101-70-2Relevant articles and documents
Comparative analysis of triarylamine and phenothiazine sensitizer donor units in dye-sensitized solar cells
Chiykowski, Valerie A.,Lam, Brian,Du, Chuan,Berlinguette, Curtis P.
, p. 2367 - 2370 (2017)
A homologous set of dyes that differ only in the donor fragments, namely phenothiazine (PTZ) and triarylamine (TPA) units, were evaluated in dye-sensitized solar cells (DSSCs). The novel PTZ-based dye differs from the TPA-based dye in that it contains a sulfur bridge that planarizes two aromatic rings and enables higher dye loading and higher stability in the oxidized form. These positive features notwithstanding, the superior absorptivity of devices sensitized by TPA-based dyes resulted in significantly higher power conversion efficiencies (PCEs) than those sensitized by PTZ-based dyes.
Copper-catalyzed amination of aryl halides: Single-step synthesis of triarylamines
Kelkar, Ashutosh A.,Patil, Nandkumar M.,Chaudhari, Raghunath V.
, p. 7143 - 7146 (2002)
A simple and efficient methodology for the synthesis of triarylamines in a single step has been demonstrated using a ligand-free CuI catalyst and potassium tertiary butoxide as the base. Use of chelating ligands leads to the formation of triarylamine derivatives selectively (95% yield) with high catalytic activity.
A simple access to symmetric diarylamines via copper(II)-catalyzed coupling of aqueous ammonia with arylboronie acids
Zhou, Changfeng,Chen, Fan,Yang, Dongpeng,Jia, Xiaofei,Zhang, Lixue,Cheng, Jiang
, p. 708 - 709 (2009)
A simple and efficient CuII-catalyzed coupling reaction of arylboronic acids with aqueous ammonia under air is described. The reaction was conducted under atmospheric pressure and no additional ligand was required. Benzoic acid was added to tune the basicity of the reaction system. Copyright
Design and synthesis of stable triarylamines for hole-transport applications
Zhao, Hongda,Tanjutco, Christine,Thayumanavan, S.
, p. 4421 - 4424 (2001)
Three new tetrakis(triarylamino)methanes have been designed and synthesized. These triarylamines have been shown to exhibit high glass-transition temperatures and optimal oxidation potential for achieving efficient OLEDs. The para-position of the aryl rings is blocked with electron-donating t-butyl or methoxy groups, which enhances the radical cation stability of these molecules - a highly desirable quality for hole transporters.
One-pot synthesis of symmetrical and asymmetrical diphenylamines from guanidines with aryl iodide using Cu/Cu2O nanocatalyst
Chaurasia, Shivkumar R.,Bhanage
, (2020)
This work reports the selective one-pot synthesis of symmetrical and asymmetrical amines from guanidines as ammonia surrogate. The use of guanidine as ammonia source will eliminate the need of handling liquid ammonia. The reaction was performed using Cu/Cu2O nanocatalyst under ligand-free condition. The synthesized catalyst was characterized by a various technique like XRD, FEG-SEM, HRTEM and XPS. The different diphenylamines are produced in good to very good yields. Recyclability study of catalyst shows that up to five cycles there is no significant loss in its activity.
Reactivity of tris(trimethylsilyl)silane toward diarylaminyl radicals
Varlamov,Denisov,Chatgilialoglu
, p. 6317 - 6322 (2001)
Absolute rate constants for the reaction of tri-tert-butylphenoxyl radical (ArO·) with (TMS)3SiH were measured spectrophotometrically in the temperature range 321-383 K. Rate constants for the hydrogen abstraction from (TMS)3SiH by diarylaminyl radicals of type (4-X-C6H4)2N· were determined by using a method in which the corresponding amines catalyze the reaction of ArO· with (TMS)3SiH. At 364.2 K, rate constants·are in the range of 2-50 M-1 s-1 for X = H, CH3, CH3O, and Br, whereas the corresponding value for ArO· is 3 orders of magnitude lower. A common feature of these reactions is the low preexponential factor [log(A/M-1 s-1) of 4.4 and 5.2 for ArO· and Ph2N·, respectively], which reflects high steric demand in the transition state. A semiempirical approach based on intersecting parabolas suggests that the observed reactivity is mainly related to the enthalpy of the reaction and allowed to estimate activation energies for the reaction of (4-X-C6H4)2N· and ArO· radicals with a variety of silicon hydrides.
