Synthesis of a highly luminescent three-dimensional pyrene dye based on the spirobifluorene skeleton.

We have synthesized a highly luminescent (log e > 5.0, F > 0.9) pyrene dye based on a spirobifluorene skeleton [2,2',7,7'-tetrakis(7-tert-butyl-1-pyrenyl)-9,9'-spirobi[9H-fluorene; 4-PySBF]. The use of spirobifluorene prevents fluorescence quenching by intramolecular energy transfer and/or electron transfer among the chromophores in the excited state. The emission spectra of 4-PySBF exhibited a red shift of 20 nm in comparison to a model compound [9,9'-dioctyl-2,7-bis(7-tert-butyl-1-pyrenyl)-9H-fluorene; 2-PyF], but its UV-Vis spectrum remained unchanged.