Redox Control over Acyl Hydrazone Photoswitches

Ivica Cvrtila, Hugo Fanlo-Virgos, Gael Schaeffer, Guillermo Monreal Santiago, Sijbren Otto*

*Bijbehorende auteur voor dit werk

OnderzoeksoutputAcademicpeer review

38 Citaten (Scopus)
321 Downloads (Pure)

Samenvatting

Photoisomerization provides a clean and efficient way of reversibly altering physical properties of chemical systems and injecting energy into them. These effects have been applied in development of systems such as photoresponsive materials, molecular motors, and photoactivated drugs. Typically, switching from more to less stable isomer(s) is performed by irradiation with UV or visible light, while the reverse process proceeds thermally or by irradiation using another wavelength. In this work we developed a method of rapid and tunable Z -> E isomerization of C = N bond in acyl hydrazones, using aromatic thiols as nucleophilic catalysts. As thiols can be oxidized into catalytically inactive disulfides, the isomerization rates can be controlled via the oxidation state of the catalyst, which, together with the UV irradiation, provides orthogonal means to control the E/Z state of the system. As a proof of this concept, we have applied this method to control the diversity of acyl hydrazone based dynamic combinatorial libraries.

Originele taal-2English
Pagina's (van-tot)12459-12465
Aantal pagina's7
TijdschriftJournal of the American Chemical Society
Volume139
Nummer van het tijdschrift36
DOI's
StatusPublished - 13-sep-2017

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