65181-78-4Relevant articles and documents
Electron Spin Resonance Spectroscopic Study of Electronic Charge Transport in an Aromatic Diamine
Veregin, Richard P.,Harbour, John R.
, p. 6231 - 6237 (1990)
Electron spin resonance (ESR) spectra have been obtained for the radical cation of N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diamine (TPD) in dichloromethane solution, in solid amorphous films, and in TPD/polycarbonate films doped with tris(p-bromophenyl)ammonium hexachloroantimonate or HNO3.By use of ESR the mediation of electronic charge (hole) transport via the TPD+ radical cation has been observed in the TPD films in the absence of an applied field.Arrhenius activation parameters were calculated for charge transport from the ESR data, giving EA = 10 +/- 2 kJ/mol Α = (1.7 +/- 1) * 1010 s-1, and a rate constant at 300 K of (3.1 +/-1) * 108 s-1.The value of EA is one-half that from time-of-flight (TOF) measurements extrapolated to zero field, while the rate constant is a factor of 10 smaller, and Α is a factor of 1000 smaller.The differences can be understood in terms of the compensation effect due to the presence of residual solvent, and the ion pairing of an TPD+ ions with dopant counterions.In TPD/polycarbonate films the rate of hole transport is too slow to produce significant changes in the ESR spectrum.The rate of charge transport is thus less than 2*108 s-1 in these films, consistent with TOF data.In dichloromethane solution, an EA of 9.8 kJ/mol was observed with ESR.Extrapolating the solution data to solid TPD gives a hole transport rate of 9.75 * 109 s-1, a factor of 3 higher than that from TOF data.The lower Ea and higher rate in dichloromethane solution are consistent with the effect of the higher dielectric constant compared to an TPD film.This suggests that the rate-determing step for hole transport is the same in solution as it is in the solid state.
In-situ generation and analysis of charge transfer materials using an OTTLE cell and resonance Raman scattering
Littleford, Rachael E.,Paterson, Michael A. J.,Low, Paul J.,Tackley, Daniel R.,Jayes, Linda,Dent, Geoffrey,Cherryman, Julian C.,Brown, Bev,Smith, W. Ewen
, p. 3257 - 3263 (2004)
Poly(aryl)amine based charge transfer materials (CTMs) are essential components in a range of present and future technologies, from the Xerox process to display devices based upon light emitting polymers (LEPs). However, there is a lack of detailed understanding regarding the electronic properties of CTMs in their various neutral and oxidized forms. This paper reports the use of an optically transparent thin layer electrochemical (OTTLE) cell in combination with a Raman microprobe system and DFT calculations to provide information on the molecular and electronic structure of the mono- and di-oxidized derivatives of the classic CTM N,N′-diphenyl-N,N′-bis(3-methylphenyl)(1, 1′-biphenyl)-4,4′-diamine (TPD) and the closely related species N,N′-diphenyl-N,N′-bis(2,4-dimethylphenyl)(1,1′-biphenyl)-4, 4′-diamine (DMTPD). The resonance Raman scattering profile easily discriminates between the monovalent and divalent cations while DFT calculations permit correlation of the observed vibrational frequencies with localized atomic displacements. The cations are best described in terms of a symmetrical (i.e. fully delocalized) structure. The high sensitivity of the method suggests that it should be appropriate for the observation of low concentrations of the various cations generated from TPD type CTMs during device operation.
(DiMeIHeptCl)Pd: A Low-Load Catalyst for Solvent-Free (Melt) Amination
Semeniuchenko, Volodymyr,Sharif, Sepideh,Day, Jonathan,Chandrasoma, Nalin,Pietro, William J.,Manthorpe, Jeffrey,Braje, Wilfried M.,Organ, Michael G.
, p. 10343 - 10359 (2021/07/31)
(DiMeIHeptCl)Pd, a hyper-branched N-aryl Pd NHC catalyst, has been shown to be efficient at performing amine arylation reactions in solvent-free ("melt") conditions. The highly lipophilic environment of the alkyl chains flanking the Pd center serves as lubricant to allow the complex to navigate through the paste-like environment of these mixtures. The protocol can be used on a multi-gram scale to make a variety of aniline derivatives, including substrates containing alcohol moieties.
Method for preparing biphenyl triarylated amine compound by taking carboxyl as guide group, intermediate and preparation method thereof
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, (2018/07/30)
The invention relates to a method for preparing a biphenyl triarylated amine compound by taking carboxyl as a guide group, an intermediate and a preparation method thereof. The intermediate has a structure as shown in the formula, (the formula is shown in the description), wherein R is selected from hydrogen, alkyl with a carbon atom number of 1-10, halogenated alkyl with a carbon atom number of 1-5, alkoxy with a carbon atom number of 1-5 and aryl. The intermediate is prepared from simple and easily available raw materials, and the biphenyl triarylated amine compound prepared by the intermediate is high in purity and yield, so that the production cost of the biphenyl triarylated amine compound can be remarkably reduced, and therefore, the method is very suitable for industrial productionof the biphenyl triarylated amine compound.
Method for producing hydroxytriarylamine (by machine translation)
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Paragraph 0037, (2018/02/24)
PROBLEM TO BE SOLVED: To economically provide arylamines such as triarylamine. SOLUTION: An arylamine compound represented by formula (1) and an aryl compound having a leaving group represented by formula (2): X-Ar2-X1, are subjected to an arylamination reaction in the presence of a basic group, an alkaline metal salt and/or an alkaline earth metal salt, and an iron catalyst to thereby obtain arylamines such as triarylamines. In formula (1), Ar and Ar1are identical or different, and denote a substituted or non-substituted aryl group, and may be ring-condensed; and a denotes 1 or 2. In formula (2), X and X1are identical or different, and denote at least one leaving group selected from the group consisting of H or Br, I, CMs (mesylate), OTf (triflate) and OTs (tosylate), provided that X and X1are not simultaneously H, and have at least one leaving group; and Ar2denotes a substituted or non-substituted aryl group. COPYRIGHT: (C)2012,JPO&INPIT
