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

doi:10.1021/acs.orglett.9b02082

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

Chemistry (Twin Cities)

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39 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 language	English (US)
Pages (from-to)	5713-5718
Number of pages	6
Journal	Organic Letters
Volume	21
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.9b02082
State	Published - Jul 8 2019

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Copyright © 2019 American Chemical Society.

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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

Preparation of Viscosity-Sensitive Isoxazoline/Isoxazolyl-Based Molecular Rotors and Directly Linked BODIPY-Fulleroisoxazoline from the Stable meso-(Nitrile Oxide)-Substituted BODIPY. / Zatsikha, Yuriy V.; Didukh, Natalia O.; Swedin, Rachel K et al.
In: Organic Letters, Vol. 21, No. 14, 08.07.2019, p. 5713-5718.

Research output: Contribution to journal › Article › peer-review

Zatsikha, YV, Didukh, NO, Swedin, RK, Yakubovskyi, VP, Blesener, TS, Healy, AT, Herbert, DE, Blank, DA, Nemykin, VN & Kovtun, YP 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, vol. 21, no. 14, pp. 5713-5718. https://doi.org/10.1021/acs.orglett.9b02082

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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.",

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year = "2019",

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doi = "10.1021/acs.orglett.9b02082",

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AU - Zatsikha, Yuriy V.

AU - Didukh, Natalia O.

AU - Swedin, Rachel K

AU - Yakubovskyi, Viktor P.

AU - Blesener, Tanner S.

AU - Healy, Andrew T.

AU - Herbert, David E.

AU - Blank, David A.

AU - Nemykin, Victor N.

AU - Kovtun, Yuriy P.

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

Abstract

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