Selective and Orthogonal Post-Polymerization Modification using Sulfur(VI) Fluoride Exchange (SuFEx) and Copper-Catalyzed Azide-Alkyne Cycloaddition (CuAAC) Reactions

被引：84

作者：

Oakdale, James S. ^{[2
]}

Kwisnek, Luke ^{[3
]}

Fokin, Valery V. ^{[1
]}

机构：

[1] Univ So Calif, Bridge, 837 Bloom Walk, Los Angeles, CA 90089 USA

[2] Lawrence Livermore Natl Lab, Div Mat Sci, 7000 East Ave, Livermore, CA 94550 USA

[3] DSM Funct Mat, 1122 St Charles St, Elgin, IL 60120 USA

来源：

MACROMOLECULES | 2016年 / 49卷 / 12期

基金：

美国国家科学基金会;

关键词：

CLICK CHEMISTRY; POSTPOLYMERIZATION MODIFICATION; ARYL FLUOROSULFONATES; COUPLING REACTIONS; DIELS-ALDER; COPOLYMERS; POLYMERS; SURFACE; ENE;

D O I：

10.1021/acs.macromol.6b00101

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

Functional polystyrenes and polyacrylamides, containing combinations of fluorosulfate, aromatic silyl ether, and azide side chains, were used as scaffolds to demonstrate the postpolymerization modification capabilities of sulfur(VI) fluoride exchange (SuFEx) and CuAAC chemistries. Fluorescent dyes bearing appropriate functional groups were sequentially attached to the backbone of the copolymers, quantitatively and selectively addressing their reactive partners. This combined SuFEx and CuAAC approach proved to be robust and versatile, allowing for a rare accomplishment: triple orthogonal functionalization of a copolymer under essentially ambient conditions without protecting groups.

引用

页码：4473 / 4479

页数：7

共 40 条

[1] A Dynamic Duo: Pairing Click Chemistry and Postpolymerization Modification To Design Complex Surfaces [J].

Arnold, Rachelle M. ;

Patton, Derek L. ;

Popik, Vladimir V. ;

Locklin, Jason .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (10) :2999-3008

[2] Facile routes to patterned surface neutralization layers for block copolymer lithography [J].

Bang, Joona ;

Bae, Joonwon ;

Lowenhielm, Peter ;

Spiessberger, Christian ;

Given-Beck, Susan A. ;

Russell, Thomas P. ;

Hawker, Craig J. .

ADVANCED MATERIALS, 2007, 19 (24) :4552-+

[3] Clicking Pentafluorostyrene Copolymers: Synthesis, Nanoprecipitation, and Glycosylation [J].

Becer, C. Remzi ;

Babiuch, Krzysztof ;

Pilz, David ;

Hornig, Stephanie ;

Heinze, Thomas ;

Gottschaldt, Michael ;

Schubert, Ulrich S. .

MACROMOLECULES, 2009, 42 (07) :2387-2394

[4] 'Click' chemistry in polymer and materials science [J].

Binder, Wolfgang H. ;

Sachsenhofer, Robert .

MACROMOLECULAR RAPID COMMUNICATIONS, 2007, 28 (01) :15-54

[5] Development of thermal and photochemical strategies for thiol-ene click polymer functionalization [J].

Campos, Luis M. ;

Killops, Kato L. ;

Sakai, Ryosuke ;

Paulusse, Jos M. J. ;

Damiron, Denis ;

Drockenmuller, Eric ;

Messmore, Benjamin W. ;

Hawker, Craig J. .

MACROMOLECULES, 2008, 41 (19) :7063-7070

[6]

Chen XY, 1999, J POLYM SCI POL CHEM, V37, P627, DOI 10.1002/(SICI)1099-0518(19990301)37:5<627::AID-POLA13>3.0.CO

[7]

2-Q

[8] NEW SYNTHESES OF ARYL FLUORIDES AND ARYL FLUOROSULFONATES FROM OXYFLUORIDES OF SULFUR [J].

CRAMER, R ;

COFFMAN, DD .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (10) :4164-&

[9]

Dong J., 2014, ANGEW CHEM INT ED, V53, P9466

[10] Sulfur(VI) Fluoride Exchange (SuFEx): Another Good Reaction for Click Chemistry [J].

Dong, Jiajia ;

Krasnova, Larissa ;

Finn, M. G. ;

Sharpless, K. Barry .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) :9430-9448

← 1 2 3 4 →