Fluorescence response of pyridinyl- and/or dibutylaniline-capped 2,6,9,10-tetravinylanthracenes to metal ions

•A series of cruciforms 1–6 have been synthesized.•Cruciforms 1–6 exhibit spatially separated frontier molecular orbital features.•Cruciforms 1–6 exhibit strong intermolecular charge transfer effect.•The Cu2+ and Zn2+ can red-shift, blue-shift or quench the fluorescence emissions.

The solution photophysical properties of a series of dibutylaniline- and/or pyridine-containing 2,6,9,10-tetrarylvinylanthracene cruciforms with and without metal ions have been determined. The results show that the dibutylaniline-containing cruciforms show stronger intermolecular charge transfer and obviously red-shifted emission spectra than the only pyridine-containing ones, and fluorescence responses of these cruciforms to select several metal ions are also different. The alkali K+, alkaline-earth Mg2+ and Ca2+ hardly affect the emission behavior, but the transition Cu2+ and Zn2+ could red-shift, blue-shift or quench the fluorescence emissions, depending on the nature of end groups. The fluorescence responsive behaviors of the different cruciforms to metal ions are explained qualitatively through their spatially separated frontier molecular orbital (FMO) features and coordination-induced FMO changes. These findings suggest that these anthracene-centered cruciforms could be promising functional scaffolds selectively for differential transition metal sensor arrays.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide