Click chemistry refers to selective reactions developed for grafting of bio(macro)molecules in their biological media. Caged click compounds have been employed to spatiotemporally control click reactions. Here, we survey the uncaging of photo-dibenzocyclooctyne-OH (photoDIBO-OH) to its click-chemistry active form DIBO-OH, with particular attention to its conversion timescale and efficiency. Ultraviolet pump–infrared probe experiments reveal a stepwise decarbonylation: first, carbon monoxide (C≡O) is released within 1.8 ps, and then, it converts, within 10 ps, to DIBO-OH. Completion of uncaging is achieved with an efficiency of ∼50%. A successful demonstration of two-photon uncaging of photoDIBO-OH at long wavelength (700 nm) confers enhanced in vivo compatibility and proceeds on the same timescale.

中文翻译：

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切换点击：时间分辨红外光谱跟踪 photoDIBO-OH 的超快光化学

点击化学是指为在生物介质中接枝生物（大）分子而开发的选择性反应。笼状点击化合物已被用来时空控制点击反应。在这里，我们研究了光二苯并环辛炔-OH (photoDIBO-OH) 对其点击化学活性形式 DIBO-OH 的解束缚，特别关注其转换时间尺度和效率。紫外泵-红外探针实验揭示了逐步脱羰作用：首先，一氧化碳 (C^O) 在 1.8 ps 内释放，然后在 10 ps 内转化为 DIBO-OH。完成解锁的效率约为 50%。成功演示了 photoDIBO-OH 在长波长（700 nm）下的双光子解禁，增强了体内兼容性，并在相同的时间尺度上进行。