Spatial and Temporal Control of Thiol-Michael Addition Via Photocaged Superbase in Photopatterning and Two-Stage Polymer Networks Formation

Overview

Journal Macromolecules

Date 2014 Sep 30

PMID 25264379

Citations 25

Authors

Weixian Xi

Haiyan Peng

Alan Aguirre-Soto

Christopher J Kloxin

Jeffery W Stansbury

Christopher N Bowman

Affiliations

Soon will be listed here.

Abstract

Photochemical processes enable spatial and temporal control of reactions, which can be implemented as an accurate external control approach in both polymer synthesis and materials applications. "Click" reactions have also been employed as efficient tools in the same field. Herein, we combined photochemical processes and thiol-Michael "click" reactions to achieve a "photo-click" reaction that can be used in surface patterning and controlled polymer network formation, owing to the ease of spatial and temporal control through use of photolabile amines as appropriate catalysts.

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References

Stoll R, Hecht S . Artificial light-gated catalyst systems. Angew Chem Int Ed Engl. 2010; 49(30):5054-75. DOI: 10.1002/anie.201000146. View

Tucker-Schwartz A, Farrell R, Garrell R . Thiol-ene click reaction as a general route to functional trialkoxysilanes for surface coating applications. J Am Chem Soc. 2011; 133(29):11026-9. DOI: 10.1021/ja202292q. View

Pauloehrl T, Delaittre G, Winkler V, Welle A, Bruns M, Borner H . Adding spatial control to click chemistry: phototriggered Diels-Alder surface (bio)functionalization at ambient temperature. Angew Chem Int Ed Engl. 2011; 51(4):1071-4. DOI: 10.1002/anie.201107095. View

Rodriguez-Emmenegger C, Preuss C, Yameen B, Pop-Georgievski O, Bachmann M, Mueller J . Controlled cell adhesion on poly(dopamine) interfaces photopatterned with non-fouling brushes. Adv Mater. 2013; 25(42):6123-7. DOI: 10.1002/adma.201302492. View

Rostovtsev V, Green L, Fokin V, Sharpless K . A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew Chem Int Ed Engl. 2002; 41(14):2596-9. DOI: 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4. View

Pauloehrl T, Welle A, Bruns M, Linkert K, Borner H, Bastmeyer M . Spatially controlled surface immobilization of nonmodified peptides. Angew Chem Int Ed Engl. 2013; 52(37):9714-8. DOI: 10.1002/anie.201302040. View

Iha R, Wooley K, Nystrom A, Burke D, Kade M, Hawker C . Applications of orthogonal "click" chemistries in the synthesis of functional soft materials. Chem Rev. 2009; 109(11):5620-86. PMC: 3165017. DOI: 10.1021/cr900138t. View

Adzima B, Tao Y, Kloxin C, DeForest C, Anseth K, Bowman C . Spatial and temporal control of the alkyne-azide cycloaddition by photoinitiated Cu(II) reduction. Nat Chem. 2011; 3(3):256-59. DOI: 10.1038/nchem.980. View

Kloxin C, Scott T, Park H, Bowman C . Mechanophotopatterning on a photoresponsive elastomer. Adv Mater. 2011; 23(17):1977-81. DOI: 10.1002/adma.201100323. View

10.

Song W, Wang Y, Qu J, Madden M, Lin Q . A photoinducible 1,3-dipolar cycloaddition reaction for rapid, selective modification of tetrazole-containing proteins. Angew Chem Int Ed Engl. 2008; 47(15):2832-5. DOI: 10.1002/anie.200705805. View

11.

Arumugam S, Popik V . Patterned surface derivatization using Diels-Alder photoclick reaction. J Am Chem Soc. 2011; 133(39):15730-6. DOI: 10.1021/ja205652m. View

12.

Tornoe C, Christensen C, Meldal M . Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J Org Chem. 2002; 67(9):3057-64. DOI: 10.1021/jo011148j. View

13.

Gruendling T, Oehlenschlaeger K, Frick E, Glassner M, Schmid C, Barner-Kowollik C . Rapid UV light-triggered macromolecular click conjugations via the use of o-quinodimethanes. Macromol Rapid Commun. 2011; 32(11):807-12. DOI: 10.1002/marc.201100159. View

14.

Hoyle C, Bowman C . Thiol-ene click chemistry. Angew Chem Int Ed Engl. 2010; 49(9):1540-73. DOI: 10.1002/anie.200903924. View

15.

Kolb H, Finn M, Sharpless K . Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew Chem Int Ed Engl. 2001; 40(11):2004-2021. DOI: 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5. View

16.

Poloukhtine A, Mbua N, Wolfert M, Boons G, Popik V . Selective labeling of living cells by a photo-triggered click reaction. J Am Chem Soc. 2009; 131(43):15769-76. PMC: 2776736. DOI: 10.1021/ja9054096. View

17.

Pauloehrl T, Delaittre G, Bruns M, Meissler M, Borner H, Bastmeyer M . (Bio)molecular surface patterning by phototriggered oxime ligation. Angew Chem Int Ed Engl. 2012; 51(36):9181-4. DOI: 10.1002/anie.201202684. View

18.

Tischer T, Claus T, Bruns M, Trouillet V, Linkert K, Rodriguez-Emmenegger C . Spatially controlled photochemical peptide and polymer conjugation on biosurfaces. Biomacromolecules. 2013; 14(12):4340-50. DOI: 10.1021/bm401274v. View

19.

Tasdelen M, Yagci Y . Light-induced click reactions. Angew Chem Int Ed Engl. 2013; 52(23):5930-8. DOI: 10.1002/anie.201208741. View

20.

Bauer D, Rogge A, Stolzer L, Barner-Kowollik C, Fruk L . Light induced DNA-protein conjugation. Chem Commun (Camb). 2013; 49(77):8626-8. DOI: 10.1039/c3cc43291b. View