journal article·2018-10

Preparation of light-sensitive polymer/graphene composite via molecular recognition by β-cyclodextrin

Shuai He, Hui Li, Hualin Chen

Journal of Materials Science· Volume 53· Issue 20
Publisher page

Abstract

The dispersion of graphene in water has generally been considered an insurmountable challenge owing to its hydrophobic nature. In this study, a new type of light-sensitive polymer/graphene composite (AzoPEO/β-CD–RGO) was synthesized by the reversible host–guest interaction between azobenzene-terminal poly(ethylene oxide) (AzoPEO) and a β-cyclodextrin (β-CD) host attached to the surface of graphene via hydrogen bonding. In water, the AzoPEO/β-CD–RGO composite not only is well dispersed, but also exhibits reversible dispersion/aggregation behavior triggered by UV and visible light. Moreover, the graphene composite can be used to fabricate a light-responsive graphene-based drug delivery system. This kind of light-responsive graphene composite, which efficiently allows the control of graphene dispersion/aggregation, may find wide applications in the preparation of intelligent drug delivery systems, smart sensors, and switching devices.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Graphene and Nanomaterials Applications · Graphene research and applications · Advanced Sensor and Energy Harvesting Materials

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (66)

Show source-provided references
1. Ramirez S, Chan K, Hernandez R et al (2017) Thermal and magnetic properties of nanostructured densified ferrimagnetic composites with graphene–graphite fillers. Mater Des 118:75–8010.1016/j.matdes.2017.01.018 ↗
2. Eksik O, Bartolucci SF, Gupta T, Fard H, Borca-Tasciuc T, Koratkar N (2016) A novel approach to enhance the thermal conductivity of epoxy nanocomposites using graphene core–shell additives. Carbon 101:239–24410.1016/j.carbon.2016.01.095 ↗
3. Tai Z, Yang J, Qi Y, Yan X, Xue Q (2013) Synthesis of a graphene oxide–polyacrylic acid nanocomposite hydrogel and its swelling and electroresponsive properties. RSC Adv 3:12751–1275710.1039/c3ra22335c ↗
4. Ferrari AC, Basko DM (2013) Raman spectroscopy as a versatile tool for studying the properties of graphene. Nat Nanotechnol 8:235–24610.1038/nnano.2013.46 ↗
5. Zang J, Ryu S, Pugno N et al (2013) Multifunctionality and control of the crumpling and unfolding of large-area graphene. Nat Mater 12:321–32510.1038/nmat3542 ↗
6. Mahakul PC, Sa K, Das B et al (2017) Preparation and characterization of PEDOT:PSS/reduced graphene oxide-carbon nanotubes hybrid composites for transparent electrode applications. J Mater Sci 52:5696–570710.1007/s10853-017-0806-2 ↗
7. Olowojoba GB, Kopsidas S, Eslava S et al (2017) A facile way to produce epoxy nanocomposites having excellent thermal conductivity with low contents of reduced graphene oxide. J Mater Sci 52:7323–734410.1007/s10853-017-0969-x ↗
8. Gorbachev R, Song J, Yu G et al (2014) Detecting topological currents in graphene superlattices. Science 346:448–45110.1126/science.1254966 ↗
9. Li W, Geng X, Guo Y et al (2011) Reduced graphene oxide electrically contacted graphene sensor for highly sensitive nitric oxide detection. ACS Nano 5:6955–696110.1021/nn201433r ↗
10. Li X, Zhu Y, Cai W et al (2009) Transfer of large-area graphene films for high-performance transparent conductive electrodes. Nano Lett 9:4359–436310.1021/nl902623y ↗
11. Wei D, Astley MR, Harris N, White R, Ryhänen T, Kivioja J (2014) Graphene nanoarchitecture in batteries. Nanoscale 6:9536–954010.1039/C4NR02089H ↗
