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

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

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

Bibliographical note

Funding Information:
Generous support from the Minnesota Supercomputing Institute, NSERC, CFI, NSF (CHE-1464711), the University of Manitoba, and WestGrid Canada to V.N.N. is greatly appreciated. Generous support from the NSF support (DMR-1708177) to D.A.B. is greatly appreciated. Generous support from NAS of Ukraine to Y.P.K. is greatly appreciated.

Publisher Copyright:
Copyright © 2019 American Chemical Society.

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