Direct synthesis of diamine radical cations in crystalline form proceeding through oxidation of triphenylamine followed by the formation of a new C−N bond is reported. Although the oxidative coupling of triphenylamine is well studied, diamine products are rarely captured in their radical cation state. The neutral diamine most frequently obtained from this reaction pathway is N,N,N’,N’‐tetraphenylbenzidine. Herein, the capture of radical cations of diamines in crystalline form in one step starting with neutral triphenylamine was demonstrated, and the formation of two products (the radical cations of N,N,N′,N′‐tetraphenyl‐1,4‐benzenediamine or N,N,N′,N′‐tetraphenylbenzidine) depending on the oxidizing agent used was observed. The radical species are characterized by single‐crystal X‐Ray diffraction, electron paramagnetic resonance spectroscopy, and optical spectroscopy.
- Award ID(s):
- 1801317
- NSF-PAR ID:
- 10172710
- Date Published:
- Journal Name:
- RSC Advances
- Volume:
- 10
- Issue:
- 34
- ISSN:
- 2046-2069
- Page Range / eLocation ID:
- 19861 to 19866
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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Abstract A series of
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- Free Publicly Accessible Full Text
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Accepted Manuscript1.0
- Journal Article:
- https://doi.org/10.1039/D0RA04379F
