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Photoactivatable Fluorogens by Intramolecular C-H Insertion of Perfluoroaryl Azide
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.ORCID iD: 0000-0002-1533-6514
Univ Massachusetts Lowell, Dept Chem, Lowell, MA 01854 USA..ORCID iD: 0000-0003-1121-4007
2019 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 84, no 22, p. 14520-14528Article in journal (Refereed) Published
Abstract [en]

Molecules, capable of fluorescence turn-on by light, are highly sought-after in spatio-temporal labeling, surface patterning, monitoring cellular and molecular events, and high-resolution fluorescence imaging. In this work, we report a fluorescence turn-on system based on photoinitiated intramolecular C-H insertion of azide into the neighboring aromatic ring. The azide-masked fluorogens were efficiently synthesized via a cascade nucleophilic aromatic substitution of perfluoroaryl azides with carbazoles. The scaffold also allows for derivatization with biological ligands, as exemplified with D-mannose in this study. This photoinitiated intramolecular transformation led to high yields, high photo-conversion efficiency, and well-separated wavelengths for photoactivation and fluorescence excitation. The mannose-derivatized structure enabled spatio-temporal activation and showed high contrast and signal amplification. Live cell imaging suggested that the mannose-tagged fluorogen was transported to the lysosomes.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2019. Vol. 84, no 22, p. 14520-14528
National Category
Chemical Sciences
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URN: urn:nbn:se:kth:diva-269136DOI: 10.1021/acs.joc.9b02050ISI: 000497259900015PubMedID: 31589042Scopus ID: 2-s2.0-85074604850OAI: oai:DiVA.org:kth-269136DiVA, id: diva2:1414287
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QC 20200312

Available from: 2020-03-12 Created: 2020-03-12 Last updated: 2020-05-20Bibliographically approved

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Xie, ShengProietti, GiampieroRamström, Olof

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