Synthesis and Characterization of a New Perylene Anhydride Derivative Functionalized at the Bay Region

Perylene chromophore has an outstanding aromatic conjugation. The functionalization at the bay and imide positions brings great advantages. Specifically, functionalization at the bay region via long alkyl chain improves the solubility as well as the optical and electrochemical properties. In this thesis study, we have synthesized a new bay-substituted perylene dianhydride, (1,7-di(2-decyl-1-tetradecanoyl)-perylene-3,4,9,10-tetracarboxylic dianhydride; decanol-PDA) in two steps. In the first step, the bay positions (1, 7-positions) of perylene dianhydride (PDA) were brominated (Br-PDA). In the second step, the targeted bay substituted perylene dianhydride (decanol-PDA) was synthesized through bay substitution of perylene core with 2-decyl-1-tetradecanol. The product was purified and characterized by using FTIR spectroscopy, UV-vis spectroscopy and emission spectroscopy. Expectively, the synthesized product showed enhanced solubility comparing perylene anhydride. The UV-vis absorption spectra of the two synthesized perylene derivatives in nonpolar solvents showed three characteristic absorption bands, that are belonging to π–π* electronic transitions of perylene chromophore. While, the UV-vis absorption spectra in dipolar aprotic solvents showed additional absorption bands at higher wavelength. The emission spectra of the synthesized compounds showed excimer-like emission spectra in nonpolar and dipolar aprotic solvent. Keywords: Perylene dianhydride, bay-substitution, optical and photophysical properties.