Preparation of Viscosity-Sensitive Isoxazoline/Isoxazolyl-Based Molecular Rotors and Directly Linked BODIPY-Fulleroisoxazoline from the Stable meso-(Nitrile Oxide)-Substituted BODIPY

被引：38
作者：
Zatsikha, Yuriy V. [1 ]
Didukh, Natalia O. [1 ,2 ]
Swedin, Rachel K. [3 ]
Yakubovskyi, Viktor P. [2 ]
Blesener, Tanner S. [1 ]
Healy, Andrew T. [3 ]
Herbert, David E. [1 ]
Blank, David A. [3 ]
Nemykin, Victor N. [1 ]
Kovtun, Yuriy P. [2 ]
机构：
[1] Univ Manitoba, Dept Chem, Winnipeg, MB R3T 2N2, Canada
[2] Natl Acad Sci Ukraine, Inst Organ Chem, 5 Murmanska Str, UA-02660 Kiev, Ukraine
[3] Univ Minnesota, Dept Chem, 207 Pleasant St SE, Minneapolis, MN 55455 USA
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 14期
基金：
加拿大自然科学与工程研究理事会;
关键词：
NITRILE N-OXIDES; PHOTOPHYSICAL PROPERTIES; CYCLOADDITION; DYES; DERIVATIVES; ISOXAZOLES; CHEMISTRY; DIPYRROMETHENES; REDOX;
D O I：
10.1021/acs.orglett.9b02082
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We developed a simple methodology for the preparation of stable meso-(nitrile oxide)-substituted BODIPYs, which were characterized by spectroscopic methods and X-ray crystallography. These compounds were used for the preparation of isoxazoline- or isoxazolyl-BODIPYs by 1,3-dipolar cycloaddition reaction with dipolarophiles. Several BODIPYs possess molecular rotor behavior, including viscosity-dependent fluorescence. Transient absorption spectroscopy and time-resolved fluorescence are indicative of a 3 orders of magnitude difference in the excited-state lifetime for dichloromethane and glycerol solutions.
引用
收藏
页码：5713 / 5718
页数：6
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  • [1] Fluorescent molecular rotors under pressure: synergistic effects of an inert polymer
    Alamiry, Mohammed A. H.
    Bahaidarah, Effat
    Harriman, Anthony
    Bura, Thomas
    Ziessel, Raymond
    [J]. RSC ADVANCES, 2012, 2 (26) : 9851 - 9859
  • [2] Macromolecular Surface Design: Photopatterning of Functional Stable Nitrile Oxides
    Altintas, Ozcan
    Glassner, Mathias
    Rodriguez-Emmenegger, Cesar
    Welle, Alexander
    Trouillet, Vanessa
    Barner-Kowollik, Christopher
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (19) : 5777 - 5783
  • [3] Fluorescent molecular rotors based on the BODIPY motif: effect of remote substituents
    Bahaidarah, Effat
    Harriman, Anthony
    Stachelek, Patrycja
    Rihn, Sandra
    Heyer, Elodie
    Ziessel, Raymond
    [J]. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2014, 13 (10) : 1397 - 1401
  • [4] Molecular Rotors Based on the Boron Dipyrromethene Fluorophore
    Benniston, Andrew C.
    Harriman, Anthony
    Whittle, Victoria. L.
    Zelzer, Mischa
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (03) : 523 - 530
  • [5] Postfunctionalization of the BODIPY Core: Synthesis and Spectroscopy
    Boens, Noel
    Verbelen, Bram
    Dehaen, Wim
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (30) : 6577 - 6595
  • [6] Novel BODIPY-C60 derivatives with tuned photophysical and electron-acceptor properties: Isoxazolino[60]fullerene and pyrrolidino[60]fullerene
    Cabrera-Espinoza, Andrea
    Insuasty, Braulio
    Ortiz, Alejandro
    [J]. JOURNAL OF LUMINESCENCE, 2018, 194 : 729 - 738
  • [7] Synthesis, the electronic properties and efficient photoinduced electron transfer of new pyrrolidine[60]fullerene- and isoxazoline[60]-fullerene-BODIPY dyads: nitrile oxide cycloaddition under mild conditions using PIFA
    Cabrera-Espinoza, Andrea
    Insuasty, Braulio
    Ortiz, Alejandro
    [J]. NEW JOURNAL OF CHEMISTRY, 2017, 41 (17) : 9061 - 9069
  • [8] Imaging phase separation in model lipid membranes through the use of BODIPY based molecular rotors
    Dent, Michael R.
    Lopez-Duarte, Ismael
    Dickson, Callum J.
    Geoghegan, Niall D.
    Cooper, Jonathan M.
    Gould, Ian R.
    Krams, Rob
    Bull, James A.
    Brooks, Nicholas J.
    Kuimova, Marina K.
    [J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2015, 17 (28) : 18393 - 18402
  • [9] Intramolecular geometry and intermolecular interactions of the CNO group of crystalline benzonitrile oxides: a comparison with phenyl cyanates, phenyl isocyanates, and phenyl azides
    Dhami, Jaya K.
    Idzorek, Kiersten M.
    Johnson, Ryan B.
    Van Auken, Kaitlyn S.
    Ojala, William H.
    [J]. CRYSTENGCOMM, 2019, 21 (05): : 908 - 916
  • [10] Flexible BODIPY Platform That Offers an Unexpected Regioselective Heterocyclization Reaction toward Preparation of 2-Pyridone[a]-Fused BODIPYs
    Didukh, Natalia O.
    Yakuboyskyi, Viktor P.
    Zatsikha, Yuriy, V
    Rohde, Gregory T.
    Nemykin, Victor N.
    Kovtun, Yuriy P.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (04) : 2133 - 2147
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