Home
Resources
Publications
Highly Charged Cations From N,N,N',N'-tetrakis(4-aminophenyl)benzidine and Its N,N,N',N'-tetrakis(4-methoxyphenyl)-substituted Homologue Studied by Thin-Layer in Situ Electron Spin resonance/UV-vis-NIR Spectroelectrochemistry

Highly Charged Cations From N,N,N',N'-tetrakis(4-aminophenyl)benzidine and Its N,N,N',N'-tetrakis(4-methoxyphenyl)-substituted Homologue Studied by Thin-Layer in Situ Electron Spin resonance/UV-vis-NIR Spectroelectrochemistry

Martin Matis, Peter Rapta, Vladimír Lukes, Horst Hartmann, Lothar Dunsch

J Phys Chem B. 2010 Apr 8;114(13):4451-60.

PMID: 20225810

Abstract:

The redox behavior of N,N,N',N'-tetrakis(4-aminophenyl)benzidine (A) and its N,N,N',N'-tetrakis(4-methoxyphenyl)-substituted analogue (B) was studied in detail by a new designed in situ thin layer electron spin resonance (ESR)/UV-vis-NIR spectroelectrohemical cell. The spectroelectrochemical studies of cation radicals, dications, and tetracations indicate a strong difference in stability of higher ions of two model compounds with different phenyl substitution. In cyclovoltammetry the small peak separation of the first two oxidation peaks for both compounds points to a small energetic difference in the first two electron transfers, while the peak separation of the second and third peak is quite large. A well resolved ESR spectrum of the B(*+) cation radical with dominating splittings from two nitrogen atoms is observed and an ESR silent product was determined at the third oxidation peak for both compounds, confirming the formation of a tetracation by a two electron transfer at the third voltammetric peak. In contrast to structure A a more complex redox behavior was found for B under voltammetric cycling. The reaction mechanism indicates the transformation of B in a new product P with a carbazole moiety. This compound can form a highly stabilized cation radical P(*+). A theoretical study based on density functional theory calculations has clarified the role of charging in changes to the structures of both triarylamine derivatives A and B.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP122738210	N,N,N′,N′-Tetrakis(4-methoxyphenyl)benzidine		122738-21-0	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: