2.6 CuAAC Applications in Macromolecules, Polymers, Nanoparticles, and Supramolecular Chemistry

C. Zhang; K. M. Page; J. C. M. van Hest

doi:10.1055/sos-SD-235-00101

Teilen / Bookmarken

Facebook X Linkedin Weibo

PDF herunterladen

Rutjes, F. P. J. T. : 2022 Science of Synthesis, 2021/4: Click Chemistry DOI: 10.1055/sos-SD-235-00101

Click Chemistry

2.6 CuAAC Applications in Macromolecules, Polymers, Nanoparticles, and Supramolecular Chemistry

Weitere Informationen

Buch

Herausgeber: Rutjes, F. P. J. T.

Autoren: Agrahari, A. K.; Alabugin, I. V. ; Beke-Somfai, T. ; Blanco-Ania, D. ; Bratlie, K. M. ; Carlson, J. C. T. ; Friscourt, F. ; Giel, M.-C. ; Harris, T. ; Houk, K. N. ; Janssen, L. J. N.; Kacprzak, K. M.; Kann, N. ; Kovalová, A.; Kuba, W. ; La Venia, A.; Liskamp, R. M. J. ; Meuleman, T. J.; Mikula, H. ; Mishra, A.; Moses, J. E. ; Ort, F. F.; Page, K. M.; Paterson, A. J. ; Rutkowski, J.; Singh, R.; Sinha, A. K.; Skiera, I.; Smedley, C. J. ; Svatunek, D. ; Tiwari, V. K. ; van Hest, J. C. M. ; Vrabel, M. ; Wilkovitsch, M. ; Xu, Z.; Zhang, C.

Titel: Click Chemistry

Print ISBN: 9783132435568; Online ISBN: 9783132435575; Buch-DOI: 10.1055/b000000077

1st edition © 2022. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Fachgebiete: Organische Chemie;Chemische Reaktionen, Katalyse;Organometallchemie;Chemische Labormethoden, Stöchiometrie

Science of Synthesis Reference Libraries

Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Reihenherausgeber: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Typ: Mehrbändiges Werk

Auch verfügbar auf

Vorschau
Abstract
Volltext
Referenzen
Zusatzmaterial

Abstract

In this chapter we describe applications of copper-catalyzed azide–alkyne cycloaddition (CuAAC) in macromolecular synthesis and polymer functionalization. This entails the synthesis of polymers with different architectures and the conjugation of polymers to surfaces and particles.

Schlüsselwörter

click chemistry - copper-catalyzed azide–alkyne cycloaddition (CuAAC) - alkynes - azides - biomimetic synthesis - copper catalysts - cycloaddition - dendrimers - macrocycles - medicinal chemistry - nanostructures - polymerization - polymers - supramolecular chemistry

1 Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed.. 2001; 40: 2004

Google Scholar

2 Meldal M, Tornøe CW. Chem. Rev.. 2008; 108: 2952

Google Scholar

3 Tornøe CW, Christensen C, Meldal M. J. Org. Chem.. 2002; 67: 3057

Google Scholar

4 Tornøe CW, Meldal M, Peptides: The Wave of the Future; Proceedings of the 2nd International and the 17th American Peptide Symposium. Houghten RA, Lebl M. Springer; Dordrecht, The Netherlands 2001. p 263.

Google Scholar

5 Zhang L, Chen X, Xue P, Sun HHY, Williams ID, Sharpless KB, Fokin VV, Jia G. J. Am. Chem. Soc.. 2005; 127: 15998

Google Scholar

6 Wu P, Feldman AK, Nugent AK, Hawker CJ, Scheel A, Voit B, Pyun J, Fréchet JMJ, Sharpless KB, Fokin VV. Angew. Chem. Int. Ed.. 2004; 43: 3928

Google Scholar

7 Kolb HC, Sharpless KB. Drug Discovery Today. 2003; 8: 1128

Google Scholar

8 Rostovtsev VV, Green LG, Fokin VV, Sharpless KB. Angew. Chem. Int. Ed.. 2002; 41: 2596

Google Scholar

9 Huisgen R, Szeimies G, Möbius L. Chem. Ber.. 1967; 100: 2494

Google Scholar

10 1,3-Dipolar Cycloaddition Chemistry. Padwa A. Wiley; New York 1984

Google Scholar

11 Barner-Kowollik C, Du Prez FE, Espeel P, Hawker CJ, Junkers T, Schlaad H, Van Camp W. Angew. Chem. Int. Ed.. 2011; 50: 60

