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https://doi.org/10.1016/j.jphotochem.2024.116194
Copy DOIPublication Date: Dec 1, 2024 |
A series of 5-(dimethoxyphenyl)-1,3-diphenylpyrazoles containing two methoxy groups on the different C5-aryl ring positions were synthesized and the electronic and steric effects, especially the position of the methoxy substitutions on the outcome of their photoreaction were investigated. Furthermore, the effect of the type and nature of solvent (chloroform or cyclohexane) in the progress of the photoreaction are also investigated. The photochemical results indicated the formation of two different phenanthridine products depending on the used solvent. Based on the proposed photo-induced electron-transfer mechanism in CHCl3 solution, the methoxy group on the ortho-position is eliminated during the photo-cyclization process and a chlorine atom is added to one of the allowed C5-aryl ring positions. While the observed photo-cyclization reaction in cyclohexane solvent occurs via complexation mechanism, which strongly requires the presence of the methoxy group on the ortho-position. In this case, complexation of the ortho-methoxy group to the N1-phenyl ring started the cyclization process, resulting in the formation of the phenanthridine photoproducts by elimination of this group. The phenanthridine products of both photoreactions are characterized by the analysis of their FT-IR, 1H NMR, 13C NMR, UV–Vis and Mass spectra. In addition, DFT computational studies were carried out to support the results of the experimental study.
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