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Perylenetetracarboxylic diimide derivatives bearing 2- or 4-peripheral pyrrole pendants could be efficiently crosslinked to form an insoluble film either by electropolymerization or visible light induced oxidative photopolymerization of the pyrrole units.

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Perylenetetracarboxylic diimide (PDI) derivatives bearing two or four peripheral pyrrole pendants (PDI-nPy, n=2 or 4) are cross-linkable materials by electro/phototreatment. In this paper, we introduce a new posttreatment technique to produce an insoluble film. Unlike the common solution-phase electrochemical deposition, we first spin-coated PDI-nPy on an electrode and then electrotreated the coated surface in a monomer-free electrolyte solution. This method gives the film a smooth surface with no granules, while the common method induces a rough film with a lot of granules. The post electrochemical treatment also provides a merit of higher resolution in a patterning process on a specific metal electrode. As one of the applications, we carried out an electrochromic study on the posttreated PDI-4Py film. It turned purple (lambdamax=590 nm) and sky blue (lambdamax=797 nm) at 0 and -1.9 V vs Ag/Ag+, respectively. We believe this method will broaden the patterning concept with the desired film morphology and resolution using PDI on a specific electrode.