Organic Letters

, том 20 , издание 14 , страницы 4213-4217

Fluorogenic Sydnone-Modified Coumarins Switched-On by Copper-Free Click Chemistry

Camille Favre ^{1, 2}

Frédéric Friscourt ^{1, 2}

Скрыть аффилиации авторов Показать аффилиации авторов: 2 аффилиации

Institut Européen de Chimie et Biologie, Université de Bordeaux, 2 rue Robert Escarpit, 33607 Pessac, France |

Institut de Neurosciences Cognitives et Intégratives d’Aquitaine, CNRS UMR5287, Bordeaux, France |

Тип публикации: Journal Article

Дата публикации: 2018-07-11

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

БС1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.8b01587

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PubMed ID: 29995429

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Краткое описание

The synthesis, photophysical characterization, and biochemical application of sydnone-modified coumarins, a novel class of fluorogenic clickable reagents, are reported. The sydnone moiety, a stable aromatic 1,3-dipole, efficiently quenched the fluorescence of coumarin, which could be restored, with a 132-fold enhancement, upon cycloadditions with cyclooctynes, thereby expanding the fluorogenic click toolbox. TD-DFT calculations suggest that the fluorescence quenching of the sydnone-modified coumarins is likely due to the presence of an energetically low-lying nonemissive charge-separated state.

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Favre C. et al. Fluorogenic Sydnone-Modified Coumarins Switched-On by Copper-Free Click Chemistry // Organic Letters. 2018. Vol. 20. No. 14. pp. 4213-4217.

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Favre C., Friscourt F. Fluorogenic Sydnone-Modified Coumarins Switched-On by Copper-Free Click Chemistry // Organic Letters. 2018. Vol. 20. No. 14. pp. 4213-4217.

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TY - JOUR

DO - 10.1021/acs.orglett.8b01587

UR - https://doi.org/10.1021/acs.orglett.8b01587

TI - Fluorogenic Sydnone-Modified Coumarins Switched-On by Copper-Free Click Chemistry

T2 - Organic Letters

AU - Favre, Camille

AU - Friscourt, Frédéric

PY - 2018

DA - 2018/07/11

PB - American Chemical Society (ACS)

SP - 4213-4217

IS - 14

VL - 20

PMID - 29995429

SN - 1523-7060

SN - 1523-7052

ER -

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@article{2018_Favre,

author = {Camille Favre and Frédéric Friscourt},

title = {Fluorogenic Sydnone-Modified Coumarins Switched-On by Copper-Free Click Chemistry},

journal = {Organic Letters},

year = {2018},

volume = {20},

publisher = {American Chemical Society (ACS)},

month = {jul},

url = {https://doi.org/10.1021/acs.orglett.8b01587},

number = {14},

pages = {4213--4217},

doi = {10.1021/acs.orglett.8b01587}

}

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Favre, Camille, et al. “Fluorogenic Sydnone-Modified Coumarins Switched-On by Copper-Free Click Chemistry.” Organic Letters, vol. 20, no. 14, Jul. 2018, pp. 4213-4217. https://doi.org/10.1021/acs.orglett.8b01587.