Cathodic Hydrodefluorination of a π-Conjugated Alternating Copolymer Consisting of 9,9-Dioctylfluorene and Tetrafluorophenylene

Abstract

Fluorine-containing π-conjugated polymers show unique optoelectronic properties because of installed fluorine atoms into their main chains. To manipulate their optoelectronic properties, replacing fluorine atoms with other functional groups or elements by polymer reaction is straightforward. However, polymer reactions applicable to fluorine-containing π-conjugated polymers remain limited to those using nucleophilic aromatic substitution reactions. Here, we report the cathodic hydrodefluorination of a 1,2,4,5-tetrafluorophenylene moieties containing π-conjugated polymer using a platinum (Pt) plate or a zinc (Zn) plate as a working electrode. The use of a Pt plate as a working electrode converts tetrafluorophenylene units to difluorophenylene units and monofluorophenylene units. On the other hand, the use of a Zn plate as a working electrode is found to be effective in suppressing the formation of the monofluorophenylene units. We also demonstrate the facile tuning of the optoelectronic properties of the pristine π-conjugated polymer by the cathodic hydrodefluorination.