title: The different electronic natures displayed by the alkylthio groups in simple and higher conjugated aniline systems.
abstract: Systematic studies based on 1H NMR and 13C NMR indicated that the alkylthio group behaves as a weak electron-withdrawing group in a simple aniline system like 2-butylthioaniline, while the same alkylthio group clearly acted as a resonance electron-donating group in higher conjugated aniline trimer systems, like butylthio-substituted PDA (mono-PDA) and dibutylthio-substituted PDA (2,6-diPDA). The formation of 2,6-diPDA as the major byproduct during the preparation of mono-PDA from PDI and butane-1-thiol provided additional support for the resonance electron donating nature of the butylthio group in these aniline trimer systems. Furthermore, CV studies also clearly indicated that the redox potential E degrees (vs. SCE) of the aniline trimer systems decreased with the increase in the number of butylthio groups, further confirming the electron-donating nature of the butylthio group in these higher conjugated trimer systems.
authors.affiliation: Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan ROC. cchan@mx.nthu.edu.tw
authors.forename: Chien-Chung
authors.initials: CC
authors.lastname: Han
authors.forename: R
authors.initials: R
authors.lastname: Balakumar
authors.forename: D
authors.initials: D
authors.lastname: Thirumalai
authors.forename: Ming-Tsu
authors.initials: MT
authors.lastname: Chung