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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
Development of a Two-Photon-Responsive Chromophore, 2-(p-Aminophenyl)-5,6-dimethoxy-1-(hydroxyinden-3-yl)methyl
Tuan Phong Nguyen1, Hai Dang Nguyen1, Manabu Abe1,2
1Department of Chemistry, Graduate School of Advance Science and Engineering, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan.
Abstract:
Photoremovable protecting groups (PPGs) are powerful tools that are widely used to investigate biological events in cells. An important requirement for PPGs is the efficient release of bioactive molecules by using visible to near-infrared light in the biological window (650-1350 nm). In this study, we report a new two-photon (2P)-responsive PPG, 2-(p-aminophenyl)-5,6-dimethoxy-1-(hydroxyinden-3-yl)methyl, with a donor-π-donor cyclic stilbene structure. The 2P cross section was approximately 40-50 GM at ∼700 nm. The quantum yield of the uncaging process of caged benzoate was greater than 0.7, demonstrating that the 2P uncaging efficiency was approximately 30 GM at around 700 nm. This newly developed 2P-responsive chromophore can be used in future biological experiments. The mechanism of the photo-uncaging reaction via the carbocation intermediate was elucidated using transient absorption spectroscopy and product analysis.
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