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Arylazoindazole photoswitches
Title Arylazoindazole photoswitches Subtitle facile synthesis and functionalization via SNAr substitution Author info Raquel Travieso-Puente ... [et al.] Author Travieso-Puente Raquel (15%)
Co-authors Budzák Šimon 1982- (14%) UMBFP08 - Katedra chémie
Chen Juan (14%)
Stacko Peter (14%)
Jastrzebski Johann T. B. H. (14%)
Jacquemin Denis (14%)
Otten Edwin (15%)
Source document Journal of the American Chemical Society. Vol. 139, no. 9 (2017), pp. 3328-3331. - Washington : The American Chemical Society, 2017 Keywords arylazoindazoles arylindazoly fotoprepínače - photoswitches Language English Country United States of America systematics 66.0 Annotation A straightforward synthetic route to arylazoindazoles via nucleophilic aromatic substitution is presented. Upon deprotonation of the NH group, a C(6)F(5-)substituted formazan undergoes facile cydization as a result of intermolecular nucleophilic substitution (SNAr). This new class of azo photoswitches containing an indazole five-membered heterocycle shows photochemical isomerization with high fatigue resistance. In addition, the Z-isomers have long thermal half-lives in the dark of up to several days at room temperature. The fluorinated indazole group offers a handle for further functionalization and tuning of its properties, as it is shown to be susceptible to a subsequent, highly selective nucleophilic displacement reaction. Public work category ADC No. of Archival Copy 41291 Repercussion category VELA, Sergi - SCHEIDEGGER, Alan - FABREGAT, Raimon - CORMINBOEUF, Clemence. Tuning the thermal stability and photoisomerization of azoheteroarenes through macrocycle strain. In Chemistry : a European journal. ISSN 0947-6539, 2021, vol. 27, no. 1, pp. 419-426.
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