Pentafluorophenyl-tagged poly(2-isopropenyl-2-oxazoline) as a highly reactive precursor for para-fluoro-thiol click chemistry
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389013%3A_____%2F25%3A00641189" target="_blank" >RIV/61389013:_____/25:00641189 - isvavai.cz</a>
Result on the web
<a href="https://pubs.acs.org/doi/10.1021/acs.macromol.5c02254" target="_blank" >https://pubs.acs.org/doi/10.1021/acs.macromol.5c02254</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.macromol.5c02254" target="_blank" >10.1021/acs.macromol.5c02254</a>
Alternative languages
Result language
angličtina
Original language name
Pentafluorophenyl-tagged poly(2-isopropenyl-2-oxazoline) as a highly reactive precursor for para-fluoro-thiol click chemistry
Original language description
Poly(2-isopropenyl-2-oxazoline) (PIPOx) is a versatile postpolymerization modification platform, yet its reactions have so far been limited to direct additions of thiols and carboxylic acids with variable efficiency. Here, we show that the reaction of PIPOx with 2,3,4,5,6-pentafluorothiophenol (PFTP) rapidly and cleanly generates poly(N-(2-((perfluorophenyl)thio)ethyl)methacrylamide) (PPFPTEMA), a highly reactive precursor for para-fluoro-thiol (PFT) click chemistry, featuring fast kinetics, equimolarity, orthogonality, and facile product isolation. A wide array of commercially available thiols react quantitatively and selectively with PPFPTEMA, enabling the synthesis of well-defined polymethacrylamides with diverse side-chain functionalities, including ionizable groups, supramolecular motifs, natural compounds, drugs, fluorescent tags, and polymers. The high efficiency and orthogonality of the PFT click reaction also allow multiple thiols to be combined to precisely tailor the copolymer composition. Importantly, when using thiol excess, the pentafluorophenyl groups in PPFPTEMA are found to undergo multiple substitutions under mild conditions, offering an unprecedented level of synthetic flexibility for designing functional polymers. Overall, this work seamlessly integrates PFT click chemistry into the PIPOx platform, establishing a powerful modular framework for the precision synthesis of multifunctional polymers.
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
10404 - Polymer science
Result continuities
Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Macromolecules
ISSN
0024-9297
e-ISSN
1520-5835
Volume of the periodical
58
Issue of the periodical within the volume
21
Country of publishing house
US - UNITED STATES
Number of pages
15
Pages from-to
12011-12025
UT code for WoS article
001601157000001
EID of the result in the Scopus database
2-s2.0-105021239708