Preparation of MIP grafts for quercetin by tandem aryl diazonium surface chemistry and photopolymerization

Microchimica Acta

Volumn 180, Issue 15-16, 2013, Pages 1411-1419

  Salmi, Zakaria ^a   Benmehdi, Houcine ^a   Lamouri, Aazdine ^a   Decorse, Philippe ^a   Jouini, Mohamed ^a   Yagci, Yusuf ^b   Chehimi, Mohamed M ^a  

^a UNIVERSITÉ PARIS DIDEROT   (France)

^b ISTANBUL TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Diazonium salts; Photopolymerization; Quercetin; Radical scavenger; Square wave voltammetry; Ultrathin MIP grafts

Indexed keywords

EID: 84888011938     PISSN: 00263672     EISSN: 14365073     Source Type: Journal    
DOI: 10.1007/s00604-013-0993-8     Document Type: Review

References (41)

1. Chehimi MM (2012) Aryl Diazonium Salts: New Coupling Agents in Polymer and Surface Science, (Ed.), ©. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany. ISBN 978-3-527-32998-4.
2. Pinson J, Podvorica F (2005) Attachment of organic layers to conductive or semiconductive surfaces by reduction of diazonium salts. Chem Soc Rev 34: 429.
3. Bélanger D, Pinson J (2011) Electrografting: a powerful method for surface modification. Chem Soc Rev 40: 3995.
4. Jiang DE, Sumpter BG, Dai S (2006) Structure and bonding between an aryl group and metal surfaces. J Am Chem Soc 128: 6030.
5. Jiang DE, Sumpter BG, Dai S (2006b) How do aryl groups attach to a graphene sheet. The Journal of Physical Chemistry B 110: 23628.
6. Mahouche-Chergui S, Gam-Derouich S, Mangeney C, Chehimi MM (2011) Aryl diazonium salts: a new class of coupling agents for bonding polymers, biomacromolecules and nanoparticles to surfaces. Chem Soc Rev 40: 4143.
7. Salmi Z, Gam-Derouich S, Mahouche-Chergui S, Turmine M, Chehimi MM (2012) On the interfacial chemistry of aryl diazonium compounds in polymer science. Chem Pap 66: 369.
8. Gam-Derouich S, Mahouche-Chergui S, Chehimi MM, Ben Romdhane H (2012) Polymer grafting to aryl diazonium-modified materials: methods and applications. In: Chehimi MM (ed) Aryl Diazonium Salts: New Coupling Agents in Polymer and Surface Science. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany.
9. Matrab T, Save M, Charleux B, Pinson J, Cabet-Deliry E, Adenier A, Chehimi MM, Delamar M (2007) Grafting densely-packed poly(n-butyl methacrylate) chains from an iron substrate by aryl diazonium surface-initiated ATRP: XPS monitoring. Surf Sci 601: 2357.
10. Chernyy S, Iruthayaraj J, Ceccato M, Hinge M, Pedersen SU, Daasbjerg K (2012) Elucidation of the mechanism of surface-initiated atom transfer radical polymerization from a diazonium-based initiator layer. J Polym Sci A Polym Chem 50: 4465.
11. Wang GJ, Huang SZ, Wang Y, Liu L, Qiu J, Li Y (2007) Synthesis of water-soluble singlewalled carbon nanotubes by RAFT polymerization. Polymer 48: 728.
12. Tour J M, Hudson J L, Krishnamoorti R, Yurelki K, Mitchell C A (2005) Polymerization initiated at the sidewalls of carbon nanotubes, WO/2005/030858 http://www. wipo. int/pctdb/en/wo. jsp?WO=2005030858.
13. Gam-Derouich S, Carbonnier B, Turmine M, Lang P, Jouini M, Ben Hassen-Chehimi D, Chehimi MM (2010) Electrografted aryl diazonium initiators for surface-confined photopolymerization: a new approach to designing functional polymer coatings. Langmuir 26: 11830.
14. Gam-Derouich S, Mahouche-Chergui S, Turmine M, Piquemal JY, Ben Hassen-Chehimi D, Omastová M, Chehimi MM (2011) A versatile route for surface modification of carbon, metals and semi-conductors by diazonium salt-initiated photopolymerization. Surf Sci 605: 1889.
15. Gam-Derouich S, Lamouri A, Redeuilh C, Decorse P, Maurel F, Carbonnier B, Beyazi{dotless}t S, Yilmaz G, Yagci Y, Chehimi MM (2012) Diazonium salt-derived 4-(dimethylamino)phenyl groups as hydrogen donors in surface-confined radical photopolymerization for bioactive poly(2-hydroxyethyl methacrylate) grafts. Langmuir 28: 8035.
16. Griffete N, Li H, Lamouri A, Redeuilh C, Chen K, Dong CZ, Nowak S, Ammar S, Mangeney C (2012) Magnetic nanocrystals coated by molecularly imprinted polymers for the recognition of bisphenol A. J Mater Chem 22: 1807.
17. Lacroix J C, Ghilane J, Santos L, Trippé-Allard G, Martin P, Randriamahazaka H. Electrografting of conductive oligomers and polymers. In ref. 1, Chap. 8, pp. 181.
18. Blacha A, Koscielniak P, Sitarz M, Szuber J, Zak J (2012) Pedot brushes electrochemically synthesized on thienyl-modified glassy carbon Surfaces. Electrochim Acta 62: 441.
