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Published on: August 19, 2012
Arylazopyrazoles for Conjugation by CuAAC Click Chemistry
Alisa-Maite Kauth1, Rebecca Niebuhr1, Bart Jan Ravoo1
1Center for Soft Nanoscience and Organic Chemistry Institute, University of Münster, Busso-Peus-Straße 10, D-48149 Münster, Germany.
Abstract:
Molecular photoswitches are increasingly being implemented in bioactive compounds and responsive materials. For this purpose, photoswitches must be coupled to a wide variety of substrates and scaffolds. We present a library of "clickable" arylazopyrazoles (AAPs), which can be conjugated by Cu-catalyzed alkyne azide cycloaddition (CuAAC). All synthesized AAP alkynes show good photostationary states (at least 88%) and long half-life times of the Z-isomer (18 to 108 h). The AAP azides decompose upon exposure to ultraviolet (UV) irradiation, but after CuAAC, all AAPs exhibit good photophysical properties.
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