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

被引：46

作者：

Chitose, Youhei ^{[1
]}

Abe, Manabu ^{[1
]}

Furukawa, Ko ^{[2
]}

Ling, Jhe-Yi ^{[3
]}

Lin, Tzu-Chau ^{[3
]}

Katan, Claudine ^{[4
]}

机构：

[1] Hiroshima Univ, Grad Sch Sci, Dept Chem, 1-3-1 Kagarniyama, Higashihiroshima, Hiroshima 7398526, Japan

[2] Niigata Univ, Ctr Instrumental Anal, Nishi Ku, 8050 Ikarashi 2 No Cho, Niigata 9502181, Japan

[3] Natl Cent Univ, Dept Chem, Photon Mat Res Lab, Taoyuan 32001, Taiwan

[4] Univ Rennes 1, CNRS, Inst Sci Chim Rennes, UMR 6226, F-35042 Rennes, France

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 10期

关键词：

PHOTORELEASE TECHNOLOGY; PROTECTING GROUPS; GENERATION; CHEMISTRY; ESTERS; PROBES;

D O I：

10.1021/acs.orglett.7b00957

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A caged carboxylic acid with a novel two-photon (TP)-responsive donor-pi-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 (epsilon approximate to 29000 cm(-1) M-1) in the visible region (>similar to 400 nm). Time-dependent density functional theory calculations predicted a sizable TP absorption cross-section with a maximum at similar to 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.

引用

页码：2622 / 2625

页数：4

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