Improved Performance of Protected Catecholic Polysiloxanes for Bioinspired Wet Adhesion to Surface Oxides

被引:102
作者
Heo, Jinhwa [1 ,2 ]
Kang, Taegon [1 ,2 ]
Jang, Se Gyu [1 ]
Hwang, Dong Soo [5 ]
Spruell, Jason M. [1 ]
Killops, Kato L. [7 ]
Waite, J. Herbert [1 ,3 ,4 ]
Hawker, Craig J. [1 ,2 ,3 ,6 ]
机构
[1] Univ Calif Santa Barbara, Mat Res Lab, Santa Barbara, CA 93106 USA
[2] Univ Calif Santa Barbara, Dept Mat, Santa Barbara, CA 93106 USA
[3] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
[4] Univ Calif Santa Barbara, Dept Mol Cell & Dev Biol, Santa Barbara, CA 93106 USA
[5] Pohang Univ Sci & Technol, Ocean Sci & Technol Inst, Pohang 790784, South Korea
[6] King Fahd Univ Petr & Minerals, Ctr Refining & Petrochem, Dhahran 31261, Saudi Arabia
[7] USA, Edgewood Chem Biol Ctr, Resarch Dev & Engn Command, Aberdeen Proving Ground, MD 21010 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
ENE CLICK CHEMISTRY; MUSSEL ADHESION; MYTILUS-EDULIS; ACID CATALYSTS; PROTEIN FILMS; LEWIS-ACID; L-DOPA; HYDROSILATION; LITHOGRAPHY; EFFICIENT;
D O I
10.1021/ja309044z
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A facile synthetic strategy for introducing catecholic moieties into polymeric materials based on a readily available precursor (eugenol) and efficient chemistries [tris-(pentafluorophenyl)borane-catalyzed silation and thiol-ene coupling] is reported. Silyl protection is shown to be critical for the oxidative stability of catecholic moieties during synthesis and processing, which allows functionalized polysiloxane derivatives to be fabricated into 3D microstructures as well as 2D patterned surfaces. Deprotection gives stable catechol surfaces whose adhesion to a variety of oxide surfaces can be precisely tuned by the level of catechol incorporation. The advantage of silyl protection for catechol-functionalized polysiloxanes is demonstrated and represents a promising and versatile new platform for underwater surface treatments.
引用
收藏
页码:20139 / 20145
页数:7
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