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

Yuriy V. Zatsikha, Natalia O. Didukh, Rachel K. Swedin, Viktor P. Yakubovskyi, Tanner S. Blesener, Andrew T. Healy, David E. Herbert, David A. Blank, Victor N. Nemykin, Yuriy P. Kovtun

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Abstract

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.

Original languageEnglish (US)
Pages (from-to)5713-5718
Number of pages6
JournalOrganic Letters
Volume21
Issue number14
DOIs
StatePublished - Jul 8 2019

PubMed: MeSH publication types

  • Journal Article
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

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    Zatsikha, Y. V., Didukh, N. O., Swedin, R. K., Yakubovskyi, V. P., Blesener, T. S., Healy, A. T., Herbert, D. E., Blank, D. A., Nemykin, V. N., & Kovtun, Y. P. (2019). Preparation of Viscosity-Sensitive Isoxazoline/Isoxazolyl-Based Molecular Rotors and Directly Linked BODIPY-Fulleroisoxazoline from the Stable meso-(Nitrile Oxide)-Substituted BODIPY. Organic Letters, 21(14), 5713-5718. https://doi.org/10.1021/acs.orglett.9b02082