An oligomeric fluorene with pendant TTF units (OFT) was synthesized by the Yamamoto coupling reaction using Ni(COD)(2) as catalyst. The fluorescence spectra of fluorene-TTF (3a) and OFT displayed weak fluorescence intensity because of the photoinduced electron transfer (PET) interaction and energy transfer between the TTF and fluorene, while the fluorescence intensity would enhance significantly after chemical oxidation. The absorption spectra and cyclic voltammetry (CV) showed that an intramolecular interaction existed between the TTF and fluorene moieties in OFT, while in 3a such interaction could not be observed, due to the chain propagation of the fluorene backbone and an enhanced internal charge transfer interaction between the two electroactive moieties. Moreover, the conductivity showed that the doped OFT possessed a higher conductivity (1.4 x 10(-3) S cm(-1)) than the doped 3a (9.8 x 10(-5) S cm(-1)). These results demonstrated that OFT was a good candidate of fluorescence switches and conducting materials.