Electron Push-Pull Effects in 3,9-Bis(p-(R)-diphenylamino)perylene and Constraint on Emission Color Tuning
Ahn, Mina,Kim, Min-Ji,Wee, Kyung-Ryang
, p. 12050 - 12057 (2019)
A series of perylene-based donor-acceptor-donor (D-A-D) compounds, 3,9-bis(p-(R)-diphenylamino)perylene (R: CN (2a), F (2b), H (2c), Me (2d), and OMe (2e)), was synthesized using 3,9-dibromoperylene with p-(R)-diphenylamine, and the intramolecular charge transfer (ICT) on the D-A-D system with regard to the electron push-pull substituent effect was investigated. By introducing various p-(R)-diphenylamine derivatives with electron-donating or electron-withdrawing R groups, the energy band gaps of the D-A-D compounds were systematically controlled and the emission colors were efficiently tuned from green to red. As expected, the steady state emission spectra of all D-A-D compounds were observed, as well as the emission color controlled, depending on the Hammett substituent constants (σp). In the Lippert-Mataga plots, a different charge-transfer character was observed depending on the electron push-pull substitution, which showed gradually increased ICT characters from the electron-withdrawing to donating substitution. However, exceptionally, the strong electron-withdrawing group of CN-substituted 2a did not correlate with the other R group compounds. From the experimental data and density functional theory calculations, we assume that there is a constraint on emission color tuning to generate higher energy of blue emission in the D-A-D molecular system, due to the reverse charge-transfer property caused by the strong electron-withdrawing group.
Electron Push-Pull Effects on Intramolecular Charge Transfer in Perylene-Based Donor-Acceptor Compounds
Ahn, Mina,Kim, Min-Ji,Cho, Dae Won,Wee, Kyung-Ryang
, p. 403 - 413 (2021)
A series of asymmetric donor-acceptor (D-A) perylene-based compounds, 3-(N,N-bis(4′-(R)-phenyl)amino)perylene (Peri-DPA(R)), were successfully prepared to explore their intramolecular charge transfer (ICT) properties. To induce ICT between the donor and acceptor, diphenylamine (DPA) derivatives (electron donor units) with the same functional groups (R = CN, F, H, Me, or OMe) at both para positions were linked to the C-3 position of perylene to produce five Peri-DPA derivatives. A steady-state spectroscopy study on Peri-DPA(R)s exhibited a progressively regulated ICT trend consistent with the substituent effect as it progressed from the electron-withdrawing group to the electron-donating group. In particular, a comparative study using a D-A-D (donor-acceptor-donor) system demonstrated that not only the electron push-pull substituent effect but also subunit combinations influence photophysical and electrochemical properties. The different ICT characters observed in Lippert-Mataga plots of D-A(CN) and D-A-D(CN) (CN-substituted D-A and D-A-D) led to the investigation on whether ICT emission of two systems with differences in subunit combinations is of the same type or of a different type. The femtosecond transient absorption (fs-TA) spectroscopic results provided direct evidence of ICT origin and confirmed that D-A(CN) and D-A-D(CN) exhibited the same transition mix of ICT (from donor to acceptor) and reverse ICT (rICT, from arylamine to CN unit). Density functional theory (DFT)/TD-DFT calculations support the presence of ICT for all five compounds, and the experimental observations of rICT presented only for CN-substituted compounds.
