6337-15-1Relevant articles and documents
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
supporting information, p. 5277 - 5287 (2016/04/09)
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.
Synthesis and biological activity of some heterocyclic systems containing anthraquinone
Berghot,Hanna,Girges
, p. 340 - 343 (2007/10/02)
2-Aminoanthraquinone (1) was reacted with ethyl chloroformate to afford 2. The reaction between carbamate 2 and hydrazine hydrate gave semicarbazide 3, which on treatment with benzoic acid, phenyl isothiocyanate and carbondisulfide/potassium hydroxide furnished oxadiazoles 4, 6 and triazole 5, respectively. Also, treatment of 1 with chloroacetyl chloride gave chloroacetyl derivative 8. The reaction of glycolic acid, thioglycolic acid, diethylmalonate and malononitrile with 8 has been investigated. Compound 8 was treated with potassium thiocyanate to give 12, which was cyclized to 13a, while the reaction between 8 and potassium cyanate gave 13b directly. The structures of hitherto unknown compounds were confirmed by analytical and spectral methods. Some of the synthesized compounds were screened to test their antibacterial and antifungal properties.