Crystal Engineering and Photophysical Properties of Phenyl-Pyrenoimidazole Systems

• DOI: 10.1021/acs.cgd.9b01443
• Publication Date: 2020-01-30T19:54:53Z
• Authors: Zahra A. Tabasi; Joshua C. Walsh; Graham J. Bodwell; David W. Thompson; Yuming Zhao
• Keywords: Synthon; Moiety; Crystal Engineering; Polar effect; Condensation reaction

A series of π-conjugated phenyl-pyrenoimidazole (Py-Im) systems were synthesized through a one-pot condensation reaction between 4,5-pyrenedione and various benzaldehyde derivatives. The single crystal structures these Py-Im compounds determined, the results showed that Py-Ims can serve as versatile supramolecular synthons for formation diverse solid-state structures, ranging from linear hydrogen bonded networks to complex helical layered π–π stacking assemblies. crystallographic exhibit correlation nature substituent groups attached systems, while dominant intermolecular forces dictate their packing be reasonably accounted by molecular electrostatic potential analysis. Photophysical properties derivatives examined UV–vis absorption fluorescence spectroscopy. Our studies disclosed weak-to-moderate electron-donating/withdrawing have insignificant effects, but strongly electron-withdrawing greatly alter photophysical enhanced proton-exchange processes taking place on imidazolyl moiety.