SYNTHESIS OF SOME CARBAZOLE-DERIVED MOLECULES AND INVESTIGATION OF THEIR ELECTROCHEMICAL AND PHOTOPHYSICAL PROPERTIES


Görgün K., Derince B., Hür E.

International Conference on Basic Sciences and Technology (ICBAST), Antalya, Turkey, 16 - 19 November 2023, pp.9, (Summary Text)

  • Publication Type: Conference Paper / Summary Text
  • City: Antalya
  • Country: Turkey
  • Page Numbers: pp.9
  • Eskisehir Osmangazi University Affiliated: Yes

Abstract

Carbazole is an aromatic compound due to its conjugated double bond system. Aromatic stability is achieved through the delocalization of π-electrons across the two benzene rings and the nitrogen atom. It is noteworthy that electron-withdrawing groups such as -F, -CN, -CF3 are commonly used to adjust the electronic properties of carbazole derivatives. The fluorine atom, possessing high electronegativity and a small atomic radius, has the capacity to modulate molecular energy levels and enhance electron mobility when attached as a substituent to the molecule. Structures containing C-F bonds are extensively employed in biomedical active systems and electronic material design (such as OLEDs, DSSCs). Organic compounds containing fluorine atoms gain high stability against oxidation due to their lower HOMO/LUMO energy levels. Additionally, these compounds exhibit increased reduction potentials, facilitating the electrochemical decomposition of fluorine compounds. In this study, two carbazole-based compounds 3,6-bis(4-(trifluoromethyl)phenyl)-9-octyl-9Hcarbazole (IVa) and 3,6-bis(3,4,5-trifluorophenyl)-9-octyl-9H-carbazole (IVb) was synthesized via the Suzuki-Miyaura cross-coupling reaction (Scheme 1). The photophysical and thermal properties of this compound were determined by UV-Vis, thermogravimetric analysis (TGA) and differential thermal analysis (DTA). The oxidation potentials of the molecules were determined on the gold electrode surface in dichloromethane solution containing tetrabutylammonium hexafluorophosphate using the cyclic voltammetry method. The HOMO and band gap (Eg,opt) energies were calculated from oxidation potential and absorption bands. Similarities in the electronic structures of compounds with similar structures containing CF3 and F were identified using the obtained data.