12. Machado BF, Serp P (2012) Graphene-based materials for catalysis. Catal Sci Technol 2:54–7510.1039/C1CY00361E ↗
13. Guo R, Jiao T, Li R et al (2017) Sandwiched Fe3O4/carboxylate graphene oxide nanostructures constructed by layer-by-layer assembly for highly efficient and magnetically recyclable dye removal. ACS Sustain Chem Eng 6:1279–128810.1021/acssuschemeng.7b03635 ↗
14. Luo X, Ma K, Jiao T et al (2017) Graphene oxide-polymer composite Langmuir films constructed by interfacial thiol–ene photopolymerization. Nanoscale Res Lett 12:9910.1186/s11671-017-1864-8 ↗
15. Liu Y, Hou C, Jiao T et al (2018) Self-assembled AgNP-containing nanocomposites constructed by electrospinning as efficient dye photocatalyst materials for wastewater treatment. Nanomaterials 8:3510.3390/nano8010035 ↗
16. Zhou J, Liu Y, Jiao T et al (2018) Preparation and enhanced structural integrity of electrospun poly(ε-caprolactone)-based fibers by freezing amorphous chains through thiol–ene click reaction. Colloid Surf A 538:7–1310.1016/j.colsurfa.2017.10.077 ↗
17. Gao Y, Jiao T, Ma K et al (2017) Variable self-assembly and in situ host–guest reaction of beta-cyclodextrin-modified graphene oxide composite Langmuir films with azobenzene compounds. RSC Adv 7:41043–4105110.1039/C7RA07109D ↗
18. Tran MH, Jeong HK (2018) Improved dispersion of graphite derivatives by solution plasma. J Mater Sci 53:3388–339710.1007/s10853-017-1799-6 ↗
19. He H, Gao C (2010) General approach to individually dispersed, highly soluble, and conductive graphene nanosheets functionalized by nitrene chemistry. Chem Mater 22:5054–506410.1021/cm101634k ↗
20. Liang Y, Wu D, Feng X, Müllen K (2009) Dispersion of graphene sheets in organic solvent supported by ionic interactions. Adv Mater 21:1679–168310.1002/adma.200803160 ↗
21. Su Q, Pang S, Alijani V, Li C, Feng X, Müllen K (2009) Composites of graphene with large aromatic molecules. Adv Mater 21:3191–319510.1002/adma.200803808 ↗
22. Markovic ZM, Harhaji LM, Todorovic BM et al (2011) In vitro comparison of the photothermal anticancer activity of graphene nanoparticles and carbon nanotubes. Biomaterials 32:1121–112910.1016/j.biomaterials.2010.10.030 ↗
23. Lv W, Guo M, Liang M et al (2010) Graphene-DNA hybrids: self-assembly and electrochemical detection performance. J Mater Chem 20:6668–667310.1039/c0jm01066a ↗
24. Bai H, Xu Y, Zhao L, Li C, Shi G (2009) Non-covalent functionalization of graphene sheets by sulfonated polyaniline. Chem Commun 13:1667–166910.1039/b821805f ↗
25. Georgakilas V, Otyepka M, Bourlinos AB et al (2012) Functionalization of graphene: covalent and non-covalent approaches, derivatives and applications. Chem Rev 112:6156–621410.1021/cr3000412 ↗
26. He S, Qu M, Feng Y (2015) Gas-induced reversible dispersion/aggregation of graphene. Chemnanomat 1:438–444
27. Li Z, Zhang W, Li Y, Wang H, Qin Z (2018) Activated pyrene decorated graphene with enhanced performance for electrochemical energy storage. Chem Eng J 334:845–85410.1016/j.cej.2017.10.023 ↗
28. Jiang D, Zhu H, Yang W, Cui L, Liu J (2017) One-side non-covalent modification of CVD graphene sheet using pyrene-terminated PNIPAAm generated via RAFT polymerization for the fabrication of thermo-responsive actuators. Sensor Actuat B 239:193–20210.1016/j.snb.2016.08.006 ↗
29. Li Y, Chen Y, Deng D, Luo L, He H, Wang Z (2017) Water-dispersible graphene/amphiphilic pyrene derivative nanocomposite: high AuNPs loading capacity for CEA electrochemical immunosensing. Sensor Actuat B 248:966–97210.1016/j.snb.2017.02.138 ↗
