Bulletin of the Chemical Society of Ethiopia

Log in or Register to get access to full text downloads.

Remember me or Register

A rational synthesis of a novel imidazo[4,5-f][1,10]phenanthroline templated Schiff base: Characterization, photoluminescence and DFT/TD-DFT study

S. Karslıoğlu, S. Demir, H. Yılmaz, S. Gördük


A new imidazo[4,5-f][1,10]phenanthroline (imp) derivative imidazo-N5,N6-bis((4-(1H-imidazo[4,5-f][1,10]phenanthroline-2-yl)phenyl)methylene)-1,10-phenanthroline-5,6-diamine (impap) was synthesized in five steps starting from bare phenanthroline (phen) precursors. The novel compound was fully characterized by 1H-NMR, IR, elemental analysis and electrospray ionization mass spectroscopy (ESI-MS) techniques. Solid state emission spectrum of impap showed two distinct strong emission maxima with large Stokes shifts. The ground state gas phase geometry of impap was predicted by DFT calculations. Excited state properties of the molecule were examined through TD-DFT calculations conducted at the optimized geometry. Responsible transitions for the strong fluorescence of impap were assigned to single component charge transfer transitions with large oscillator strengths based on the ground state calculated molecular orbital contributions.


KEY WORDS: Phenanthroline, TD-DFT, Photoluminescence, Stokes shift, 1,10-phenanthroline-5,6-dione, Imidazo[4,5-f][1,10]phenanthroline


Bull. Chem. Soc. Ethiop. 2017, 31(1), 137-147. 

AJOL African Journals Online