Facile synthesis, crystal structures, and high-spin cationic states of all-para-brominated oligo(N-phenyl-m-aniline)s

Akihiro Ito; Haruhiro Ino; Kazuyoshi Tanaka; Katsuichi Kanemoto; Tatsuhisa Kato

doi:10.1021/jo0160571

Facile synthesis, crystal structures, and high-spin cationic states of all-para-brominated oligo(N-phenyl-m-aniline)s

J Org Chem. 2002 Jan 25;67(2):491-8. doi: 10.1021/jo0160571.

Authors

Akihiro Ito¹, Haruhiro Ino, Kazuyoshi Tanaka, Katsuichi Kanemoto, Tatsuhisa Kato

Affiliation

¹ Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.

PMID: 11798322
DOI: 10.1021/jo0160571

Abstract

Syntheses of both the dimer (3) and the trimer (4) of all-para-brominated poly(N-phenyl-m-aniline)s (2c) were achieved in a one-pot procedure from the parent nonbrominated oligomers and benzyltrimethylammonium tribromide [(BTMA)Br(3)]. An X-ray crystallographic analysis revealed that 4 has a U-shaped structure, suggesting that 2c easily adopts helical structures. Furthermore, the redox properties were investigated by the UV-vis and EPR measurements. It was confirmed that the both 3 and 4 can be oxidized into the dications 3(2+) and 4(2+) with triplet spin-multiplicity.