Thermal Insolubilization of Electrically N-Doped Films Achieved Using 7-Alkoxy-benzocyclobutene-substituted Fullerene and Dopant Molecules.

Insoluble electrically n-doped fullerene-containing films have been obtained by thermal annealing of a fullerene compound and a 1,3-dimethyl-2,3-dihydro-1H-benzo[d]imidazole n-dopant moiety, both of which are functionalized with a 7-butoxybenzocyclobutene group. The covalent tethering and electrical doping reactions are studied by mass spectrometry as well as electron paramagnetic resonance. Optical absorption spectra on BBCB-N-DMBI-H-doped BBCBP indicate films heated at 150 °C for 10 min are unaffected by immersion for 10 min in ortho-dichlorobenzene. Although films containing a 10 mol % loading of the dopant showed electrical conductivity values of 1.1 × 10-5 ± 3.4 × 10-7 S cm-1 prior to heating, the thermal insolubilization process led to values around two orders-of-magnitude lower. However, the thermal insolubilization also leads to immobilization of the dopant molecule and the corresponding cation, reducing their ability to diffuse into an adjacent layer of a stronger electron acceptor.