Cooperative Veratryle and Nitroindoline Cages for Two-Photon Uncaging in the NIR

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• 作者：Dr. Eduardo Cueto Diaz ; Dr. Sé ; bastien Picard ; Maxime Klausen ; Vincent Hugues ; Paolo Pagano ; Dr. Emilie Genin and Dr. Mireille Blanchard-Desce
• 刊名：Chemistry - A European Journal
• 出版年：2016
• 出版时间：July 25, 2016
• 年：2016
• 卷：22
• 期：31
• 页码：10848-10859
• 全文大小：1426K
• ISSN：1521-3765

文摘

Tandem uncaging systems in which a two-photon absorbing module and a cage moiety, linked via a phosphorous clip, that act together by Förster resonance energy transfer (FRET) have been developed. A library of these compounds, using different linkers and cages (7-nitroindolinyl or nitroveratryl) has been synthesized. The investigation of their uncaging and two-photon absorption properties demonstrates the scope and versatility of the engineering strategy towards efficient two-photon cages and reveals surprising cooperative and topological effects. The interactions between the 2PA module and the caging moiety are found to promote cooperative effects on the 2PA response while additional processes that enhance the uncaging efficiency are operative in well-oriented nitroindoline-derived dyads. These synergic effects combine to lead to record two-photon uncaging cross-section values (i.e., up to 20 GM) for uncaging of carboxylic acids.