Borylated arylisoquinolines: photophysical properties and switching behavior of promising tunable fluorophores

Chemistry. 2013 May 17;19(21):6650-61. doi: 10.1002/chem.201203887. Epub 2013 Mar 28.


A series of nine borylated arylisoquinolines has been prepared with systematic variation in their electronic properties and their photophysical properties were investigated. The color of their fluorescence can be finely tuned by changing the properties of the aryl moiety, which is involved in internal-charge-transfer processes. For example, methoxy-substituted compound 5 showed an intense green emission, whereas dimethylamino-substituted compound 6 showed an orange-red emission. These new fluorophores were tested for their potential as molecular switches with external ionic stimuli, such as protons and fluoride ions. On the one hand, protonation of the isoquinoline moiety led to fluorescence enhancement for compounds that showed weak charge transfer and fluorescence quenching for compounds that showed strong charge transfer. On the other hand, the formation of ate complexes with fluoride led to strong fluorescence quenching in all of the investigated cases.