19. Mrabet B, Mejbri A, Mahouche S, Gam-Derouich S, Turmine M, Mechouet M, Lang P, Bakala H, Ladjimi M, Bakhrouf A, Tougaard S, Chehimi MM (2011) Controlled adhesion of Salmonella Typhimurium to poly(oligoethylene glycol methacrylate) grafts. Surface and Interface Analysis 43: 1436.
20. Gehan H, Fillaud L, Chehimi MM, Aubard J, Hohenau A, Felidj N, Mangeney C (2010) Thermo-induced electromagnetic coupling in gold/polymer hybrid plasmonic structures probed by surface-enhanced Raman scattering. ACS Nano 4: 6491.
21. Mahouche Chergui S, Abbas N, Matrab T, Turmine M, Bon Nguyen E, Losno R, Pinson J, Chehimi MM (2010) Uptake of copper ions by carbon fiber/polymer hybrids prepared by tandem diazonium salt chemistry and in situ atom transfer radical polymerization. Carbon 48: 2106.
22. Gam-Derouich S, Nguyen MN, Madani A, Maouche N, Lang P, Perruchot C, Chehimi MM (2010) Aryl diazonium salt surface chemistry and ATRP for the preparation of molecularly imprinted polymer grafts on gold substrates. Surf Interface Anal 42: 1050.
23. Molinelli A, Weiss R, Mizaikoff RB (2002) Advanced solid phase extraction using molecularly imprinted polymers for the determination of quercetin in red wine. J Agric Food Chem 50: 1804.
24. Xie J, Zhu L, Luo H, Zhou L, Li C, Xu X (2001) Direct extraction of specific pharmacophoric flavonoids from gingko leaves using a molecularly imprinted polymer for quercetin. J Chromatogr A 934: 1.
25. Zhu LY, Wang ZH, Chen XY, Zhang FF, Xia YZ, Li YH (2011) Molecularly imprinted polymer incorporated carbon nanotube modified electrode for selective determination of quercetin. J Instrumental Anal 30: 18.
26. Castro López MM, Cela Pérez MC, Dopico-García MS, López Vilariño JM, Gónzalez-Rodríguez MV, Barral Losada LF (2012) Preparation, evaluation and characterization of quercetin-molecularly imprinted polymer for preconcentration and clean-up of catechins. Anal Chim Acta 721: 68.
27. Gnanou Y, Hizal G (2004) Effect of phenol and derivatives on atom transfer radical polymerization in the presence of air. J Polym Sci A Polym Chem 42: 351.
28. Gam-Derouich S, Jouini M, Ben Hassen-Chehimi D, Chehimi MM (2012) Aryl diazonium salt surface chemistry and graft photopolymerization for the preparation of molecularly imprinted polymer biomimetic sensor layers. Electrochim Acta 73: 45.
29. Chehimi, M. M., Gam-Derouich, S., and Madani, A. (2010) PCT/FR2011/051992.
30. Gam-Derouich S, Mahouche-Chergui S, Truong S, Ben Hassen-Chehimi D, Chehimi MM (2011) Design of molecularly imprinted polymer grafts with embedded gold nanoparticles through the interfacial chemistry of aryl diazonium salts. Polymer 52: 4463.
31. Khlifi A, Gam-Derouich S, Jouini M, Kalfat R, Chehimi MM (2013) Melamine-imprinted polymer grafts through surface photopolymerisation initiated by aryl layers from diazonium salts. Food Control 31: 379.
32. Mauguière-Guyonnet F, Burgetm D, Fouassier JP (2007) The role of the photoinitiating systems towards the inhibiting effect of phenolic compounds in the photopolymerization of acrylates. Prog Org Coat 59: 37.
33. Cokbaglan L, Arsu N, Yagci Y (2003) 2-mercaptothioxanthone as a novel photoinitiator for free radical polymerization. Macromolecules 36: 2649.
34. Yagci Y, Jockusch S, Turro NJ (2010) Photoinitiated polymerization: advances, challenges, and opportunities. Macromolecules 43: 6245.
35. Furniss S, Hannaford AJ, Smith PWG, Tatchell AR (1989) Vogel's Textbook of Practical Organic Chemistry, 5th edn. Longman, London, 920.
36. Adenier A, Bernard MC, Chehimi MM, Cabet-Deliry E, Desbat B, Fagebaume O, Pinson J, Podvorica F (2001) Covalent modification of iron surfaces by electrochemical reduction of aryldiazonium salts. J Am Chem Soc 123: 4541.
37. Lin S, Lin C-W, Jhang J-H, Hung W-H (2012) Electrodeposition of long-chain alkylaryl layers on Au surfaces. J Phys Chem C 116: 17048.
38. Bouktit B, Salmi Z, Decorse P, Lecocq H, Jouini M, Aswal D, Singh A, Chehimi MM (2013), Polypyrrole/Ag nanocomposite films on diazonium salt modified indium tin oxide substrate, J Colloid Sci Biotechnol, in press.
39. Tasdelen MA, Kiskan B, Yagci Y (2006) Photoinitiated free radical polymerization using benzoxazines as hydrogen donors. Macromol Rapid Commun 27: 1539.
40. Hertog MGL, Hollman PCH, van de Putte B (1993) Content of potentially anticarcinogenic flavonoids of tea infusions, wines, and fruit juices. J Agrlc Food Chem 41: 1242.
41. Ivana N, Marijan S, Sebojka KL (2010) Characterisation of catechins in green and black teas using square-wave voltammetry and RP-HPLC-ECD. Food Chem 122: 1283.