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)

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

26 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

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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10.1021/acs.orglett.9b02082

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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.",

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

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 {\textcopyright} 2019 American Chemical Society.",

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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.

N1 - 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.

PY - 2019/7/8

Y1 - 2019/7/8

N2 - 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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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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