Synthesis and Chiroptical Properties of Alpha Chiral 2,5-Diaminoterephthalates

Baykal, Doruk
2,5-Diaminoterephthalates (DATs) are known to be intensely colored and fluorescent compounds that are quite open to functionalization. Even though their conjugated structure is significantly shorter/smaller than that of its popular counterparts such as fluoresceins and BODIPYs, they possess comparable optical properties. Most prominently, DATs have been used as organic linkers for metal organic framework (MOF) materials, and as fluorescent sensors. Despite the existence of chiral DAT derivatives, their chiroptical properties remain obscure. In this study, 6 novel chiral DAT derivatives were designed and synthesized. The designs were first evaluated in silico by DFT calculations. Their optical and chiroptical properties were explored using UV-Vis, fluorescence, and circular dichroism (CD) spectroscopies. In general, their optical properties showed dependence on the hydrogen bonding ability of the solvent, and hence showed promising properties as chiroptical sensors.


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Citation Formats
D. Baykal, “Synthesis and Chiroptical Properties of Alpha Chiral 2,5-Diaminoterephthalates,” M.S. - Master of Science, Middle East Technical University, 2022.