Google Scholar

12 Hein JE, Fokin VV. Chem. Soc. Rev.. 2010; 39: 1302

Google Scholar

13 Himo F, Lovell T, Hilgraf R, Rostovtsev VV, Noodleman L, Sharpless KB, Fokin VV. J. Am. Chem. Soc.. 2005; 127: 210

Google Scholar

14 Appukkuttan P, Dehaen W, Fokin VV, Van der Eycken E. Org. Lett.. 2004; 6: 4223

Google Scholar

15 Golas PL, Tsarevsky NV, Sumerlin BS, Matyjaszewski K. Macromolecules. 2006; 39: 6451

Google Scholar

16 Neumann S, Biewend M, Rana S, Binder WH. Macromol. Rapid Commun.. 2020; 41: 1900 359

Google Scholar

17 Arslan M, Acik G, Tasdelen MA. Polym. Chem.. 2019; 10: 3806

Google Scholar

18 Earla A, Braslau R. Macromol. Rapid Commun.. 2014; 35: 666

Google Scholar

19 Zhao B, Gao Z, Zheng Y, Gao C. J. Am. Chem. Soc.. 2019; 141: 4541

Google Scholar

20 Martens S, Holloway JO, Du Prez FE. Macromol. Rapid Commun.. 2017; 38: 1700 469

Google Scholar

21 Yang C, Flynn JP, Niu J. Angew. Chem. Int. Ed.. 2018; 57: 16194

Google Scholar

22 Dai Y, Chen X, Zhang X. Polym. Chem.. 2019; 10: 34

Google Scholar

23 Kaufmann T, Gokmen MT, Rinnen S, Arlinghaus HF, Du Prez F, Ravoo BJ. J. Mater. Chem.. 2012; 22: 6190

Google Scholar

24 Li N, Binder WH. J. Mater. Chem.. 2011; 21: 16717

Google Scholar

25 Mansfeld U, Pietsch C, Hoogenboom R, Becer CR, Schubert US. Polym. Chem.. 2010; 1: 1560

Google Scholar

26 Lutz J.-F. Angew. Chem. Int. Ed.. 2007; 46: 1018

Google Scholar

27 Wolfgang HB. Macromol. Rapid Commun.. 2007; 28: 15

Google Scholar

28 Iha RK, Wooley KL, Nystrom AM, Burke DJ, Kade MJ, Hawker CJ. Chem. Rev.. 2009; 109: 5620

Google Scholar

29 Ouchi M, Terashima T, Sawamoto M. Chem. Rev.. 2009; 109: 4963

Google Scholar

30 Becer CR, Hoogenboom R, Schubert US. Angew. Chem. Int. Ed.. 2009; 48: 4900

Google Scholar

31 Sumerlin BS, Vogt AP. Macromolecules. 2010; 43: 1

Google Scholar

32 Khanna K, Varshney S, Kakkar A. Macromolecules. 2010; 43: 5688

Google Scholar

33 Golas PL, Matyjaszewski K. Chem. Soc. Rev.. 2010; 39: 1338

Google Scholar

34 Franc G, Kakkar AK. Chem.–Eur. J.. 2009; 15: 5630

Google Scholar

35 Lecomte P, Riva R, Jérôme C, Jérôme R. Macromol. Rapid Commun.. 2008; 29: 982

Google Scholar

36 Johnson JA, Finn MG, Koberstein JT, Turro NJ. Macromol. Rapid Commun.. 2008; 29: 1052

Google Scholar

37 Nandivada H, Jiang X, Lahann J. Adv. Mater. (Weinheim, Ger.). 2007; 19: 2197

Google Scholar

38 Franc G, Kakkar AK. Chem. Soc. Rev.. 2010; 39: 1536

Google Scholar

39 Opsteen JA, van Hest JCM. Chem. Commun. (Cambridge). 2005; 57

Google Scholar

40 Durmaz H, Dag A, Altintas O, Erdogan T, Hizal G, Tunca U. Macromolecules. 2007; 40: 191

Google Scholar

41 Altintas O, Tunca U. Chem.–Asian J.. 2011; 6: 2584

Google Scholar

42 Lallana E, Fernandez-Trillo F, Sousa-Herves A, Riguera R, Fernandez-Megia E. Pharm. Res.. 2012; 29: 902

Google Scholar

43 Parrish B, Breitenkamp RB, Emrick T. J. Am. Chem. Soc.. 2005; 127: 7404

Google Scholar

44 Strutt NL, Zhang H, Giesener MA, Lei J, Stoddart JF. Chem. Commun. (Cambridge). 2012; 48: 1647

Google Scholar

45 Bu H.-B, Götz G, Reinold E, Vogt A, Schmid S, Segura JL, Blanco R, Gómez R, Bäuerle P. Tetrahedron. 2011; 67: 1114

Google Scholar

46 Ashton PR, Baxter I, Cantrill SJ, Fyfe MCT, Glink PT, Stoddart JF, White AJP, Williams DJ. Angew. Chem. Int. Ed.. 1998; 37: 1294

Google Scholar

47 Miyauchi M, Harada A. J. Am. Chem. Soc.. 2004; 126: 11418

Google Scholar

48 Wong C.-H, Zimmerman SC. Chem. Commun. (Cambridge). 2013; 49: 1679

Google Scholar

49 Macrocycles. Weber E, Vögtle F. Springer; Berlin 1992

Google Scholar

50 Lehn J.-M. Science (Washington, D. C.). 1993; 260: 1762

Google Scholar

51 Schulz M, Christoffers J. Tetrahedron. 2013; 69: 802

Google Scholar

52 Hradilová L, Grepl M, Dvořáková B, Hradil P. Tetrahedron Lett.. 2013; 54: 1218

Google Scholar

53 Jenkins A, Kratochvíl P, Stepto R, Suter U. Pure Appl. Chem.. 1996; 68: 2287

Google Scholar

54 Sharma AK, Cornaggia C, Pasini D. Macromol. Chem. Phys.. 2010; 211: 2254

Google Scholar

55 Edizer S, Veronesi B, Karahan O, Aviyente V, Değirmenci I, Galbiati A, Pasini D. Macromolecules. 2009; 42: 1860

Google Scholar

56 Coluccini C, Metrangolo P, Parachini M, Pasini D, Resnati G, Righetti P. J. Polym. Sci., Part A: Polym. Chem.. 2008; 46: 5202

