Photochromic Properties of Novel One‐pot Multicomponent Synthesized Tetraarylimidazoles

Abstract

Acetic acid mediated synthesis of novel tetraarylimidazoles derivatives has been reported via multicomponent reaction of benzil or phenanthrene‐9,10‐dione, NH4OAc, vanillin and aniline derivatives under microwave irradiation. Several novel tetraarylimidazole derivatives, phenanthroimidazole and bis‐tetraphenylimidazole bearing a 2‐methoxyphenol substituent at position 2 of imidazole ring were prepared. The advantages of this method are the one‐pot preparation of compounds, in short reaction times (4‐7 min) and good yields. All synthesized compounds with a 2‐methoxyphenol substituent at position 2 of imidazole ring exhibited good photochromic behavior. The photoisomerization can be performed from ground state to triplet excited state according to TD‐DFT calculation. The results showed that the presence of ortho‐methoxy substituent to hydroxyl substitution has the greatest effect on photochromic properties of target compounds. Furthermore, a pattern was successfully visualized upon UV light irradiation, which suggested that these compounds can be served as a security ink or an anti‐counterfeiting mark for photo printing.

Design, synthesis, and biological evaluation of 1,4,7,8‐tetrahydro‐5H‐furo[3,4‐b]pyrazolo[4,3‐e]pyridin‐5‐one‐based azo dyes

“…Changes on the scaffold of 1,4‐DHP analogs, considering their important biological properties, may also cause significant changes in their biological activities, which may contain interesting properties. Therefore, following our previous work [33–38], here we report a 3MCR consisting of an AZA, TA, and 5‐aminopyrazole (5‐AP) under microwave irradiation for the first time (Figure 1). Then, all synthesized compounds were evaluated regarding AO and antibacterial activity.…”

Alkaline Transition Metal‐Free Oxidative Coupling of Benzylic and Quasi Benzylic sp3 Bonds with O2

“…[11] In our case, we used reactants containing benzylic and quasi-benzylic bonds of primary and secondary alkyl aryls, such as toluene, pyridine, and quinoline derivatives, to undergo an OC with molecular oxygen and MeOH-KOH solution without a transition metal catalyst. In contribution to our previous interest , [12][13][14][15][16][17][18][19][20][21] in this paper we use the H-benzylic oxidation strategy to obtain an in situ green transition-metal-free OC for Csp 3 À Csp 3 bond formation.…”

One‐pot Multicomponent Synthesis of Novel Chromene Derivatives Using New Organic Phosphate Salt Catalysts

“…Thus, from the viewpoint of synthetic chemists, these reactions contribute significantly to synthesizing heterocyclic compounds in organic chemistry. [1][2][3][4][5][6][7][8][9][10][11] Chromenes and pyrans are considerably important heterocyclic compounds attracting the attention of scientists due to their various significant biological effects, including anticancer, [12][13][14] antibacterial, [15,16] antioxidant, [17] antimycobacterial [18,19] and anti-epileptic [20] (Figure 1).…”