Photochemistry of unsaturated nitrogen-containing compounds. VIII. Photochemistry of benzophenone azine

Abstract

Benzophenone azine (1) has been found to be the beginning point for two different types of photochemical reaction. The first of these is a molecular rearrangement leading to 1,3,3-triphenylisoindole (5) while the second is a photoreduction resulting in the formation of 1,1,1',!'-tetraphenylazomethane (7). l,l,l',l'-Tetraphenylazomethane (7) has also been found to be photochemically unstable yielding 1,1,2,2-tetraphenylethane (2) and diphenylmethane (3). 1,1,2,2-Tetraphenylethane (2) has been previously shown to decompose upon photolysis to give cfs-stilbene (4), l-(2-biphenylyl)-l,2-diphenylethane (6), and biphenyl (8). All of these compounds (2-8) are isolated from the photolysis of benzophenone azine (1).Benzophenone azine (1) has been found to be photochemically unique among azine systems. It does not participate in nitrogen-nitrogen bond homolysis, the major light-initiated reaction experienced by other acyclic azines.3 It does, however, undergo two reac-^)C=NN=C^^) C=N• -N=Ct ions, a photoreduction and a molecular rearrangement.At this time we would like to describe our findings related to these two photochemical reactions of benzophenone azine (1). ResultsVycor-filtered irradiation of 3.00 mmol of benzophenone azine (1) in 1200 ml of methanol under nitrogen for 24 hr with a 450-W Hanovia mercury-vapor lamp produced, after solvent removal, a dark yellow oil containing some solid material. Chromatography (1) Paper VIII in a series on the photochemistry of unsaturated nitrogencontaining compounds. For paper VII see R. W.

Unraveling the Potential Role of Deep Eutectic Solvents (DESs): Synthesis of Ketazines & Pyrazolines

“…In recent years, azines have received a considerable interest of the scientific community because of their noteworthy physiochemical properties for example, electron delocalization, unique reactivity pattern, charge distribution, E/Z ‐isomerization, conformational isomerism tautomerism, and polymorphisim addition to their materialistic signatures [2–5] . Moreover, azines are considered as the constructive frameworks for the synthesis of various valued N ‐heterocycles such as pyrazoles, diazepines, triazoles, isoquinolines, pyrroles, dihydropyridines, imidazopyridines, triazines, and oxadiazoles etc [6–16] . Besides these, azines are also measured as the promising candiates for the design and construction of the molecular organic frameworks (MOFs), covalent organic frameworks (COFs), liquid crystals, nonlinear optical (NLO), electro‐ or photo‐switchable devices and conducting, sensing & energetic materials etc [17–23] .…”

“…[2][3][4][5] Moreover, azines are considered as the constructive frameworks for the synthesis of various valued N-heterocycles such as pyrazoles, diazepines, triazoles, isoquinolines, pyrroles, dihydropyridines, imidazopyridines, triazines, and oxadiazoles etc. [6][7][8][9][10][11][12][13][14][15][16] Besides these, azines are also measured as the promising candiates for the design and construction of the molecular organic frameworks (MOFs), covalent organic frameworks (COFs), liquid crystals, nonlinear optical (NLO), electro-or photo-switchable devices and conducting, sensing & energetic materials etc. [17][18][19][20][21][22][23] From the biological aspects, functionalized azine derivatives display important therapeutic applications such as antiparasitic, anti-hypertensive (Guanabenz), antimicrobial, anti-parasitic, anti-cancer and anti-prion activities.…”

Thermochromie und Photochromie arylsubstituierter Azine;1) Benzophenonanthraldazin

“…Anthracen in amlnalkallseher LdsungUntersuchungen des Antraceneinflusses auf die Anthrachinonphotoreduktion wurden bisher nur im Hinblick auf das Laschen photoangeregter Zustande des Anthrachinons (A) durch Anthracen (Ac) durchgefiihrt. Yon mehreren Autoren konnte die Energieiibertragung vom Triplettzustand des photoangeregten Anthrachinons auf Anthracen nachgewiesen werden[1]-[3]. Dabei wurde die Wellenlange des Anregungslichtes immer so gewahlt, daB sie der n, n*-Bande des Anthrachinons (400 nm], nicht aber der n,n*-Bande des Anthracene (360 nm) entsprach.…”