Journal of Electroanalytical Chemistry, Vol.444, No.1, 101-112, 1998
Electrochemical behaviour of different binaphthalene crown ethers. Part 2 : novel strategy based on in situ removable bromine atom protecting groups for the electrosynthesis of polybinaphthalenes bearing perylene crown ethers as potentially redox switchable macromolecular hosts
The substitution of the 6 and 6' position of binaphthalene derivatives efficiently prevents their anodic polymerization. Instead, an intramolecular coupling reaction occurs leading to perylenes. Accordingly, the anodic oxidation of a bis-binaphthalene crown ether in which one of the binaphthalene subunits has thus been protected by two bromine atoms leads to the deposition of an electroactive polymer film onto the electrode surface. By proper choice of the reaction conditions, this polymerization reaction can be accompanied by the formation of perylene subunits in the pendant crown ethers. Subsequent in situ cathodic removal of the bromine atoms has been achieved, leading to the parent conducting polymer possessing perylene moieties.