Synthesis of anthracene derivatives of 1,3-diazabicyclo[3.1.0]hex-3-ene

• Synthesis of mono- and bis-1,3-diazabicyclo[3.1.0]hex-3-enes with anthracene moiety.
• Photochromic behavior of both mono- and bis-compounds.
• Photochromic behavior in solution and in solid state.
• Irradiation under UV light at 254 nm.

Novel mono- and bis-photochromic compounds of 1,3-diazabicyclo[3.1.0]hex-3-enes based on anthracene moiety were synthesized efficiently. Photochromic compounds were synthesized through the reaction of 10-(hydroxymethyl)anthracene-9-carbaldehyde and anthracene-9-carbaldehyde or 9,10-anthracenedicarbaldehyde as bis-aldehydes with ketoaziridines in dry DMF at room temperature. Photochromic compounds exhibited photochromic behavior both in solution and in solid state by irradiation under UV light at 254 nm. Compounds bearing 4-NO2 on aziridine moiety showed intensive color change. Compounds were characterized by IR, 1H NMR, 13C NMR, and UV–Vis.

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