70593-66-7Relevant academic research and scientific papers
Oxidative Cyclizations. VIII. Mechanisms of Oxidation of ortho-Substituted Benzenamines and Improved Cyclizations by Bis(acetato-O)phenyliodine
Dyall, Leonard K.,Harvey, Jacqueline J.,Jarman, Tony B.
, p. 371 - 384 (1992)
Published reports describe the oxidative cyclization of suitable ortho-substituted arenamines to form such products as 2,1-benzisoxazoles, benzofurazan 1-oxides and benzotriazoles, by using bis(acetato-O)phenyliodine at room temperature.However, the reactions are often inconveniently slow.We now report attempts to achieve short reaction times with more powerful iodine(III) oxidants.These often failed to give cyclic products, but the results enable us to argue that the reaction competing with cyclization involves the arenaminyl cation ArN+H.When such cations are predicted to be relatively unstable, the parent arenamine can be rapidly cyclized in high yield by oxidation with bis(acetato-O)phenyliodine in boiling benzene.
Bipyridyl-substituted benzo[1,2,3]triazoles as a thermally stable electron transporting material for organic light-emitting devices
Ichikawa, Musubu,Mochizuki, Shunji,Jeon, Hyeon-Gu,Hayashi, Shuichi,Yokoyama, Norimasa,Taniguchi, Yoshio
experimental part, p. 11791 - 11799 (2011/10/31)
We developed new electron-transporting materials (ETMs) for organic light-emitting devices (OLEDs) based on benzo[1,2,3]triazole and two bipyridines. Four derivatives based on the same skeleton were synthesized with four different substituents: phenyl (BpyBTAZ-Ph), biphenyl (-BP), m-terphenyl (-mTP), and o-terphenyl (-oTP). These BpyBTAZ compounds have good thermal stabilities, and their decomposition temperatures were greater than 410 °C, which is significantly higher than that of tris(8-quinolinolato)aluminium (Alq), the conventional OLED material. BpyBTAZ compounds show preferable amorphous nature, and moreover, the glass transition temperatures (Tgs) of both BpyBTAZ-TP compounds exceed 100 °C. Furthermore, BpyBTAZ-BP exhibits no melting point and is fully amorphous. The electron affinities of the materials are as large as 3.3 eV and their electron mobility is sufficiently high. These characteristics accounted for a reduction in the operational voltage of OLEDs with BpyBTAZ compounds compared with the reference device with Alq as an ETM. Specifically, the electron mobility of all the BpyBTAZ compounds exceeds 1 × 10-4 cm2 V-1 s-1 at an electric field of 1 MV cm-1. In addition, it was revealed that both BpyBTAZ-TP-based devices showed longer luminous lifetimes and smaller voltage increases during continuous operation at 50 mA cm-2, compared with the Alq reference device. The Royal Society of Chemistry 2011.
Pyrolysis of Aryl Azides. V. Characterization of Phenylazo, Benzoyl and Formyl as Neighbouring Groups
Dickson, Noel J.,Dyall, Leonard K.
, p. 91 - 99 (2007/10/02)
The enhancements of thermolysis rate of azidobenzene produced by ortho phenylazo, benzoyl and formyl substituents are 21180, 70.0 and 22.8 at 393.2 K (decalin solutions).The same ortho substituents produce much smaller enhancements (169, 8.56 and 10.7 respectively) in the pyrolysis rate of 1-azido-2,4-dibromobenzene.These results are interpreted as steric effects on an electrocyclic thermolysis mechanism, and are not consistent with the alternative pathway of intramolecular 1,3-dipolar addition which continues to be advocated by Hall and Dolan.
