Back
 MSA  Vol.9 No.12 , November 2018
Enhanced Nonlinear Absorption Performance of Reduced Graphene Oxide Nanohybrid Covalently Functionalized by Porphyrin via 1,3-Dipolar Cycloaddition
Abstract: Porphyrin-functionalized reduced graphene oxide (RGO-TPP) was prepared by 1,3-dipolar cycloaddition reaction and characterized by Fourier transform infrared spectroscopy, Raman, ultraviolet/visible absorption, fluorescence, and transmission electron microscopy. At the same level of linear transmittance, RGO-TPP exhibited more enhanced optical nonlinearities than RGO and the pristineporphyrin, implying a remarkable accumulation effect as a result of the covalent link between RGO and porphyrin. The role of energy/electron transfer in the optical nonlinearities of RGO-TPP was investigated by fluorescence and Raman spectroscopy. All the results displayed that RGO can be covalently functionalized with porphyrins by the proposed approach.
Cite this paper: Zhang, N. and Cong, X. (2018) Enhanced Nonlinear Absorption Performance of Reduced Graphene Oxide Nanohybrid Covalently Functionalized by Porphyrin via 1,3-Dipolar Cycloaddition. Materials Sciences and Applications, 9, 972-984. doi: 10.4236/msa.2018.912070.
References

[1]   Li, Y., Zhang, W., Guo, B. and Datta, D. (2017) Interlayer Shear of Nanomaterials: Graphene-Graphene, Boron Nitride-Boron Nitride and Graphene-Boron Nitride. Acta Mechanica Solida Sinica, 30, 234-240.
https://doi.org/10.1016/j.camss.2017.05.002

[2]   Navarro, J.J., Calleja, F., Miranda, R., et al. (2017) High Yielding and Extremely Site-Selective Covalent Functionalization of Graphene. Chemical Communications, 53, 10418-10421.
https://doi.org/10.1039/C7CC04458E

[3]   Geim, A.K. and Novoselov, K.S. (2007) The Rise of Graphene. Nature Materials, 6, 183-191.
https://doi.org/10.1038/nmat1849

[4]   Mao, S., Chang, J., Pu, H., et al. (2017) Two-Dimensional Nanomaterial-Based Field-Effect Transistors for Chemical and Biological Sensing. Chemical Society Reviews, 46, 6872-6904.
https://doi.org/10.1039/C6CS00827E

[5]   Xu, X., Chen, J., Luo, X., Lu, J., Zhou, H., Wu, W., Zhan, H., Dong, Y., Yan, S., Qin, J. and Li, Z. (2012) Poly(9,9’-Diheylfluorenecarbozole) Functionalized with Reduced Graphene Oxide: Convenient Synthesis Using Nitrogen-Based Nucleophiles and Potential Applications in Optical Limiting. Chemistry—A European Journal, 18, 14384-14391.
https://doi.org/10.1002/chem.201201360

[6]   Stankovich, S., Dikin, D.A., Dommett, G.H.B., Kohlhaas, K.M., Zimney, E.J., Stach, E.A., Piner, R.D., Nguyen, S.T. and Ruoff, R.S. (2004) Graphene-Based Composite Materials. Nature, 442,282-286.
https://doi.org/10.1038/nature04969

[7]   Zheng, C., Huang, L., Guo, Q.H., Chen, W.Z. and Li, W. (2018) Nonlinear Optical Responses of Carbon Quantum Dots Anchored on Graphene Oxide Hybrid in Solid-State Transparent Monolithic Silica Gel Glasses. Optics and Laser Technology, 107, 281-290.
https://doi.org/10.1016/j.optlastec.2018.06.013

[8]   Singla, S., Animdanso, E., Islam, A.E., Ngo, Y., Kim, S.S., Naik, R.R. and Dhinojwala, A. (2017) Insight on Structure of Water and Ice Next to Graphene Using Surface-Sensitive Spectroscopy. ACS Nano, 11, 4899-4906.
https://doi.org/10.1021/acsnano.7b01499

