Synthesis and Photochromic Properties of New Heterocyclic Derivatives of 1,3‐Diazabicyclo[3.1.0]Hex‐3‐Ene

Abstract

The facile synthesis of several 1,3‐diazabicyclo[3.1.0]hex‐3‐ene derivatives with varying substitutions such as 2‐methyl‐6‐(4‐nitrophenyl)‐2,4‐diphenyl‐(1), 2‐methyl‐6‐(4‐nitrophenyl)‐4‐phenyl‐2‐(pyridin‐3‐yl)‐(2), 2‐(furan‐2‐yl)‐6‐(4‐nitrophenyl)‐4‐phenyl‐(3), 2‐(furan‐2‐yl)‐6‐(3‐nitrophenyl)‐4‐phenyl‐(4), 6‐(3‐nitrophenyl)‐2,4‐diphenyl‐(5) and 6‐(4‐chlorophenyl)‐4‐(3‐nitrophenyl)‐2‐phenyl‐(6) that all behave as “intelligent materials” are reported.

2-(4-Diethoxymethylphenyl)-6-(4-nitrophenyl)-4-phenyl-1,3-diazabicyclo[3.1.0]hex-3-ene

“…Apart from the color, the two forms also differ in various physical and chemical properties such as refractive indexes, dielectric constants, oxidation-reduction potentials, and molecular geometry [1][2][3][4][5][6]. Bicyclic aziridine derivatives, very fascinating classes of organic photochromic compounds, have special photochromic properties.…”

“…This property lets me to study them as nominees in the search for intelligent photochromic materials. Depending on the particular structure, 1,3-diazabicyclo[3.1.0]hex-3-ene derivative crystals showed different colors upon UV irradiation [5][6][7][8]. These photochroms and other photochromic compounds such as diarylethenes are promising candidates for application in optical devices [4,5].…”

2-(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-6-(4-nitrophen­yl)-4-phenyl-1,3-diazabicyclo[3.1.0]hex-3-ene

“…Then, the Vilsmeier-Haack reaction of the resulted product pyrazolon derivative lead to chloroformylation to obtain required 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (3). The starting ketoaziridine 1 was prepared according previously to the described method [13][14][15][16]. The structure of 7a is supported by spectral data.…”

NMR structural elucidation and photochromic behavior of new 1,3-diazabicyclo[3.1.0]hex-3-ene derivatives

“…The melting points were a In the solid state. [17], 2,3-dibromo-3-(4-nitrophenyl)-1-phenylpropan-1-one (XIV) [11,13], and [3-(4-nitrophenyl)aziridin-2-yl](phenyl)methanone (XV) [10] were prepared according to known methods.…”

“…In the present article we report on several new photochromic compounds that are derivatives of well known photochromic 1,3-diazabicyclo[3.1.0]hex-3-ene system. Compounds I-XII with different substituents in the 2-position were synthesized following a slightly modified known procedure [10][11][12][13][14] (Scheme 1). Benzoylaziridines XV were prepared starting from chalcones XIII which were subjected to bromination at the double bond with bromine in chloroform solution to obtain dibromo derivatives XIV, followed by aziridination with a solution of ammonia in anhydrous ethanol at room temperature [10].…”