A novel panchromatic shutter based on an ambipolar electrochromic system without supporting electrolyte
Wu, Jung-Tsu,Liou, Guey-Sheng
, p. 2619 - 2622 (2018)
Two triphenylamine derivatives, N,N,N′,N′-tetrakis(4-methoxyphenyl)-1,4-phenylenediamine TPPA and N,N,N′,N′-tetrakis(4-methoxyphenyl)-1,1′-biphenyl-4,4′-diamine TPB, were successfully prepared and combined with HV to fabricate the electrochromic device as a panchromatic shutter for the application of transparent display. The obtained electrochromic device exhibits exceptional novel electrochromic properties, including enhanced color contrast, switching time, and long-term stability. Furthermore, it is worth mentioning that the most important contribution of this ambipolar system approach is that no supporting electrolyte is added into the device.
A new carbazole-based hole-transporting material with low dopant content for perovskite solar cells
Wang, Jiang,Chen, Yu,Li, Fusheng,Zong, Xueping,Guo, Jinlin,Sun, Zhe,Xue, Song
, p. 673 - 680 (2016)
A new carbazole-based hole-transporting material incorporating a 3,3′-biphenyl central core has been synthesized via a facile route. A reference compound without carbazole moiety was also prepared. Their geometric structures, thermal stability and photovoltaic properties were investigated. This new carbazole-based material exhibits a high glass transition temperature (167.8 °C) and a suitable highest occupied molecular orbital level well-matched with CH3NH3PbI3 perovskite. A low doping content of 4-tert-butylpyridine (120 mM) is observed for the best performance of perovskite solar cell in conjunction with a carbon counter electrode. The device achieves a power conversion efficiency of 4.53% under illumination of 100 mW cm-2. The performance is much better than that of the reference compound (0.19%), and comparable to that of spiro-OMeTAD at the same dopant level (5.10%). The results indicate the carbazole-based material is a promising class of hole-transporting materials for perovskite solar cells.
Cathodic reduction of diazonium salts in aprotic medium
Barba, Fructuoso,Batanero, Belen,Tissaoui, Khalil,Raouafi, Noureddine,Boujlel, Khaled
, p. 973 - 976 (2010)
Cathodic reduction of diazonium salts in acetonitrile led to the formation of azobenzenes, in good to moderate yields, and diarylamines as minoritary products. The reactions were carried out at the second reduction potential of the diazonium salts, involving aryl anions in the formation of the products.
Novel CuI/tributyl phosphine catalyst system for amination of aryl chlorides
Patil, Nandkumar M.,Kelkar, Ashutosh A.,Nabi, Zahid,Chaudhari, Raghunath V.
, p. 2460 - 2461 (2003)
A simple and efficient methodology for the synthesis of triarylamines from aryl chlorides in a single step has been demonstrated using a novel Cul/ tributyl phosphine catalyst system with high activity and selectivity (80-87% yield).
NaOTs-promoted transition metal-free C-N bond cleavage to form C-X (X = N, O, S) bonds
Chen, Wei,Liu, Sicheng,Liu, Tingting,Majeed, Irfan,Ye, Xiaojing,Zeng, Zhuo,Zhang, Yuqi,Zhu, Yulin
supporting information, p. 8566 - 8571 (2021/10/20)
Multifunctional transformation of amide C-N bond cleavage is reported. The protocol applies to benzamide, thioamide, alcohols, and mercaptan under similar reaction conditions catalyzed by NaOTs. It is noteworthy that NaOTs can not only be recycled and reused for up to three cycles without significant loss in catalytic activity, but also catalyze gram-grade reactions. This study provides a novel solution with mild conditions and a simple procedure for transformation of multiple amides.
COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND A ELECTRONIC DEVICE THEREOF
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Paragraph 0103; 0106-0109, (2021/06/22)
In the present invention, provided is a novel compound capable of improving luminance efficiency, stability, and service life of an element, an organic electronic element using the same, and an electronic device thereof. By using the compound of the present invention, high luminance efficiency, low driving voltages, and high heat resistance of the element can be achieved, and color purity and service life of the element can be greatly improved.
