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Design and Synthesis of a Caged Carboxylic Acid with a Donor-π-Donor Coumarin Structure: One-photon and Two- photon Uncaging Reactions Using Visible and Near-Infrared Lights

Abstract : A caged carboxylic acid with a novel two-photon (TP)-responsive donor-π-donor coumarin backbone with a quadrupolar nature was designed and synthesized in this study. The newly synthesized coumarin derivative showed a strong one-photon (OP) absorption band (ε ≈ 29000 cm M) in the visible region (>∼400 nm). Time-dependent density functional theory calculations predicted a sizable TP absorption cross-section with a maximum at ∼650 nm significantly lager than that related to the OP absorption band. This is confirmed experimentally using TP excited fluorescence in the fs regime that leads to TP absorption cross-section of 18 and 5.6 GM at 680 and 760 nm, respectively. The OP photolysis (400 nm) and near-infrared-TP photolysis (750 nm) of the caged benzoic acid resulted in a clean formation of benzoic acid and an aldehyde.
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Submitted on : Tuesday, May 30, 2017 - 5:41:45 PM
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Youhei Chitose, Manabu Abe, Ko Furukawa, Jhe-Yi Lin, Tzu-Chau Lin, et al.. Design and Synthesis of a Caged Carboxylic Acid with a Donor-π-Donor Coumarin Structure: One-photon and Two- photon Uncaging Reactions Using Visible and Near-Infrared Lights. Organic Letters, American Chemical Society, 2017, 19 (10), pp.2622-2625. ⟨10.1021/acs.orglett.7b00957⟩. ⟨hal-01527343⟩

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