Photochromic behavior of several new synthesized bis‐1,3‐diazabicyclo[3.1.0]hex‐3‐enes

Abstract

Photochromic compounds (1-6) are synthesized and characterized and the results of their spectra are presented. The structure-photochromic behavior relationship (SPBR) of the synthesized compounds has been analyzed. H. KIYANI ET AL. 560 Scheme 1. Scheme 2. Synthetic route for the preparation of bis compounds 1-6 Scheme 3. Synthetic route for the preparation of aziridines Scheme 4. Photochromic reactions of 1,3-diazabicyclo [3,1,0]hex-3-ene with phenylene or arylen linkage H NMR (500 MHz, CDCl 3 , ppm):d 2.09-2.12 (m, 4H), 2.53 (s, 2H), 3.54 (s, 2H), 4.03-4.16 (m, 4H), 6.83-6.89 (m, 4H), 6.93 (s, 2H), 7.02 (d, J ¼ 8.8 Hz, 2H), 7.16-7.21 (m, 4H), 7.25 (d, J ¼ 8.6 Hz, 4H), 7.37-7.43 (m, 8H), 7.93 (d, J ¼ 8.5 Hz, 4H), 8.03 (d, J ¼ 8.4 Hz, 4H); after irradiation with UV light converted to blue (open-form, 40%): 1 H NMR (500 MHz, CDCl 3 , ppm): d 1.96-2.03 (m, 4H), 2.55 (s, 2H), 3.56 (s, 2H), 4.03-4.16 (m, 4H), 6.3 (s, 2H), 6.83-6.89 (m, 4H), 7.00 (d, J ¼ 7.5 Hz, 2H), 7.16-7.21 (m, 4H), 7.25 (d, J ¼ 8.6 Hz, 4H), 7.37-7.43 (m, 8H), 7.93 (d, J ¼ 8.5 Hz, 4H), 7.98 (d, J ¼ 8.5 Hz, 4H). Anal. Calcd for C 48 H

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

“…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].…”

“…Both photoisomers are stable and able to give photochromic reactions in the crystalline state. The desired compound 4a was prepared in good yield from the corresponding ketoaziridine compound 1 [5,6] and the available 4-diethoxymethylbenzaldehyde 2, in the presence of ammonium acetate in one-pot reaction (scheme 1). …”

“…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.…”

“…These photochroms and other photochromic compounds such as diarylethenes are promising candidates for application in optical devices [4,5]. Photochromic reactions of bicyclic aziridine compounds include cycloreversion and photocyclization reaction between two forms (i.e., closed-ring and open-ring forms) [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22]. The closed-ring and open-ring isomers of bicyclic aziridines exhibited absorption spectra in solution state.…”

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.…”