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  1. NázovArylazoindazole photoswitches
    Podnázovfacile synthesis and functionalization via SNAr substitution
    Aut.údajeRaquel Travieso-Puente ... [et al.]
    Autor Travieso-Puente Raquel (15%)
    Spoluautori 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%)
    Zdroj.dok. Journal of the American Chemical Society. Vol. 139, no. 9 (2017), pp. 3328-3331. - Washington : The American Chemical Society, 2017
    Kľúč.slová arylazoindazoles   arylindazoly   fotoprepínače - photoswitches  
    Jazyk dok.angličtina
    KrajinaSpojené štáty
    Systematika 66.0
    AnotáciaA 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.
    Kategória publikačnej činnosti ADC
    Číslo archívnej kópie41291
    Kategória ohlasu 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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    MU, Ge - WEN, Zhili - WU, Judy I-Chia - TEETS, Thomas S. Azo-triazolide bis-cyclometalated Ir(III) complexes via cyclization of 3-cyanodiarylformazanate ligands. In Dalton transactions. ISSN 1477-9226, 2020, vol. 49, no. 12, pp. 3775-3785.
    KENNEDY, Aaron D. W. - SANDLER, Isolde - ANDREASSON, Joakim - HO, Junming - BEVES, Jonathon E. Visible-light photoswitching by azobenzazoles. In Chemistry : a European journal. ISSN 0947-6539, 2020, vol. 26, no. 5, pp. 1103-1110.
    HUANG, He - LAMBERT, Tristan H. Electrophotocatalytic SNAr reactions of unactivated aryl fluorides at ambient temperature and without base. In Angewandte Chemie : international edition. ISSN 1433-7851, 2020, vol. 59, no. 2, pp. 658-662.
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    ZHANG, Zhao-Yang - HE, Yixin - ZHOU, Ying - YU, Chunyang - HAN, Lu - LI, Tao. Pyrazolylazophenyl ether-based photoswitches : facile synthesis, (near-)quantitative photoconversion, long thermal half-life, easy functionalization, and versatile applications in light-responsive systems. In Chemistry : a European journal. ISSN 0947-6539, 2019, vol. 25, no. 58, pp. 13402-13410.
    MAO, Jianyou - WANG, Zhiting - XU, Xinyu - LIU, Guoqing - JIANG, Runsheng - GUAN, Haixing - ZHENG, Zhipeng - WALSH, Patrick J. Synthesis of indoles through domino reactions of 2-fluorotoluenes and nitriles. In Angewandte Chemie : international edition. ISSN 1433-7851, 2019, vol. 58, no. 32, pp. 11033-11038.
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    CRESPI, Stefano - SIMETH, Nadja A. - BELLISARIO, Alfredo - FAGNONI, Maurizio - KOENIG, Burkhard. Unraveling the thermal isomerization mechanisms of heteroaryl azoswitches : phenylazoindoles as case study. In Journal of physical chemistry A. ISSN 1089-5639, 2019, vol. 123, no. 9, pp. 1814-1823.
    CRESPI, Stefano - SIMETH, Nadja A. - KOEINIG, Burkhard. Heteroaryl azo dyes as molecular photoswitches. In Nature reviews chemistry. ISSN 2397-3358, 2019, vol. 3, no. 3, pp. 133-146.
    HONEYCUTT, Aaron P. - HOOVER, Jessica M. Nickel-catalyzed oxidative decarboxylative annulation for the synthesis of heterocycle-containing phenanthridinones. In Organic letters. ISSN 1523-7060, 2018, vol. 20, no. 22, pp. 7216-7219.
    PURKAYASTHA, Atanu - FRONTERA, Antonio - GANGULY, Rakesh - MISRA, Tarun K. Synthesis, structures, and investigation of noncovalent interactions of 1,3-dimethyl-5-(4 '/3 '-pyridylazo)-6-aminouracil and their Ni(II) complexes. In Journal of molecular structure. ISSN 0022-2860, 2018, vol. 1170, pp. 70-81.
    JANARDHANAN, Jith C. - MISHRA, Rakesh K. - DAS, Gourab - SINI, Suresh - JAYAMURTHY, Purushothaman - SURESH, Cherumuttathu H. - PRAVEEN, Vakayil K. - MANOJ, Narayanapillai - BABU, Beneesh P. Functionalizable 1H-indazoles by palladium catalyzed aza-nenitzescu reaction : pharmacophores to donor-acceptor type multi-luminescent fluorophores. In Asian journal of organic chemistry. ISSN 2193-5807, 2018, vol. 7, no. 10, pp. 2094-2104.
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    ZHOU, Quan - HONG, Xi - CUI, He-Zhen - HUANG, Shuang - YI, Ying - HOU, Xiu-Feng. The construction of C-N, C-O, and C(sp(2))-C(sp(3)) bonds from fluorine-substituted 2-aryl benzazoles for direct synthesis of N-, O-, C-functionalized 2-aryl benzazole derivatives. In Journal of organic chemistry. ISSN 0022-3263, 2018, vol. 83, no. 12, pp. 6363-6372.
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