Organic high-spin systems of oligoarylamines: Properties of tetraaryl- m-phenylendiamine oligocations as examined by electron transfer stopped-flow method

Triarylamine-based diamines and triamines were synthesized as precursors of positvely charged high-spin systems. Their electrochemical and spectroscopic prooerties were examined. Three types of N, N, N′, N′-tetraaryl-1,3-phenylenediamines with bromo atoms as protecting groups were designed and synth...

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Published in:Polyhedron 2005-11, Vol.24 (16), p.2116-2120
Main Authors: Yano, Masafumi, Nakanishi, Yasuyuki, Matsushita, Kosuke, Tatsumi, Masakazu, Oyama, Munetaka, Sato, Kazunobu, Takui, Takeji
Format: Article
Language:English
Subjects:
Bromination
Charged high-spin systems
Electrochemical methods
Electron transfer stopped-flow method
Oligoarylamines
Stable open-shell systems
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Summary:Triarylamine-based diamines and triamines were synthesized as precursors of positvely charged high-spin systems. Their electrochemical and spectroscopic prooerties were examined. Three types of N, N, N′, N′-tetraaryl-1,3-phenylenediamines with bromo atoms as protecting groups were designed and synthesized. Electrochemical and novel electron transfer stopped-flow (ETSF) methods were invoked for characterizing the absorption spectra of the corresponding short-lived mono- and dicationic states. Useful molecular design rules for stabilizing the dicationic states of N, N, N′, N′-tetraaryl-1,3-phenylenediamines as precursors for positively charged high-spin systems were elucidated. An extended system, 3,3′-bis(diphenylamino)triphenylamine in the tricationic state with four bromo groups was also examined, being confirmed to give a ground-state triplet dication by ESR spectroscopy.
ISSN:0277-5387
DOI:10.1016/j.poly.2005.03.027