Work

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

Year: 2025

Type: article

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.

Source: Crystals

DOI: 10.3390/cryst15100883

Authors: Martin Tsvetkov, Rumen Lyapchev, Mihail Kolarski, Bernd Morgenstern, Joana Zaharieva

Institutions: Sofia University "St. Kliment Ohridski", Saarland University

Language: English

Topic: Crystal structures of chemical compounds

Subfield: Inorganic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $2,534

Funder: Universität des Saarlandes