THE ENANTIOSELECTIVE SYNTHESIS OF 2-INDOLYL-1-NITRO DERIVATIVES AND BODIPY DYES IN THE PRESENCE OF CHIRAL BIFUNCTIONAL SQUARAMIDE ORGANOCATALYSTS

Tez Türü: Doktora

Tezin Yürütüldüğü Kurum: Orta Doğu Teknik Üniversitesi, Fen Bilimleri Enstitüsü, Kimya, Türkiye

Tez Danışmanı: Cihangir Tanyeli

Tezin Onay Tarihi: 2022

Tezin Dili: İngilizce

Özet:

In our research group, chiral bifunctional squaramides with different basic units have been synthesized and evaluated in various asymmetric reactions. To test the catalytic activity of organocatalysts, Friedel-Crafts alkylation of indoles with nitroolefins was selected as a model reaction in the first part of the study. 19 different 2-indolyl-1- nitro derivatives were synthesized with up to >99% ee in the presence of sterically encumbered tert-butyl substituted squaramide/quinine. Besides, 2-adamantyl squaramide/quinine was evaluated in the addition of BODIPY core to isatin derivatives which will be the first example of this kind of enantioselective addition in literature. 6 novel chiral BODIPY dyes were synthesized with up to 60% ee, and their spectroscopic and chiroptical properties were investigated. In the final chapter, a point chiral at boron and carbon BODIPY was synthesized with a two-pot, onestep synthesis-an interrupted Knoevenagel condensation. ECD spectra of the dye showed a strong Cotton effect in the visible region. However, this dye showed weak fluorescence emission due to partly vibrational relaxations and bent-shaped molecular geometry.