En Route to Stimuli-Responsive Boron-, Nitrogen-, and Sulfur-Doped Polycyclic Aromatic Hydrocarbons.

Abstract

Replacing both meso carbon atoms of the polycyclic aromatic hydrocarbon (PAH) bisanthene by boron atoms creates an efficient blue fluorophore with a strong electron-accepting character. The corresponding meso-B,S-doped bisanthene exhibits a solvent-dependent green-to-orange photoluminescence and undergoes a reversible reduction at E1/2 =-2.06 V (vs. FcH/FcH(+) ). After oxidation of the sulfur atom, the resulting sulfoxide emits in the blue range of the spectrum, shows only negligible solvatochromism, and a reversible redox transition at E1/2 =-1.74 V. Several related B, N- and B, S-containing PAHs have been prepared following the same modular synthetic procedure and are also described herein. In order to systematically compare their optoelectronic properties, all products have been investigated by cyclic voltammetry as well as UV/Vis absorption/emission spectroscopy.