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.
Mild method for ullmann coupling reaction of amines and aryl halides
Ma, Dawei,Cai, Qian,Zhang, Hui
, p. 2453 - 2455 (2003)
(Matrix presented) Ullmann-type aryl amination of aryl iodides and aryl bromides in DMSO at 40-90°C gave the corresponding N-arylamines or N,N-diarylamines in good to excellent yields by using either N-methylglycine or L-proline as the ligand.
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.
Squaraine dyes containing diphenylamine group: Effects of different type structures on material properties and organic photovoltaic performances
Yang, Lin,Zhu, Youqin,Wu, Jianglin,Hu, Bin,Pang, Zhenguo,Lu, Zhiyun,Zhao, Suling,Huang, Yan
, (2019)
Four donor-acceptor-donor (D-A-D’) unsymmetrical squaraines (USQs) with different molecular skeletons (XZ-type and YZ-type), containing diphenylamine group with/without methoxy substituent were synthesized as donor materials in bulk-heterojunction (BHJ) organic photovoltaics (OPVs). The introduction of methoxy group in USQs has little different effects on the overall photovoltaic performance. Conversely, the different molecular skeleton types of the USQs have significant influence on their material properties and photovoltaic performances. Compared to BIDPSQ and BIDPOMeSQ with XZ-type molecular skeleton, IDPSQ and IDPOMeSQ with YZ-type molecular skeleton display closer solid-state packing, much lower highest occupied molecular orbital (HOMO) energy level, higher hole mobility and smaller phase separation domain size. Consequently, YZ-type USQs exhibit the most excellent performance with power conversion efficiency (PCE) of ~4%, which is approximately 300% higher than those of XZ-type USQs. Surprisingly, even though IDPSQ and IDPOMeSQ show wide band gaps, the corresponding devices still achieve a highest PCE of ~4%, which is comparable to or even higher than the PCEs of some reported SQ-based devices with low band gaps. These results indicate the YZ-type molecular skeleton and the electron-donating diphenylamine group are very promising to construct highly efficient squaraine donor materials.
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
PEt3-mediated deoxygenative C–N coupling of nitroarenes and boronic acids
Nykaza, Trevor V.,Yang, Junyu,Radosevich, Alexander T.
, p. 3248 - 3252 (2019)
A method for the preparation of aryl- and heteroarylamine products by triethylphosphine-mediated deoxygenative coupling of nitroarenes and boronic acids is reported. This method provides access to an array of functionalized (hetero)arylamine products from readily available starting materials under the action of an inexpensive commercial reagent. The developed triethylphosphine-mediated transformation highlights the capability of organophosphorus compounds to carry out this useful deoxygenative transformation without the necessity of any transition metal additives.
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.
Nickel-catalyzed N-arylation of amines with arylboronic acids under open air
Ando, Shin,Hirota, Yurina,Matsunaga, Hirofumi,Ishizuka, Tadao
, p. 1277 - 1280 (2019)
In this study, a well-defined, novel NHC-Ni complex was developed and used to catalyze the N-arylation of alkyl- and arylamines with arylboronic acids in a rare version of Chan-Lam coupling. Although the same coupling using copper catalysts has been widely studied, the nickel-catalyzed version is rare and normally requires 10–20 mol% catalyst loading. This novel NHC-Ni complex in combination with 4,4′-dimethyl-2,2′-bipyridine, however, proved to be an effective catalyst that lowered the required catalyst loading to only 2.0 mol%.
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.
