Thermotriggered Catalyst-Free Modification of a Glass Surface with an Orthogonal Agent Possessing Nitrile N-Oxide and Masked Ketene Functions

Langmuir

Volumn 32, Issue 1, 2016, Pages 309-315

  Cheawchan, Sumitra ^a   Uchida, Satoshi ^a   Sogawa, Hiromitsu ^a   Koyama, Yasuhito ^b   Takata, Toshikazu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CYANIDES; DECOMPOSITION; GLASS; MASS SPECTROMETRY; NUCLEOPHILES; ORGANIC POLYMERS; SECONDARY ION MASS SPECTROMETRY; SURFACE TREATMENT; X RAY PHOTOELECTRON SPECTROSCOPY;

1 ,3-DIPOLARCYCLOADDITION; FUNCTIONALIZED SURFACES; MODIFIED SURFACES; SILICA NANOPARTICLES; SURFACE CHARACTERISTICS; TIME OF FLIGHT SECONDARY ION MASS SPECTROMETRY; UNSATURATED BONDS; WATER CONTACT ANGLE;

ORTHOGONAL FUNCTIONS;

EID: 84954217407     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/acs.langmuir.5b03881     Document Type: Article

References (46)

1. Goddard, J. M.; Hotchkiss, J. H. Polymer surface modification for the attachment of bioactive compounds Prog. Polym. Sci. 2007, 32, 698-725 10.1016/j.progpolymsci.2007.04.002
2. Desmet, T.; Morent, R.; Geyter, N. D.; Leys, C.; Schacht, E.; Dubruel, P. Nonthermal plasma technology as a versatile strategy for polymeric biomaterials surface modification: a review Biomacromolecules 2009, 10, 2351-2378 10.1021/bm900186s
3. Kango, S.; Kalia, S.; Celli, A.; Njuguna, J.; Habibi, Y.; Kumar, R. Surface modification of inorganic nanoparticles for development of organic-inorganic nanocomposites-A review Prog. Polym. Sci. 2013, 38, 1232-1261 10.1016/j.progpolymsci.2013.02.003
4. Ulman, A. Formation and structure of self-assembled monolayers Chem. Rev. 1996, 96, 1533-1554 10.1021/cr9502357
5. Ohno, K.; Kayama, Y.; Ladmiral, V.; Fukuda, T.; Tsujii, Y. A versatile method of initiator fixation for surface-initiated living radical polymerization on polymeric substrates Macromolecules 2010, 43, 5569-5574 10.1021/ma1008258
6. Moraes, J.; Ohno, K.; Maschmeyer, T.; Perrier, S. Synthesis of silica-polymer core-shell nanoparticles by reversible addition-fragmentation chain transfer polymerization Chem. Commun. 2013, 49, 9077-9088 10.1039/c3cc45319g
7. Huang, Y.; Morinaga, T.; Tai, Y.; Tsujii, Y.; Ohno, K. Immobilization of semisoft colloidal crystals formed by polymer-brush-afforded hybrid particles Langmuir 2014, 30, 7304-7312 10.1021/la5011488
8. Moses, J. E.; Moorhouse, A. D. The growing applications of click chemistry Chem. Soc. Rev. 2007, 36, 1249-1262 10.1039/b613014n
9. Gouget-Laemmel, A. C.; Yang, J.; Lodhi, M. A.; Siriwardena, A.; Aureau, D.; Boukherroub, R.; Chazalviel, J. N.; Ozanam, F.; Szunerits, S. Functionalization of azide-terminated silicon surfaces with glycans using click chemistry: XPS and FTIR study J. Phys. Chem. C 2013, 117, 368-375 10.1021/jp309866d
10. Hoyle, C. E.; Bowman, C. N. Thiol-ene click chemistry Angew. Chem., Int. Ed. 2010, 49, 1540-1573 10.1002/anie.200903924
11. Lowe, A. B. Thiol-ene "click" reactions and recent applications in polymer and materials synthesis Polym. Chem. 2010, 1, 17-36 10.1039/B9PY00216B
12. Wasserman, S. R.; Tao, Y. T.; Whitesides, G. M. Structure and reactivity of alkylsiloxane monolayers formed by reaction of alkyltrichlorosilanes on silicon substrates Langmuir 1989, 5, 1074-1087 10.1021/la00088a035
13. Haensch, C.; Hoeppener, S.; Schubert, U. S. Chemical modification of self-assembled silane based monolayers by surface reactions Chem. Soc. Rev. 2010, 39, 2323-2334 10.1039/b920491a
14. Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Self-assembled monolayers of thiolates on metals as a form of nanotechnology Chem. Rev. 2005, 105, 1103-1169 10.1021/cr0300789
