125309-56-0Relevant academic research and scientific papers
Exploration of the Photodegradation of Naphtho[2,3-g] quinoxalines and Pyrazino[2,3-b]phenazines
Kolmer-Anderl, Nicole,Kolmer, Andreas,Thiele, Christina M.,Rehahn, Matthias
, p. 5277 - 5287 (2016)
Nitrogen-containing polycyclic aromatic hydrocarbons are very attractive compounds for organic electronics applications. Their low-lying LUMO energies points towards a potential use as n-type semiconductors. Furthermore, they are expected to be more stable under ambient conditions, which is very important for the formation of semiconducting films, where materials with high purity are needed. In this study, the syntheses of naphtho[2,3-g]quinoxalines and pyrazino[2,3-b]phenazines is presented by using reaction conditions, that provide the desired products in high yields, high purity and without time-consuming purification steps. The HOMO and LUMO energies of the compounds are investigated by cyclic voltammetry and UV/Vis spectroscopy and their dependency on the nitrogen content and the terminal substituents are examined. The photostability and the degradation pathways of the naphtho[2,3-g]quinoxalines and pyrazino[2,3-b]phenazines are explored by NMR spectroscopy of irradiated samples affirming the large influence of the nitrogen atoms in the acene core on the degradation process during the irradiation. Finally, by identifying the degradations products of 2,3-dimethylnaphtho[2,3-g]quinoxaline it is possible to track down the most reactive position in the compound and, by blocking this position with nitrogen, to strongly increase the photostability.
On the synthesis of pyrazino[2,3-b]phenazine and 1H-imidazo[4,5-b]phenazine derivatives
Amer, Atef M.,El-Bahnasawi, Adel A.,Mahran, Mohamed R.H.,Lapib, Mostafa
, p. 1217 - 1225 (2007/10/03)
Several pyrazino[2,3-b]pnenazine derivatives were prepared by the reaction of 2,3-diaminophenazine with different 1,2-diketones. Nucleophilic substitution of 2,3-dibromomethylpyrazino[2,3-b]phenazine with propanol, morpholine, and potassium thiocyanate gave 2,3-bis-(propoxymethyl )-pyrazino[2,3-b]phenazine, 2,3-bis-(4-morpholinylmethyl)-pyrazino[2,3-b]phenazine, and 2,3-bis-(cyanosulfanylmethyl)-pyrazino[2,3-b]phenazine, 2-Aryl-1H-imidazo[4,5-b]phenazine derivatives were synthesized by a one-pot reaction of 2,3-diaminophenazine with different aromatic aldehydes or acids. Reaction of 2,3-diaminophenazine with acetic anhydride and formic acid afforded 1H-imidazo [4,5-b]phenazine and 2-methyl-1H-imidazo[4,5-b]phenazine. Chemical and spectroscopic evidences for the product structures of the new compounds arc presented.
Structural Requirement for the J-Aggregate Formation in Dicycloheptapyrazinoquinoxaline-3,11-diones and Related Compounds
Takeshita, Hitoshi,Mori, Akira,Nagao, Tomohiro,Nagamura, Toshihiko
, p. 1719 - 1722 (2007/10/02)
Two tetrapropyl derivatives of dicycloheptapyrazinoquinoxaline-3,11-dione and 9,11-dipropylcycloheptapyrazinophenazin-10-one, revealed the J-band in conc H2SO4.On the other hand, 2,3-diphenylcycloheptapyrazinoquinoxalin