[9]   Remyamol, T., John, H. and Gopinath, P. (2014) Synthesis and Nonlinear Optical Properties of Reduced Graphene Oxide Covalently Functionalized with Polyaniline. Carbon, 59, 308-314.
https://doi.org/10.1016/j.carbon.2013.03.023

[10]   Senge, M.O., Fazekas, M., Notraras, E.G.A., Blau, W.J., Zawadzka, M., Locos, O.B. and Mhuircheartaigh, E.M.N. (2007) Nonlinear Optical Properties of Porphyrins. Advanced Materials, 19, 2737-2774.
https://doi.org/10.1002/adma.200601850

[11]   Dini, D., Hanack, M., Kadish, K.M., Smith, K.M. and Guilard, R. (2003) The Porphyrin Handbook. Vol. 17, Academic Press, New York, 22.

[12]   Krishna, M.B.M., Venkatramaiah, N., Venkatesan, R. and Rao, D.N. (2012) Synthesis and Structural, Spectroscopic and Nonlinear Optical Measurements of Graphene Oxide and Its Composites with Metal and Metal Free Porphyrins. Journal of Materials Chemistry, 22, 3059-3068.
https://doi.org/10.1039/c1jm14822b

[13]   Liu, Z.B., Tian, J.G., Guo, Z., Ren, D.M., Du, F., Zheng, J.Y. and Chen, Y.S. (2008) Enhanced Optical Limiting Effects in Porphyrin-Covalently Functionalized Single-Walled Carbon Nanotubes. Ad-vanced Materials, 20, 511-515.
https://doi.org/10.1002/adma.200702547

[14]   Li, P.P., Chen, Y., Zhu, J., Feng, M., Zhuang, X., Lin, Y. and Zhan. H. (2011) Charm-Bracelet-Type Poly(N-Vinylcarbazole) Functionalized with Reduced Graphene Oxide for Broadband Optical Limiting. Chemistry—A European Journal, 17, 780-785.
https://doi.org/10.1002/chem.201002431

[15]   Zhang, B., Liu, G., Chen, Y., Zeng, L.J., Zhu, C.X., Neoh, K.G., Wang, C. and Kang, E.T. (2011) Conjugated Polymer-Grafted Reduced Graphene Oxide for Nonvolatile Rewritable Memory. Chemistry—A European Journal, 17, 13646-13652.
https://doi.org/10.1002/chem.201102686

[16]   Hummers, W.S. and Offeman, R.E. (1958) Preparation of Graphitic Oxide. Journal of the American Chemical Society, 80, 1339.
https://doi.org/10.1021/ja01539a017

[17]   Shen, J., Hu, Y., Li, C., Qin, C. and Ye, M. (2009) Synthesis of Amphiphilic Graphene Nanoplatelets. Small, 5, 82-85.
https://doi.org/10.1002/smll.200800988

[18]   Fu, B., Yu, H.C., Huang, J.W., Zhao, P., Liu, J. and Ji, N.L. (2009) Mn(III) Porphyrins Immobilized on Magnetic Polymer Nanospheres as Biomimetic Catalysts Hydroxylating Cyclo-hexane with Molecular Oxygen. Journal of Molecular Catalysis A: Chemical, 298, 74-80.
https://doi.org/10.1016/j.molcata.2008.10.015

[19]   Sheik-Bahae, M., Said, A.A. and Stryland, E.W. (1989) High-Sensitivity, Single-Beam n2 Measure-ments. Optics Letters, 14, 955-957.
https://doi.org/10.1364/OL.14.000955

[20]   Li, Z., Chen, Y., Du, Y., Wang, X., Yang, P. and Zheng. J. (2012) Triphenylamine-Functionalized Graphene Decorated with Pt Nanoparticles and Its Applications in Photocatalytic Hydrogen Production. International Journal of Hydrogen Energy, 37, 4880-4888.
https://doi.org/10.1016/j.ijhydene.2011.12.045