15. Heaney, F. Nitrile oxide/alkyne cycloadditions-A credible platform for synthesis of bioinspired molecules by metal-free molecular clicking Eur. J. Org. Chem. 2012, 2012, 3043-3058 10.1002/ejoc.201101823
16. Sudo, A.; Uchino, S.; Endo, T. Development of a living anionic polymerization of ethylphenylketene: A novel approach to well-defined polyester synthesis Macromolecules 1999, 32, 1711-1713 10.1021/ma981567r
17. Sudo, A.; Uchino, S.; Endo, T. Application of ketenes to well-defined polyester synthesis. III. Living anionic polymerization of ethyl(4-methoxyphenyl)ketene-development of polyester having masked phenol side chain J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 1596-1600 10.1002/pola.1136
18. Nagai, D.; Sudo, A.; Endo, T. Anionic alternating copolymerization of ketene and aldehyde: control of enantioselectivity by bisoxazoline-type ligand for synthesis of optically active polyesters Macromolecules 2006, 39, 8898-8900 10.1021/ma0620971
19. Ogoshi, T.; Shiga, R.; Hashizume, M.; Yamagishia, T.-A. Clickable" pillar[5]arenes Chem. Commun. 2011, 47, 6927-6929 10.1039/c1cc11864a
20. Ogoshi, T.; Yamafuji, D.; Kotera, D.; Aoki, T.; Fujinami, S.; Yamagishi, T.-A. Clickable di- and tetrafunctionalized pillar[n]arenes (n = 5, 6) by oxidation-reduction of pillar[n]arene units J. Org. Chem. 2012, 77, 11146-11152 10.1021/jo302283n
21. Ogoshi, T.; Iizuka, R.; Kotera, D.; Yamagishi, T.-A. Synthesis of a pillar[5]arene-based [2]rotaxane with two equivalent stations via copper(I)-catalyzed alkyne-azide cycloaddition Org. Lett. 2015, 17, 350-353 10.1021/ol5034699
22. Kircher, L.; Theato, P.; Cameron, N. R. Reactive thiol-ene emulsion-templated porous polymers incorporating pentafluorophenyl acrylate Polymer 2013, 54, 1755-1761 10.1016/j.polymer.2013.01.024
23. Thielke, M. W.; Bruckner, E. P.; Wong, D. L.; Theato, P. Thiol-ene modification of electrospun polybutadiene fibers crosslinked by UV irradiation Polymer 2014, 55, 5596-5599 10.1016/j.polymer.2014.09.002
24. He, L.; Szopinski, D.; Wu, Y.; Luinstra, G. A.; Theato, P. Toward self-healing hydrogels using one-pot thiol-ene click and borax-diol chemistry ACS Macro Lett. 2015, 4, 673-678 10.1021/acsmacrolett.5b00336
25. Huisgen, R. 1,3-Dipolar cycloadditions. Past and future Angew. Chem., Int. Ed. Engl. 1963, 2, 565-598 10.1002/anie.196305651
26. Mukaiyama, T.; Hoshino, T. The reactions of primary nitroparaffins with isocyanates J. Am. Chem. Soc. 1960, 82, 5339-5342 10.1021/ja01505a017
27. Shimizu, T.; Hayashi, Y.; Shibafuchi, H.; Teramura, K. A convenient preparative method of nitrile oxides by the dehydration of primary nitrocompounds with ethyl chloroformate or benzenesulfonyl chloride in the presence of triethylamine Bull. Chem. Soc. Jpn. 1986, 59, 2827-2831 10.1246/bcsj.59.2827
28. Moriya, O.; Nakamura, H.; Kageyama, T.; Urata, Y. Synthesis of isoxazolines and isoxazoles from aldoximes by the use of sodium bromite with organotin halide Tetrahedron Lett. 1989, 30, 3987-3990 10.1016/S0040-4039(00)99302-X
29. Koyama, Y.; Yonekawa, M.; Takata, T. New Click chemistry: Click polymerization via 1,3-dipolar addition of homo-ditopic aromatic nitrile oxides formed in situ Chem. Lett. 2008, 37, 918-919 10.1246/cl.2008.918
30. Lee, Y. G.; Koyama, Y.; Yonekawa, M.; Takata, T. New Click chemistry: Polymerization based on 1,3-dipolar cycloaddition of a homo ditopic nitrile N-oxide and transformation of the resulting polymers into reactive polymers Macromolecules 2009, 42, 7709-7717 10.1021/ma9014577
