1352822-10-6Relevant articles and documents
Delineating poly(aniline) redox chemistry by using tailored oligo(aryleneamine)s: Towards oligo(aniline)-based organic semiconductors with tunable optoelectronic properties
Shao, Zhecheng,Rannou, Patrice,Sadki, Said,Fey, Natalie,Lindsay, David M.,Faul, Charl F. J.
supporting information; experimental part, p. 12512 - 12521 (2011/12/15)
The simple and elegant Buchwald-Hartwig cross-coupling reaction has been used to synthesise a designed range of new aniline-based tetramers in one step, and without the need for protecting groups. Variation of the central aromatic ring has provided the opportunity to carefully tune the optoelectronic properties in this series, thus enabling a structure-activity relationship study by using a range of photophysical and electrochemical techniques. As a result, the long-proposed sequences of electron-electron (EE) and electron-chemical (EC) processes that support the complex redox and proton-transfer reactions involved in the well-known switching of redox states of poly- and oligo(aniline)s are revealed here for the first time. We also present the initial results from time-dependent DFT calculations to clarify the optoelectronic behaviour of these oligomers. The dc-conductivity measurements of conducting thin films of this series, doped with the prototypical poly(aniline) protonating agent d,l-camphor-10-sulfonic acid (CSA), externally plasticised with triphenyl phosphate (TPP), and processed from m-cresol (MC) solutions, are also presented. Aniline black, blue, orange and red! The Buchwald-Hartwig cross-coupling reaction is used to synthesise a range of new aniline-based tetramers with carefully tunable optoelectronic properties (see figure; EB=emeraldine base; PANI=poly(aniline)). The long-proposed sequences of electron-electron and electron-chemical processes that support the complex redox and proton-transfer reactions involved in the switching of redox states of poly- and oligo(aniline)s are revealed for the first time. Copyright
