Synthesis, Crystal Structure and Optical Properties of Novel 1,10-Phenanthroline Derivatives Containing 2,6-Diisopropylphenoxy Substituents

Abstract

Two phenanthroline derivatives, 2-(2,6-diisopropylphenoxy)-9-phenyl-1,10-phenanthroline and 2,9-bis(2,6-diisopropylphenoxy)-1,10-phenanthroline, were synthesized. The unsymmetrical derivative was obtained in high yield through a sequence combining Suzuki coupling and nucleophilic substitution. The crystal structures of both compounds were determined by single-crystal X-ray diffraction and examined by Hirshfeld surface analysis, which outlined the main intermolecular interactions responsible for the packing. The optical properties were studied by UV–Vis absorption and fluorescence spectroscopy in different solvents. The unsymmetrical compound showed stronger intramolecular charge transfer and more pronounced solvatochromism, while the symmetrical analog had a higher fluorescence quantum yield and longer excited-state lifetime. These results demonstrate the role of substitution symmetry in controlling molecular organization and photophysical properties of phenanthroline derivatives, with relevance to sensing and optoelectronic applications.