31. Lee, Y. G.; Koyama, Y.; Yonekawa, M.; Takata, T. Synthesis of main-chain-type polyrotaxanes by new click polymerization using homoditopic nitrile N-oxides via rotaxanation-polymerization protocol Macromolecules 2010, 43, 4070-4080 10.1021/ma100262g
32. Lee, Y. G.; Yonekawa, M.; Koyama, Y.; Takata, T. Synthesis of a kinetically stabilized homoditopic nitrile N-oxide directed toward catalyst-free click polymerization Chem. Lett. 2010, 39, 420-421 10.1246/cl.2010.420
33. Jang, K.; Miura, K.; Koyama, Y.; Takata, T. Catalyst- and solvent-free click synthesis of cyclodextrin-based polyrotaxanes exploiting a nitrile N-oxide Org. Lett. 2012, 14, 3088-3091 10.1021/ol3011024
34. Yonekawa, M.; Koyama, Y.; Kuwata, S.; Takata, T. Intramolecular 1,3-Dipolar cycloaddition of nitrile N-oxide accompanied by dearomatization Org. Lett. 2012, 14, 1164-1167 10.1021/ol300125s
35. Koyama, Y.; Miura, K.; Cheawchan, S.; Seo, A.; Takata, T. Cascade functionalization of unsaturated bond-containing polymers using ambident agents possessing both nitrile N-oxide and electrophilic functions Chem. Commun. 2012, 48, 10304-10306 10.1039/c2cc35158g
36. Cheawchan, S.; Koyama, Y.; Uchida, S.; Takata, T. Catalyst-free click cascade functionalization of unsaturated-bond-containing polymers using masked-ketene-tethering nitrile N-oxide Polymer 2013, 54, 4501-4510 10.1016/j.polymer.2013.06.020
37. Wang, C.-G.; Koyama, Y.; Yonekawa, M.; Uchida, S.; Takata, T. Polymer nitrile N-oxides directed toward catalyst- and solvent-free click grafting Chem. Commun. 2013, 49, 7723-7725 10.1039/c3cc42992j
38. Wang, C.-G.; Koyama, Y.; Uchida, S.; Takata, T. Synthesis of highly reactive polymer nitrile N-oxides for effective solvent-free grafting ACS Macro Lett. 2014, 3, 286-290 10.1021/mz500069f
39. Matsumura, T.; Koyama, Y.; Uchida, S.; Yonekawa, M.; Yui, T.; Ishitani, O.; Takata, T. Fluorescent poly(boron enaminoketonate)s: synthesis via the direct modification of polyisoxazoles obtained from the click polymerization of a homoditopic nitrile N-oxide and diynes Polym. J. 2014, 46, 609-616 10.1038/pj.2014.31
40. Kumbaraci, V.; Talinli, N.; Yaʇci, Y. Photoinduced crosslinking of polymers containing pendant hydroxyl groups by using bisbenzodioxinones Macromol. Rapid Commun. 2007, 28, 72-77 10.1002/marc.200600653
41. Tasdelen, M. A.; Kumbaraci, V.; Talinli, N.; Yaʇci, Y. Photoinduced cross-linking polymerization of monofunctional vinyl monomer without conventional photoinitiator and cross-linker Macromolecules 2007, 40, 4406-4408 10.1021/ma0709811
42. Durmaz, Y. Y.; Kumbaraci, V.; Demirel, A. L.; Talinli, N.; Yaʇci, Y. Graft copolymers by the combination of ATRP and photochemical acylation process by using benzodioxinones Macromolecules 2009, 42, 3743-3749 10.1021/ma900360s
43. Leibfarth, F. A.; Schneider, Y.; Lynd, N. A.; Schultz, A.; Moon, B.; Kramer, E. J.; Bazan, G. C.; Hawker, C. J. Ketene functionalized polyethylene: Control of cross-link density and material properties J. Am. Chem. Soc. 2010, 132, 14706-14709 10.1021/ja1060643
44. Leibfarth, F. A.; Kang, M.; Ham, M.; Kim, J.; Campos, L. M.; Gupta, N.; Moon, B.; Hawker, C. A facile route to ketene-functionalized polymers for general materials applications Nat. Chem. 2010, 2, 207-212 10.1038/nchem.538
45. Jung, H.; Leibfarth, F. A.; Woo, S.; Lee, S.; Kang, M.; Moon, B.; Hawker, C. J.; Bang, J. Efficient surface neutralization and enhanced substrate adhesion through ketene mediated crosslinking and functionalization Adv. Funct. Mater. 2013, 23, 1597-1602 10.1002/adfm.201201352
46. Klajn, R. Spiropyran-based dynamic materials Chem. Soc. Rev. 2014, 43, 148-184 10.1039/C3CS60181A