Google Scholar

57 Cagnoni E, Pasini D, Galbiati A, Ricci M, Righetti P. Macromolecules. 2003; 36: 8894

Google Scholar

58 Blazquez E, Mustarelli P, Pasini D, Righetti P, Tomasi C. J. Mater. Chem.. 2004; 14: 2524

Google Scholar

59 Fox ME, Szoka FC, Fréchet JMJ. Acc. Chem. Res.. 2009; 42: 1141

Google Scholar

60 Laurent BA, Grayson SM. J. Am. Chem. Soc.. 2006; 128: 4238

Google Scholar

61 Pasini D. Molecules. 2013; 18: 9512

Google Scholar

62 Wang Q. Ph.D. Dissertation, Aix-Marseille Université,. 2012

Google Scholar

63 Shiao TC, Roy R. New J. Chem.. 2012; 36: 324

Google Scholar

64 Roy R, Chieh Shiao T. Chimia. 2011; 65: 24

Google Scholar

65 Roy R, Shiao TC, Rittenhouse-Olson K. Braz. J. Pharm. Sci.. 2013; 49: 85

Google Scholar

66 Meldal M. Macromol. Rapid Commun.. 2008; 29: 1016

Google Scholar

67 Lee J.-W, Kim B.-K, Jin S.-H. Bull. Korean Chem. Soc.. 2005; 26: 833

Google Scholar

68 Lee J.-W, Kim B.-K. Bull. Korean Chem. Soc.. 2005; 26: 658

Google Scholar

69 Lee JW, Kim JH, Kim B.-K, Shin WS, Jin S.-H. Tetrahedron. 2006; 62: 894

Google Scholar

70 Bakbak S, Leech PJ, Carson BE, Saxena S, King WP, Bunz UH. Macromolecules. 2006; 39: 6793

Google Scholar

71 Lee JW, Kim JH, Kim B.-K, Kim JH, Shin WS, Jin S.-H, Kim M. Bull. Korean Chem. Soc.. 2006; 27: 1795

Google Scholar

72 Lee JW, Kim B.-K, Kim HJ, Han SC, Shin WS, Jin S.-H. Macromolecules. 2006; 39: 2418

Google Scholar

73 Lee JW, Kim JH, Kim B.-K, Kim JH, Shin WS, Jin S.-H. Tetrahedron. 2006; 62: 9193

Google Scholar

74 Lee JW, Kim JH, Kim B.-K. Tetrahedron Lett.. 2006; 47: 2683

Google Scholar

75 IJsselstijn M, Cintrat J.-C. Tetrahedron. 2006; 62: 3837

Google Scholar

76 Lee JW, Kim B.-K, Kim JH, Shin WS, Jin S.-H. J. Org. Chem.. 2006; 71: 4988

Google Scholar

77 Sharma R, Naresh K, Chabre YM, Rej R, Saadeh NK, Roy R. Polym. Chem.. 2014; 5: 4321

Google Scholar

78 Liu F.-T, Rabinovich GA. Nat. Rev. Cancer. 2005; 5: 29

Google Scholar

79 Salatino M, Croci DO, Bianco GA, Ilarregui JM, Toscano MA, Rabinovich GA. Expert Opin. Biol. Ther.. 2008; 8: 45

Google Scholar

80 Hoare TR, Kohane DS. Polymer. 2008; 49: 1993

