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

34 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

Publisher Copyright:
Copyright © 2019 American Chemical Society.

Access

10.1021/acs.orglett.9b02082

OpenUrl availability

Full text

Cite this

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

@article{70bea3dcb1d24c269d956dd93491d07c,

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

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 = "Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = jul,

day = "8",

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

language = "English (US)",

volume = "21",

pages = "5713--5718",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "14",

}

TY - JOUR

T1 - Preparation of Viscosity-Sensitive Isoxazoline/Isoxazolyl-Based Molecular Rotors and Directly Linked BODIPY-Fulleroisoxazoline from the Stable meso-(Nitrile Oxide)-Substituted BODIPY

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.

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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85069814550&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85069814550&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.9b02082

DO - 10.1021/acs.orglett.9b02082

M3 - Article

C2 - 31283252

AN - SCOPUS:85069814550

SN - 1523-7060

VL - 21

SP - 5713

EP - 5718

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

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

Abstract

Bibliographical note

Access

OpenUrl availability

Other files and links

Fingerprint

Cite this