[21]   Szabó, T., Berkesi, O. and Dékány, I. (2005) DRIFT Study of Deuterium-Exchanged Graphite Oxide. Carbon, 43, 3186-3189.
https://doi.org/10.1016/j.carbon.2005.07.013

[22]   Guo, Z., Du, F., Ren, D., Chen, Y., Zheng, J., Liu, Z. and Tian, J. (2006) Covalently Porphyrin-Functionalized Single-Walled Carbon Nanotubes: A Novel Photoactive and Optical Limiting Do-nor-Acceptor Nanohybrid. Journal of Materials Chemistry, 16, 3021-3030.
https://doi.org/10.1039/B602349E

[23]   Zhang, X., Hou, L., Cnossen, A., Coleman, A.C., Ivashenko, O., Rudolf, P. and Feringa, B.L. (2011) One-Pot Functionalization of Graphene with Porphyrin through Cycloaddition Reactions. Chemistry: A European Journal, 17, 8957-8964.
https://doi.org/10.1002/chem.201100980

[24]   Castelaín, M., Martínez, G., Merino, P., Martín-Gago, J.á., Segura, J.L., Ellis, G. and Salavagione, H.J. (2012) Graphene Functionalization with a Conjugated Poly(Fluorene) by Click Coupling: Striking Electronic Properties in Solution. Chemistry: A European Journal, 18, 4965-4973.
https://doi.org/10.1002/chem.201102008

[25]   Cho, S., Lim, J.M., Hiroto, S., Kim, P., Shinokubo, H., Osuka, A. and Kim, D. (2009) Unusual Interchromophoric Interactions in β’ Directly and Doubly Linked Corroledimmers: Prohibited Electronic Communication and Abnormal Singlet Ground States. Journal of the American Chemical Society, 131, 6412-6420.
https://doi.org/10.1021/ja900220y

[26]   Zhong, Q., Diev, V.V., Roberts, S.T., Antunez, P.D., Brutchey, R.L., Bradforth, S.E. and Thompson, M.E. (2013) Fused Porphyrin-Single-Walled Carbon Nanotube Hybrids: Efficient Formation and Photophysical Characterization. ACS Nano, 7, 3466-3475.
https://doi.org/10.1021/nn400362e

[27]   Finikova, O.S., Troxler, T., Senes, A., DeGrado, W.F., Hochstrasser, R.M. and Vinogradov, S.A. (2007) Energy and Electron Transfer in Enhanced Two-Photon-Absorbing Systems with Triplet Cores. The Journal of Physical Chemistry A, 111, 6977-6990.
https://doi.org/10.1021/jp071586f

[28]   Liu, Z.B., Xu, Y.F., Zhang, X.Y., Zhang, X.L., Chen, Y.S. and Tian, J.G. (2009) Porphyrin and Fullerene Covalently Functionalized Graphene Hybrid Materials with Large Nonlinear Optical Properties. The Journal of Physical Chemistry B, 113, 9681-9686.
https://doi.org/10.1021/jp9004357

[29]   Gong, F., Xu, X., Zhou, G. and Wang, Z.S. (2013) Enhanced Charge Transportation in a Polyrrole Counter Electrode via Incorporation of Reduced Graphene Oxide Sheets for Dye-Sensitized Solar Cells. Physical Chemistry Chemical Physics, 15, 546-552.
https://doi.org/10.1039/C2CP42790G

[30]   Zhang, B., Chen, Y., Liu, G., Xu, L.Q., Chen, J., Zhu, C.X., Neoh, K.G. and Kang, E.T. (2012) Push-Pull Archetype of Reduced Graphene Oxide Functionalization with Polyfluorene for Nonvolatile Rewritable Memory. Journal of Polymer Science Part A: Polymer Chemistry, 50, 378-387.
https://doi.org/10.1002/pola.25043

[31]   Kavitha, M.K., John, H., Gopinath, P. and Philip, R. (2013) Synthesis of Reduced Graphene Oxide-ZnO Hybrid with Enhanced Optical Limiting Properties. Journal of Materials Chemistry C, 1, 3669-3676.
https://doi.org/10.1039/c3tc30323c

