Triarylamine

In chemistry, a triarylamine has the formula NAr₃ where Ar is any of several aryl groups. The parent member is triphenylamine. Triarylamines are of interest as components of molecular electronics as well as some dyes.^[1]

Preparation and structure

Triarylamines can be produced by arylation of diarylamides with aryl iodides:^[2]

Ar₂NLi + Ar'I → Ar₂Ar'N + LiI

Buchwald-Hartwig coupling methods have also been applied.^[3]

Structure of the cation ((C₆H₅)₂N)₂C₆H+4. The phenyleneC-N distances are 1.36 pm vs 143 pm in the neutral parent.^[4]

Many hundreds of triarylamines have been prepared. In some cases, their radical cationic derivatives have been characterized by X-ray crystallography.

References

^ Wang, Jiayu; Liu, Kuan; Ma, Lanchao; Zhan, Xiaowei (2016). "Triarylamine: Versatile Platform for Organic, Dye-Sensitized, and Perovskite Solar Cells". Chemical Reviews. 116 (23): 14675–14725. doi:10.1021/acs.chemrev.6b00432. PMID 27960267.
^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, p. 876, ISBN 978-0-471-72091-1
^ Hartwig, John F. (1998). "Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and Mechanism". Angewandte Chemie International Edition. 37 (15): 2046–2067. doi:10.1002/(sici)1521-3773(19980817)37:15<2046::aid-anie2046>3.0.co;2-l. PMID 29711045.
^ Szeghalmi, Adriana V.; Erdmann, Marco; Engel, Volker; Schmitt, Michael; Amthor, Stephan; Kriegisch, Volker; Nöll, Gilbert; Stahl, Rainer; Lambert, Christoph; Leusser, Dirk; Stalke, Dietmar; Zabel, Manfred; Popp, Jürgen (2004). "How Delocalized is N , N , N , N -Tetraphenylphenylenediamine Radical Cation? An Experimental and Theoretical Study on the Electronic and Molecular Structure". Journal of the American Chemical Society. 126 (25): 7834–7845. doi:10.1021/ja0395386. PMID 15212531.

[1] Wang, Jiayu; Liu, Kuan; Ma, Lanchao; Zhan, Xiaowei (2016). "Triarylamine: Versatile Platform for Organic, Dye-Sensitized, and Perovskite Solar Cells". Chemical Reviews. 116 (23): 14675–14725. doi:10.1021/acs.chemrev.6b00432. PMID 27960267.

[2] Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, p. 876, ISBN 978-0-471-72091-1

[3] Hartwig, John F. (1998). "Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and Mechanism". Angewandte Chemie International Edition. 37 (15): 2046–2067. doi:10.1002/(sici)1521-3773(19980817)37:15<2046::aid-anie2046>3.0.co;2-l. PMID 29711045.

[4] Szeghalmi, Adriana V.; Erdmann, Marco; Engel, Volker; Schmitt, Michael; Amthor, Stephan; Kriegisch, Volker; Nöll, Gilbert; Stahl, Rainer; Lambert, Christoph; Leusser, Dirk; Stalke, Dietmar; Zabel, Manfred; Popp, Jürgen (2004). "How Delocalized is N , N , N , N -Tetraphenylphenylenediamine Radical Cation? An Experimental and Theoretical Study on the Electronic and Molecular Structure". Journal of the American Chemical Society. 126 (25): 7834–7845. doi:10.1021/ja0395386. PMID 15212531.

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