Photo-Fries rearrangement of phenyl salicylate studied by two-dimensional infrared spectroscopy

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• 作者：Hideyuki Shinzawa ; ^{h-shinzawa@aist.go.jp" class="auth_mail" title="E-mail the corresponding author} ; Yuki Matsumoto ; Seiji Tsuzuki ; Yukihiro Shimoi ; Hiroyuki Suda
• 关键词：Photo-Fries rearrangement ; Phenyl salicylate ; Infrared (IR) spectroscopy ; Two-dimensional (2D) correlation spectroscopy ; Density functional theory (DFT)
• 刊名：Vibrational Spectroscopy
• 出版年：2015
• 出版时间：November 2015
• 年：2015
• 卷：81
• 期：Complete
• 页码：131-135
• 全文大小：1097 K

文摘

Photo-Fries rearrangement of phenyl salicylate was examined by real-time infrared (IR) monitoring in conjunction with density functional theory (DFT) calculation. Changes in the spectral features were readily captured during the photo-induced chemical reaction of the phenyl salicylate by means of two-dimensional (2D) correlation spectroscopy. The obvious variations of spectral intensities due to the production of 2,2′-dihydroxybenzophenone and 2,4′-dihydroxybenzophenone are clearly identified to provide in-depth understanding to the photo-Fries rearrangement. Namely, when exposed to UV-irradiation, the majority of the phenyl salicylate undergoes photothermal degradation. Further irradiation to the rest of the phenyl salicylate then results in the production of 2,2′-dihydroxybenzophenone followed by the development 2,4′-dihydroxybenzo-phenome products. Such delay in the production of 2,4′-dihydroxybenzo-phenome implies the presence of some more pathways, which makes its reaction efficiency lower than that of 2,2′-dihydroxybenzophenone.