Google Scholar

81 Ossipov DA, Hilborn J. Macromolecules. 2006; 39: 1709

Google Scholar

82 Malkoch M, Vestberg R, Gupta N, Mespouille L, Dubois P, Mason AF, Hedrick JL, Liao Q, Frank CW, Kingsbury K, Hawker CJ. Chem. Commun. (Cambridge). 2006; 2774

Google Scholar

83 Lutz J.-F, Zarafshani Z. Adv. Drug Delivery Rev.. 2008; 60: 958

Google Scholar

84 Finetti C, Sola L, Elliott J, Chiari M. J. Chromatogr. A. 2017; 1513: 226

Google Scholar

85 Pickens CJ, Johnson SN, Pressnall MM, Leon MA, Berkland CJ. Bioconjugate Chem.. 2018; 29: 686

Google Scholar

86 Hong V, Presolski SI, Ma C, Finn MG. Angew. Chem. Int. Ed.. 2009; 48: 9879

Google Scholar

87 Besanceney-Webler C, Jiang H, Zheng T, Feng L, Soriano del Amo D, Wang W, Klivansky LM, Marlow FL, Liu Y, Wu P. Angew. Chem. Int. Ed.. 2011; 50: 8051

Google Scholar

88 Nair DP, Podgórski M, Chatani S, Gong T, Xi W, Fenoli CR, Bowman CN. Chem. Mater.. 2014; 26: 724

Google Scholar

89 Lutz J.-F, Börner HG. Prog. Polym. Sci.. 2008; 33: 1

Google Scholar

90 Duncan R. Nat. Rev. Drug Discovery. 2003; 2: 347

Google Scholar

91 Veronese FM. Biomaterials. 2001; 22: 405

Google Scholar

92 Pasut G, Veronese FM. Adv. Polym. Sci.. 2006; 192: 95

Google Scholar

93 Veronese FM, Harris JM. Adv. Drug Delivery Rev.. 2002; 54: 453

Google Scholar

94 Gil ES, Hudson SM. Prog. Polym. Sci.. 2004; 29: 1173

Google Scholar

95 Galaev IY, Mattiasson B. Trends Biotechnol.. 1999; 17: 335

Google Scholar

96 Hoffman AS, Stayton PS. Macromol. Symp.. 2004; 207: 139

Google Scholar

97 Hilbrig F, Freitag R. J. Chromatogr. B: Anal. Technol. Biomed. Life Sci.. 2003; 790: 79

Google Scholar

98 Ding Z, Long CJ, Hayashi Y, Bulmus EV, Hoffman AS, Stayton PS. Bioconjugate Chem.. 1999; 10: 395

Google Scholar

99 Chen J, Venkatesan H, Hu J. Adv. Eng. Mater.. 2018; 20: 1700 961

Google Scholar

100 Hardy JG, Pfaff A, Leal-Egaña A, Müller AH, Scheibel TR. Macromol. Biosci.. 2014; 14: 936

Google Scholar

101 Dirks AJT, van Berkel SS, Hatzakis NS, Opsteen JA, van Delft FL, Cornelissen JJLM, Rowan AE, van Hest JCM, Rutjes FPJT, Nolte RJM. Chem. Commun. (Cambridge). 2005; 4172

