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.
Bibliographical noteFunding 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.