Pentafluorophenyl-tagged poly(2-isopropenyl-2-oxazoline) as a highly reactive precursor for para-fluoro-thiol click chemistry

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Pentafluorophenyl-tagged poly(2-isopropenyl-2-oxazoline) as a highly reactive precursor for para-fluoro-thiol click chemistry

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Pentafluorophenyl-tagged poly(2-isopropenyl-2-oxazoline) as a highly reactive precursor for para-fluoro-thiol click chemistry

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10404 - Polymer science

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2025

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Macromolecules

ISSN

0024-9297

e-ISSN

1520-5835

Svazek periodika

58

Číslo periodika v rámci svazku

21

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

15

Strana od-do

12011-12025

Kód UT WoS článku

001601157000001

EID výsledku v databázi Scopus

2-s2.0-105021239708