Beilstein Journal of Organic Chemistry 2016-01-01

Synthesis and fluorosolvatochromism of 3-arylnaphtho[1,2-b]quinolizinium derivatives.

Phil M Pithan, David Decker, Manlio Sutero Sardo, Giampietro Viola, Heiko Ihmels

Index: Beilstein J. Org. Chem. 12(1) , 854-62, (2016)

Full Text: HTML

Abstract

Cationic biaryl derivatives were synthesized by Suzuki-Miyaura coupling of 3-bromonaphtho[1,2-b]quinolizinium bromide with arylboronic acids. The resulting cationic biaryl derivatives exhibit pronounced fluorosolvatochromic properties. First photophysical studies in different solvents showed that the emission energy of the biaryl derivatives decreases with increasing solvent polarity. This red-shifted emission in polar solvents is explained by a charge shift (CS) in the excited state and subsequent solvent relaxation. Furthermore, the polarity of protic polar and aprotic polar solvents affects the emission energy to different extent, which indicates a major influence of hydrogen bonding on the stabilization of the ground and excited states.