Google Scholar

102 Lutz J.-F, Börner HG, Weichenhan K. Macromol. Rapid Commun.. 2005; 26: 514

Google Scholar

103 Dirk T, Esse GW, Hans J, Rob M. Chem. Commun. (Cambridge). 2005; 4581

Google Scholar

104 Lutz J.-F, Börner HG, Weichenhan K. Macromolecules. 2006; 39: 6376

Google Scholar

105 Fernandez-Megia E, Correa J, Rodríguez-Meizoso I, Riguera R. Macromolecules. 2006; 39: 2113

Google Scholar

106 Ladmiral V, Mantovani G, Clarkson GJ, Cauet S, Irwin JL, Haddleton DM. J. Am. Chem. Soc.. 2006; 128: 4823

Google Scholar

107 Wu P, Malkoch M, Hunt JN, Vestberg R, Kaltgrad E, Finn MG, Fokin VV, Sharpless KB, Hawker CJ. Chem. Commun. (Cambridge). 2005; 5775

Google Scholar

108 Deiters A, Cropp TA, Mukherji M, Chin JW, Anderson JC, Schultz PG. J. Am. Chem. Soc.. 2003; 125: 11782

Google Scholar

109 Link AJ, Tirrell DA. J. Am. Chem. Soc.. 2003; 125: 11164

Google Scholar

110 Wang Q, Chan TR, Hilgraf R, Fokin VV, Sharpless KB, Finn MG. J. Am. Chem. Soc.. 2003; 125: 3192

Google Scholar

111 Link AJ, Vink MKS, Tirrell DA. J. Am. Chem. Soc.. 2004; 126: 10598

Google Scholar

112 Nischan N, Hackenberger CP. J. Org. Chem.. 2014; 79: 10727

Google Scholar

113 Deiters A, Cropp TA, Summerer D, Mukherji M, Schultz PG. Bioorg. Med. Chem. Lett.. 2004; 14: 5743

Google Scholar

114 Kiick KL, Saxon E, Tirrell DA, Bertozzi CR. Proc. Natl. Acad. Sci. U. S. A.. 2002; 99: 19

Google Scholar

115 Nairn NW, Shanebeck KD, Wang A, Graddis TJ, VanBrunt MP, Thornton KC, Grabstein K. Bioconjugate Chem.. 2012; 23: 2087