30. Boström CE, Gerde P, Hanberg A et al (2002) Cancer risk assessment, indicators, and guidelines for polycyclic aromatic hydrocarbons in the ambient air. Environ Health Persp 110:451–48810.1289/ehp.02110s3451 ↗
31. Guo Y, Guo S, Ren J, Zhai Y, Dong S, Wang E (2010) Cyclodextrin functionalized graphene nanosheets with high supramolecular recognition capability: synthesis and host–guest inclusion for enhanced electrochemical performance. ACS Nano 4:4001–401010.1021/nn100939n ↗
32. Liu J, Yang W, Tao L, Li D, Boyer C, Davis TP (2010) Thermosensitive graphene nanocomposites formed using pyrene-terminal polymers made by RAFT polymerization. J Polym Sci Pol Chem 48:425–43310.1002/pola.23802 ↗
33. Fang M, Long J, Zhao W, Wang L, Chen G (2010) pH-responsive chitosan-mediated graphene dispersions. Langmuir 26:16771–1677410.1021/la102703b ↗
34. Roy D, Cambre JN, Sumerlin BS (2010) Future perspectives and recent advances in stimuli-responsive materials. Prog Polym Sci 35:278–30110.1016/j.progpolymsci.2009.10.008 ↗
35. Yamaguchi H, Kobayashi Y, Kobayashi R, Takashima Y, Hashidzume A, Harada A (2012) Photoswitchable gel assembly based on molecular recognition. Nat Commun 3:60310.1038/ncomms1617 ↗
36. Sahu A, Choi WI, Tae G (2012) A stimuli-sensitive injectable graphene oxide composite hydrogel. Chem Commun 48:5820–582210.1039/c2cc31862h ↗
37. Lo CW, Zhu DF, Jiang HR (2011) An infrared-light responsive graphene–oxide incorporated poly(N-isopropylacrylamide) hydrogel nanocomposite. Soft Matter 7:5604–560910.1039/c1sm00011j ↗
38. Cai Y, Zhang A, Feng YP, Zhang C (2011) Switching and rectification of a single light-sensitive diarylethene molecule sandwiched between graphene nanoribbons. J Chem Phys 135:1847031–1847036
39. Wang D, Ye G, Wang X, Wang X (2011) Graphene functionalized with azo polymer brushes: surface-initiated polymerization and photoresponsive properties. Adv Mater 23:1122–112510.1002/adma.201003653 ↗
40. Chen J, Yao B, Li C, Shi G (2013) An improved Hummers method for eco-friendly synthesis of graphene oxide. Carbon 64:225–22910.1016/j.carbon.2013.07.055 ↗
41. Guo Z, Feng Y, Zhu D et al (2013) Light-switchable single-walled carbon nanotubes based on host–guest chemistry. Adv Funct Mater 23:5010–501810.1002/adfm.201300434 ↗
42. Zhu Y, Murali S, Cai W et al (2010) Graphene and graphene oxide: synthesis, properties, and applications. Adv Mater 22:3906–392410.1002/adma.201001068 ↗
43. Shen X, Lin X, Yousefi N, Jia J, Kim J (2014) Wrinkling in graphene sheets and graphene oxide papers. Carbon 66:84–9210.1016/j.carbon.2013.08.046 ↗
44. Stobinski L, Lesiak B, Malolepszy A et al (2014) Graphene oxide and reduced graphene oxide studied by the XRD, TEM and electron spectroscopy methods. J Electron Spectrosc 195:145–15410.1016/j.elspec.2014.07.003 ↗
45. Steiner T, Koellner G (1994) Crystalline beta-Cyclodextrin hydrate at various humidities: fast, continuous, and reversible dehydration studied by X-ray diffraction. J Am Chem Soc 116:5122–512810.1021/ja00091a014 ↗
46. Wang J, Cao Y, Sun B, Wang C (2011) Physicochemical and release characterisation of garlic oil-β-cyclodextrin inclusion complexes. Food Chem 127:1680–168510.1016/j.foodchem.2011.02.036 ↗
47. Xu Y, Bai H, Lu G, Li C, Shi G (2008) Flexible graphene films via the filtration of water-soluble noncovalent functionalized graphene sheets. J Am Chem Soc 130:5856–585710.1021/ja800745y ↗
