Design and synthesis of laser-activatable tetrazoles for a fast and fluorogenic red-emitting 1,3-dipolar cycloaddition reaction.

Design and synthesis of laser-activatable tetrazoles for a fast and fluorogenic red-emitting 1,3-dipolar cycloaddition reaction.
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DOI:
10.1021/ol402645q
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发表时间:
2013-11-01
期刊:
影响因子:
5.2
通讯作者:
Lin, Qing
Lin, Qing
中科院分区:
化学1区
文献类型:
--
作者:
An, Peng;Yu, Zhipeng;Lin, Qing

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The design and synthesis of a new class of laser light activatable tetrazoles with extended π systems is reported. Upon 405 nm laser light irradiation, these bithiophene-substituted tetrazoles underwent extremely fast 1,3-dipolar cycloaddition reactions with dimethyl fumarate with second-order rate constants approaching 4000 M−1 s−1. The resulting pyrazoline cycloadducts exhibited solvent-dependent red fluorescence, making these tetrazoles potentially useful as fluorogenic probes for detecting alkenes in vivo.
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