TY - JOUR
T1 - A Straightforward Method for Fluorinated Polythioether Synthesis
AU - Daglar, Ozgun
AU - Cakmakci, Emrah
AU - Gunay, Ufuk Saim
AU - Hizal, Gurkan
AU - Tunca, Umit
AU - Durmaz, Hakan
N1 - Publisher Copyright:
© 2020 American Chemical Society.
PY - 2020/4/28
Y1 - 2020/4/28
N2 - The synthesis of fluorinated polymers via efficient routes along with mild experimental conditions is always desirable in terms of synthetic polymer chemistry. In this work, a straightforward method for fluorinated polythioether synthesis was developed. A commercially available electron-deficient alkyne compound, namely 4,4,4-trifluoro-2-butynoate (1), linked to both trifluoromethyl (CF3) and ester units was polymerized with various dithiols by using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as a catalyst at room temperature, yielding CF3-substituted polythioethers (CF3-polythioethers). Unlike common polymerization methods (anionic and radical) described in the literature, which include harsh conditions to produce CF3-substituted polymers, the synthetic methodology followed in this study offers mild conditions, and CF3-polythioethers with high molecular weights (Mw, up to 21.1 kDa in 1 min and up to 42.5 kDa in 1 h) were obtained in high yields in reasonably short durations. The judicious combination of polythioether chemistry with a rapid polymerization method was introduced in this study to open a way for the development of novel fluorinated polymeric materials.
AB - The synthesis of fluorinated polymers via efficient routes along with mild experimental conditions is always desirable in terms of synthetic polymer chemistry. In this work, a straightforward method for fluorinated polythioether synthesis was developed. A commercially available electron-deficient alkyne compound, namely 4,4,4-trifluoro-2-butynoate (1), linked to both trifluoromethyl (CF3) and ester units was polymerized with various dithiols by using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) as a catalyst at room temperature, yielding CF3-substituted polythioethers (CF3-polythioethers). Unlike common polymerization methods (anionic and radical) described in the literature, which include harsh conditions to produce CF3-substituted polymers, the synthetic methodology followed in this study offers mild conditions, and CF3-polythioethers with high molecular weights (Mw, up to 21.1 kDa in 1 min and up to 42.5 kDa in 1 h) were obtained in high yields in reasonably short durations. The judicious combination of polythioether chemistry with a rapid polymerization method was introduced in this study to open a way for the development of novel fluorinated polymeric materials.
UR - http://www.scopus.com/inward/record.url?scp=85083828471&partnerID=8YFLogxK
U2 - 10.1021/acs.macromol.0c00548
DO - 10.1021/acs.macromol.0c00548
M3 - Article
AN - SCOPUS:85083828471
SN - 0024-9297
VL - 53
SP - 2965
EP - 2975
JO - Macromolecules
JF - Macromolecules
IS - 8
ER -