N-Phenylfluorubine: one functional dye – chromophor, fluorophor, electron-acceptor and more

Abstract

We are presenting a new derivative of the fluorubine family which exhibits highly fluorescent activity. 5-Phenyl-dihydro[5,6,7,12,13,14]-hexaazapentacene was synthesized via two subsequent cyclization reactions starting from commercially available starting materials. Its properties were studied intensively via UV-vis and fluorescence spectroscopy, as well as cyclic voltammetry and quantum chemical calculations. Furthermore, we found a strong pH-sensitivity, which influences the photo- and electrochemical properties heavily. Thereby, it is possible to tune its properties from an electron-rich donor to a highly electron-deficient acceptor material.