Google Scholar

116 Mehanna MM, Mohyeldin SM, Elgindy NA. J. Controlled Release. 2014; 187: 183

Google Scholar

117 Rytting E, Nguyen J, Wang X, Kissel T. Expert Opin. Drug Delivery. 2008; 5: 629

Google Scholar

118 Kreuter J. Adv. Drug Delivery Rev.. 2014; 71: 2

Google Scholar

119 Rao JP, Geckeler KE. Prog. Polym. Sci.. 2011; 36: 887

Google Scholar

120 Vauthier C, Polymer Nanoparticles for Nanomedicines. Vauthier C, Ponchel G. Springer; Cham, Switzerland 2016. 3.

Google Scholar

121 Truong NP, Whittaker MR, Mak CW, Davis TP. Expert Opin. Drug Delivery. 2015; 12: 129

Google Scholar

122 Andrade F, Videira M, Ferreira D, Sarmento B. Nanomedicine. 2011; 6: 123

Google Scholar

123 Ranjan R, Brittain WJ. Macromolecules. 2007; 40: 6217

Google Scholar

124 Glass EB, Masjedi S, Dudzinski SO, Wilson AJ, Duvall CL, Yull FE, Giorgio TD. ACS Omega. 2019; 4: 16756

Google Scholar

125 Krovi SA, Smith D, Nguyen ST. Chem. Commun. (Cambridge). 2010; 46: 5277

Google Scholar

126 Srinivasan R, Tan LP, Wu H, Yang P.-Y, Kalesh KA, Yao SQ. Org. Biomol. Chem.. 2009; 7: 1821

Google Scholar

127 Hong S, Leroueil PR, Majoros IJ, Orr BG, Baker Jr. JR, Holl MMB. Chem. Biol.. 2007; 14: 107

Google Scholar

128 Patil YB, Toti US, Khdair A, Ma L, Panyam J. Biomaterials. 2009; 30: 859

Google Scholar

129 Cai W, Gao T, Hong H, Sun J. Nanotechnol., Sci. Appl.. 2008; 1: 17

Google Scholar

130 Rosi NL, Giljohann DA, Thaxton CS, Lytton-Jean AK, Han MS, Mirkin CA. Science (Washington, D. C.). 2006; 312: 1027

Google Scholar

131 Aucagne V, Leigh DA. Org. Lett.. 2006; 8: 4505

Google Scholar

132 Tariq M, Ali S, Khalid N. Renewable Sustainable Energy Rev.. 2012; 16: 6303

Google Scholar

133 Steinborn D. Grundlagen der metallorganischen Komplexkatalyse. Springer; Wiesbaden 2007

Google Scholar

134 Copéret C, Chabanas M, Petroff Saint-Arroman R, Basset J.-M. Angew. Chem. Int. Ed.. 2003; 42: 156

Google Scholar

135 Dekker F, Bliek A, Kapteijn F, Moulijn J. Chem. Eng. Sci.. 1995; 50: 3573

Google Scholar

136 Lu Y, Spyra P, Mei Y, Ballauff M, Pich A. Macromol. Chem. Phys.. 2007; 208: 254

Google Scholar

137 Discher BM, Won Y.-Y, Ege DS, Lee JC.-M, Bates FS, Discher DE, Hammer DA. Science (Washington, D. C.). 1999; 284: 1143

Google Scholar

138 Kim KT, Cornelissen JJLM, Nolte RJM, van Hest JCM. Adv. Mater. (Weinheim, Ger.). 2009; 21: 2787

Google Scholar

139 Hickey RJ, Koski J, Meng X, Riggleman RA, Zhang P, Park S.-J. ACS Nano. 2014; 8: 495

Google Scholar

140 Sanka RSP, Balaji K, Leterrier Y, Pandey S, Srivastava M, Srivastava A, Binder WH, Rana S, Michaud V. Chem. Commun. (Cambridge). 2019; 55: 6249

Google Scholar

141 Schüth F. Chem. Unserer Zeit. 2006; 40: 92

Google Scholar

142 van Oers MCM, Abdelmohsen LKEA, Rutjes FPJT, van Hest JCM. Chem. Commun. (Cambridge). 2014; 50: 4040

Google Scholar

143 Ghosh AK, Mathivanan P, Cappiello J. Tetrahedron: Asymmetry. 1998; 9: 1

Google Scholar

144 Desimoni G, Faita G, Jørgensen KA. Chem. Rev.. 2006; 106: 3561

Google Scholar

145 Hargaden GC, Guiry PJ. Chem. Rev.. 2009; 109: 2505

Google Scholar

146 van Oers MCM, Veldmate WS, van Hest JCM, Rutjes FPJT. Polym. Chem.. 2015; 6: 5358

Google Scholar

147 Müller D, Umbricht G, Weber B, Pfaltz A. Helv. Chim. Acta. 1991; 74: 232

Google Scholar

148 Sun X.-L, Stabler CL, Cazalis CS, Chaikof EL. Bioconjugate Chem.. 2006; 17: 52

Google Scholar

149 Lowenthal RE, Masamune S. Tetrahedron Lett.. 1991; 32: 7373

Google Scholar

150 Evans DA, Woerpel KA, Scott MJ. Angew. Chem. Int. Ed. Engl.. 1992; 31: 430

Google Scholar

151 Arnold RM, Huddleston NE, Locklin J. J. Mater. Chem.. 2012; 22: 19357

Google Scholar

152 Pellissier H. Tetrahedron. 2008; 64: 7041

Google Scholar

153 Mase N, Nakai Y, Ohara N, Yoda H, Takabe K, Tanaka F, Barbas CF. J. Am. Chem. Soc.. 2006; 128: 734

Google Scholar

154 Sanson C, Schatz C, Le Meins J.-F, Brûlet A, Soum A, Lecommandoux S. Langmuir. 2010; 26: 2751

Google Scholar

155 Pauloehrl T, Delaittre G, Winkler V, Welle A, Bruns M, Börner HG, Greiner AM, Bastmeyer M, Barner-Kowollik C. Angew. Chem. Int. Ed.. 2012; 51: 1071

Google Scholar

156 Acik G, Cansoy CE, Tasdelen MA. J. Appl. Polym. Sci.. 2019; 136: 47072

Google Scholar

157 Moini N, Zohuriaan-Mehr M, Kabiri K, Khonakdar H. Appl. Surf. Sci.. 2019; 487: 1131

Google Scholar