SYNTHESIS OF NOVEL CARBAZOLE DERIVATIVES BY DIELS-ALDER REACTION OF INDOLE-BASED DIENES WITH VARIOUS DIENOPHILES

Date

2023-9-11

Author

BATUR, DİLAN

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Diels-Alder reaction is a powerful tool in organic synthesis to produce complicated molecular structures. This thesis aims to synthesize functionalized carbazole derivatives using the Diels-Alder reaction of indole-based dienes with various dienophiles. The chemistry of carbazoles has generated interest in medicinal chemistry and natural product synthesis in the labs due to its diverse biological activity. Furthermore, carbazoles are used in optoelectronic devices due to the wide band gap and charge transport properties. Four dienes having 5-bromo, 7-bromo, N-H, and N-Me indole units were synthesized and reacted with N-methyl-, N-phenyl- and N-benzylmaleimides by the Diels-Alder reaction. In order to obtain the carbazole derivatives in high yields, Diels-Alder reaction conditions were optimized first. Optimization studies started with different catalysts and continued with different solvents, temperatures, and catalyst loads to achieve the highest yield of the desired carbazole cycloadducts. All the optimization studies were done using N-methylindole substituted diene and N-methylmaleimide dienophile. Synthesized carbazole derivatives were characterized by spectroscopic techniques like NMR, IR, and mass spectrometry. Besides, the synthesis of novel carbazole derivatives, photophysical properties were also investigated to determine their potential use in optoelectronic devices such as OLED and solar cell applications.

Subject Keywords

Carbazoles, Indole-substituted dienes, Diels-Alder reaction

URI

https://hdl.handle.net/11511/105508

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Graduate School of Natural and Applied Sciences, Thesis