The Synthesis of Chiral Perylene and Naphthalene Diimides

ABSTRACT: In this thesis a new naphthalene monoimide, one chiral naphthalene diimide and two chiral perylene diimides have been successfully synthesized. The synthesized products were characterized through the data from NMR, IR, MS, UV-vis, DSC, TGA, elemental analysis, cyclic voltammetry, square-wave voltammetry and circular dichroism (CD). Naphthalene monoimide exhibits an intramolecular charge transfer complexation in its absorption spectrum in polar solvents. Excimer-like emissions were obtained in nonpolar, polar protic and aprotic solvents for naphthalene monoimide and diimide. The specific optical rotation values of unsymmetrical chiral naphthalene and perylene diimides were measured as -221.6, -24 and +200, respectively at 20 °C. All of the synthesized compounds showed high thermal and electrochemical stability. Chiral naphthalene diimide showed prominent negative Cotton effects centred at 362 and 382 nm in CH3CN. The results could lead to further development of sterically and stereochemically controlled conductive unsymmetrical diimides which could guide to design important optoelectronic devices. ……………………………………………………………………………………………………………………………………………………………………………………………………………………