Mechanism-Based Fluorogenic trans-Cyclooctene-Tetrazine Cycloaddition
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F17%3A00475145" target="_blank" >RIV/61388963:_____/17:00475145 - isvavai.cz</a>
Result on the web
<a href="http://onlinelibrary.wiley.com/doi/10.1002/anie.201610491/full" target="_blank" >http://onlinelibrary.wiley.com/doi/10.1002/anie.201610491/full</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/anie.201610491" target="_blank" >10.1002/anie.201610491</a>
Alternative languages
Result language
angličtina
Original language name
Mechanism-Based Fluorogenic trans-Cyclooctene-Tetrazine Cycloaddition
Original language description
The development of fluorogenic reactions which lead to the formation of fluorescent products from two nonfluorescent starting materials is highly desirable, but challenging. Reported herein is a new concept of fluorescent product formation upon the inverse electron-demand Diels-Alder reaction of 1,2,4,5-tetrazines with particular trans-cyclo-octene (TCO) isomers. In sharp contrast to known fluorogenic reagents the presented chemistry leads to the rapid formation of unprecedented fluorescent 1,4-dihydropyridazines so that the fluorophore is built directly upon the chemical reaction. Attachment of an extra fluorophore moiety is therefore not needed. The photochemical properties of the resulting dyes can be easily tuned by changing the substitution pattern of the starting 1,2,4,5-tetrazine. We support the claim with NMR measurements and rationalize the data by computational study. Cell-labeling experiments were performed to demonstrate the potential of the fluorogenic reaction for bioimaging.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Angewandte Chemie - International Edition
ISSN
1433-7851
e-ISSN
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Volume of the periodical
56
Issue of the periodical within the volume
5
Country of publishing house
DE - GERMANY
Number of pages
4
Pages from-to
1334-1337
UT code for WoS article
000394997700027
EID of the result in the Scopus database
2-s2.0-85009823803