48. Li D, Müller MB, Gilje S, Kaner RB, Wallace GG (2008) Processable aqueous dispersions of graphene nanosheets. Nat Nanotechnol 3:101–10510.1038/nnano.2007.451 ↗
49. Zhao H, Ji X, Wang B et al (2015) An ultra-sensitive acetylcholinesterase biosensor based on reduced graphene oxide-Au nanoparticles-β-cyclodextrin/Prussian blue–chitosan nanocomposites for organophosphorus pesticides detection. Biosens Bioelectron 65:23–3010.1016/j.bios.2014.10.007 ↗
50. Scatena LF, Brown MG, Richmond GL (2001) Water at hydrophobic surfaces: weak hydrogen bonding and strong orientation effects. Science 292:908–91210.1126/science.1059514 ↗
51. Ang PK, Wang S, Bao Q, Thong JT, Loh KP (2009) High-throughput synthesis of graphene by intercalation-exfoliation of graphite oxide and study of ionic screening in graphene transistor. ACS Nano 3:3587–359410.1021/nn901111s ↗
52. Marcano DC, Kosynkin DV, Berlin JM et al (2010) Improved synthesis of graphene oxide. ACS Nano 4:4806–481410.1021/nn1006368 ↗
53. Benedict TJ, Banumathi S, Veluchamy A, Gangadharan R, Ahamad AZ, Rajendran S (1998) Characterization of plasticized solid polymer electrolyte by XRD and AC impedance methods. J Power Sources 75:171–17410.1016/S0378-7753(98)00063-9 ↗
54. Park S, An J, Jung I et al (2009) Colloidal suspensions of highly reduced graphene oxide in a wide variety of organic solvents. Nano Lett 9:1593–159710.1021/nl803798y ↗
55. Fang M, Wang K, Lu H, Yang Y, Nutt S (2009) Covalent polymer functionalization of graphene nanosheets and mechanical properties of composites. J Mater Chem 19:7098–710510.1039/b908220d ↗
56. Wang G, Shen X, Yao J, Park J (2009) Graphene nanosheets for enhanced lithium storage in lithium ion batteries. Carbon 47:2049–205310.1016/j.carbon.2009.03.053 ↗
57. Zhang J, Yang H, Shen G, Cheng P, Zhang J, Guo S (2010) Reduction of graphene oxide vial-ascorbic acid. Chem Commun 46:1112–111410.1039/B917705A ↗
58. Shanmugam M, Ramesh D, Nagalakshmi V, Kavitha R, Rajamohan R, Stalin T (2008) Host–guest interaction of l-tyrosine with β-cyclodextrin. Spectrochim Acta A 71:125–13210.1016/j.saa.2007.10.054 ↗
59. Wagner BD (2012) Hydrogen bonding of excited states in supramolecular host–guest inclusion complexes. Phys Chem Chem Phys 14:8825–883510.1039/c2cp40310b ↗
60. Zhu X, Xu S (2010) Determination of l-tyrosine by β-cyclodextrin sensitized fluorescence quenching method. Spectrochim Acta A 77:566–57110.1016/j.saa.2010.04.028 ↗
61. Han Y, Shen M, Wu Y et al (2013) Preparation and electrochemical performances of PEDOT/sulfonic acid-functionalized graphene composite hydrogel. Synthetic Met 172:21–2710.1016/j.synthmet.2013.04.001 ↗
62. Yang X, Zhang X, Liu Z, Ma Y, Huang Y, Chen Y (2008) High-efficiency loading and controlled release of doxorubicin hydrochloride on graphene oxide. J Phys Chem C 112:17554–1755810.1021/jp806751k ↗
63. Liu J, Cui L, Losic D (2013) Graphene and graphene oxide as new nanocarriers for drug delivery applications. Acta Biomater 9:9243–925710.1016/j.actbio.2013.08.016 ↗
64. Goenka S, Sant V, Sant S (2014) Graphene-based nanomaterials for drug delivery and tissue engineering. J Control Release 173:75–8810.1016/j.jconrel.2013.10.017 ↗
65. Zhou K, Zhu Y, Yang X, Li C (2010) One-pot preparation of graphene/Fe3O4 composites by a solvothermal reaction. New J Chem 34:2950–295510.1039/c0nj00283f ↗
66. Zheng XT, Ma XQ, Li CM (2016) Highly efficient nuclear delivery of anti-cancer drugs using a bio-functionalized reduced graphene oxide. J Colloid Interf Sci 467:35–4210.1016/j.jcis.2015.12.052 ↗