk, Perihan
Akdağ, Akın

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Coumarins are multifaceted molecules with compelling fluorescence features. Along with biocompatible properties, they have recently been used in chiroptical studies. The chirality induction to benzo[f]coumarin moiety at the third position was investigated in this study. The chromophore derivatized with homochiral alanine and phenylalanine resulted in identical spectroscopic properties. When the chiroptical properties are concerned, the distinct CD spectra of both structures are also changed significantly by altering the organic solvent. Inter- and intra-molecular hydrogen bonding affects the CD spectra along with the chiroptical signal. The phenylalanine-benzo[f]coumarin structures were modified with TEG units to increase water solubility and enhance ordered aggregations. The chiroptical properties of the compounds were analyzed in organic solvents with spectroscopic techniques. It was found that coumarin is not only sensitive to the chiral unit attached but also that any conformational change on the side chain affects the chiroptical signal. Time-dependent DFT calculations in the gas phase supported these results.

Subject Keywords

aggregation, chirality, chiroptical, circular dichroism, conformation, COUMARIN DERIVATIVES, CIRCULAR-DICHROISM, RATIONAL DESIGN, AMINO-ACIDS, FLUORESCENCE, PROBES

URI

https://hdl.handle.net/11511/99946

Journal

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY

DOI

https://doi.org/10.1002/poc.4453

Collections

Department of Chemistry, Article

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Citation Formats

P. Öztürk and A. Akdağ, “Effect of tetraethylene glycol side chain conformation on chiroptical properties of chirality-induced benzocoumarin,” JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, pp. 0–0, 2022, Accessed: 00, 2022. [Online]. Available: https://hdl.handle.net/11511/99946.