[32]   Paredes, J.I., Villar-Rodil. S., Solís-Fernández, P., Martínez-Alonso, A. and Tascón, J.M.D. (2009) Atomic Force and Scanning Tuning Microscopy Imaging of Graphenenanosheets Derived from Graphite Oxide. Langmuir, 25, 5957-5968.
https://doi.org/10.1021/la804216z

[33]   Hsiao, M.C., Liao, S.H., Yen, M.Y., Liu, P.I., Pu, N.W., Wang, C.A. and Ma, C.C.M. (2010) Preparation of Covalently Functionalization Graphene Using Residual Oxygen-Containing Functional Groups. ACS Applied Materials & Interfaces, 2, 3092-3099.
https://doi.org/10.1021/am100597d

[34]   Zhang, X., Feng, Y., Tang, S. and Feng, W. (2010) Preparation of a Graphene Oxide-Phthalocyanine Hybrid through Strong π-π Interactions. Carbon, 48, 211-216.
https://doi.org/10.1016/j.carbon.2009.09.007

[35]   Wang, J., Hernandez, Y., Lotya, M., Coleman, J.N. and Blau, W.J. (2009) Broadband Nonlinear Optical Response of Graphene Dispersions. Advanced Materials, 21, 2430-2435.
https://doi.org/10.1002/adma.200803616

[36]   Kost, A. and Tutt, L.W. (1992) Optical Limiting Performance of C60 and C70 Solutions. Nature, 356, 225-226.
https://doi.org/10.1038/356225a0

[37]   Liu, Z.B., Guo, Z., Zhang, X.L., Zheng, J.Y. and Tian, J.G. (2013) Increased Optical Nonlinearities of Multi-Walled Carbon Nanotubes Covalently Functionalized with Porphyrin. Carbon, 51, 419-426.
https://doi.org/10.1016/j.carbon.2012.09.005

[38]   Balapanuru, J., Yang, J.X., Xiao, S., Bao, Q.L., Jahan, M., Polavarapu, L., Wei, J., Xu, Q.H. and Loh, K.P. (2012) A Graphene Oxide-Organic Dye Ionic Complex with DNA-Sensing and Optical-Limiting Properties. Angewandte Chemie International Edition, 49, 6549-6553.
https://doi.org/10.1002/anie.201001004

[39]   Jiang, X.F., Polavarapu, L., Neo, S.T., Venkatesan, T. and Xu, Q.H. (2012) Graphene Oxides as Tunable Broadband Nonlinear Optical Materials for Femtosecond Laser Pulses. The Journal of Physical Chemistry Letters, 3, 785-790.
https://doi.org/10.1021/jz300119t

[40]   Song, W.N., He, C.Y., Zhang, W., Gao, Y.C., Yang, Y.X., Wu, Y.Q., Chen, Z.M., Li, X.C. and Dong, Y.L. (2014) Synthesis and Nonlinear Optical Properties of Reduced Graphene Oxide Hybrid Material Covalently Functionalized with Zinc Phthalocyanine. Carbon, 77, 1020-1030.
https://doi.org/10.1016/j.carbon.2014.06.018

[41]   Xu, Y.F., Liu, Z.B., Zhang, X.L., Wang, Y., Tian, J.G., Huang, Y., Ma, Y.F., Zhang, X.Y. and Chen, Y.S. (2009) A Graphene Hybrid Material Covalently Functionalized with Porphyrin: Synthesis and Optical Limiting Property. Advanced Materials, 21, 1275-1279.
https://doi.org/10.1002/adma.200801617

[42]   Wang, J., Chen, Y. and Blau, W.J. (2009) Carbon Nanotubes and Nanotube Composites for Non-linear Optical Devices. Journal of Materials Chemistry, 19, 7425-7443.
https://doi.org/10.1039/b906294g

 
 
Top