Bright, Red Single-Molecule Emitters: Synthesis and Properties of Environmentally Sensitive Dicyanomethylenedihydrofuran (DCDHF) Fluorophores with Bisaromatic Conjugation

A group of new fluorescent dye materials for single-molecule imaging applications, comprised of an amine donor, a pi-system consisting of phenyl and thiophene rings, and a dicyanomethylenedihydrofuran acceptor group have been synthesized. Relative to comparable single-ring compounds, these doubly aromatic conjugated fluorophores have red-shifted absorption and emission, usually accompanied by significantly increased quantum yields. Solvatochromism studies indicate that the photophysical properties of these dyes are sensitive to the solvent polarity and environmental rigidity. Photophysical studies demonstrate that these DCDHF dye materials are strong single-molecule emitters and the total number of detected photons per molecule is among the highest observed thus far for this family of fluorophores.