Abstract
Porphyrins are an important class of conjugated organic molecules, which can be employed to mimic the active site of many important enzymes, such as hemoglobin, myoglobin, cytochrome c oxidase (CcO), nitric oxide reductase, vitamin B12, and chlorophyll [1–3]. The macrocyclic structure of porphyrin can conjugate many metal elements to form stable metalloporphyrins, which have remarkable photo-, catalytic-, electro-, and biochemical properties. Among these complexes, iron porphyrins can be used well as electron media based on the reversible redox of Fe3+/Fe2+ and exhibit good electrocatalysis to many small molecules related to life processes [4, 5], including dissolved oxygen, NO, neurotransmitters, hydrogen peroxide, and nitrite. On the other hand, high-valent iron(IV)–porphyrin as a strong oxidant has been utilized to catalyze the mono-oxygenation of organic substrates and biomolecules in many chemical reactions [6, 7].
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Balaban, T.S., Linke-Schaetzel, M., Bhise, A.D., et al.: Structural characterization of artificial self-assembling porphyrins that mimic the natural chlorosomal bacteriochlorophylls c, d, and e. Chem. Eur. J. 11, 2267–2275 (2005)
Collman, J.P., Yan, Y.L., Lei, J.P., et al.: Active-site models of bacterial nitric oxide reductase featuring tris-histidyl and glutamic acid mimics: influence of a carboxylate ligand on Fe-B binding and the heme Fe/Fe-B redox potential. Inorg. Chem. 45, 7581–7583 (2006)
Collman, J.P., Devaraj, N.K., Decreau, R.A., et al.: A cytochrome c oxidase model catalyzes oxygen to water reduction under rate-limiting electron flux. Science 315, 1565–1568 (2007)
Steiger, B., Anson, F.C.: Examination of cobalt “picket fence” porphyrin and its complex with 1-methylimidazole as catalysts for the electroreduction of dioxygen. Inorg. Chem. 39, 4579–4585 (2000)
Collman, J.P., Boultaov, R., Sunderland, C.J., et al.: Electrochemical metalloporphyrin-catalyzed reduction of chlorite. J. Am. Chem. Soc. 124, 10670–10671 (2002)
Lei, J.P., Ju, H.X., Ikeda, O.: Catalytic oxidation of nitric oxide and nitrite mediated by water-soluble high-valent iron porphyrins at an ITO electrode. J. Electroanal. Chem. 567, 331–338 (2004)
Takahashi, A., Kurahashi, T., Fujii, H.: Effect of imidazole and phenolate axial ligands on the electronic structure and reactivity of oxoiron(IV) porphyrin π-cation radical complexes: drastic increase in oxo-transfer and hydrogen abstraction reactivities. Inorg. Chem. 48, 2614–2625 (2009)
Collman, J.P., Boulatov, R., Sunderland, C.J., et al.: Functional analogues of cytochrome c oxidase, myoglobin, and hemoglobin. Chem. Rev. 104, 561–588 (2004)
Tu, W.W., Lei, J.P., Ju, H.X.: Noncovalent nanoassembly of porphyrin on single-walled carbon nanotubes for electrocatalytic reduction of nitric oxide and oxygen. Electrochem. Commun. 10, 766–769 (2008)
Tu, W.W., Lei, J.P., Ju, H.X.: Functionalization of carbon nanotubes with water-insoluble porphyrin in ionic liquid: direct electrochemistry and highly sensitive amperometric biosensing for trichloroacetic acid. Chem. Eur. J. 15, 779–784 (2009)
Murakami, H., Nomura, T., Nakashima, N.: Noncovalent porphyrin-functionalized single-walled carbon nanotubes in solution and the formation of porphyrin–nanotube nanocomposites. Chem. Phys. Lett. 378, 481–485 (2003)
Zhao, J.X., Ding, Y.H.: Functionalization of single-walled carbon nanotubes with metalloporphyrin complexes: a theoretical study. J. Phys. Chem. C 112, 11130–11134 (2008)
Li, H.P., Zhou, B., Lin, Y., et al.: Selective interactions of porphyrins with semiconducting single-walled carbon nanotubes. J. Am. Chem. Soc. 126, 1014–1015 (2004)
Hasobe, T., Fukuzumi, S., Kamat, P.V.: Ordered assembly of protonated porphyrin driven by single-wall carbon nanotubes: J- and H-aggregates to nanorods. J. Am. Chem. Soc. 127, 11884–11885 (2005)
Alvaro, M., Atienzar, P., Cruz, P.D.L., et al.: Synthesis, photochemistry, and electrochemistry of single-wall carbon nanotubes with pendent pyridyl groups and of their metal complexes with zinc porphyrin comparison with pyridyl-bearing fullerenes. J. Am. Chem. Soc. 128, 6626–6635 (2006)
Yu, J.X., Mathew, S., Flavel, B.S., et al.: Ruthenium porphyrin functionalized single-walled carbon nanotube arrays – a step toward light harvesting antenna and multibit information storage. J. Am. Chem. Soc. 130, 8788–8796 (2008)
Chitta, R., Sandanayaka, A.S.D., Schumacher, A.L., et al.: Donor-acceptor nanohybrids of zinc naphthalocyanine or zinc porphyrin noncovalently linked to single-wall carbon nanotubes for photoinduced electron transfer. J. Phys. Chem. C 111, 6947–6955 (2007)
Tu, W.W., Lei, J.P., Jian, G.Q., et al.: Noncovalent assembly of picket-fence porphyrin on nitrogen-doped carbon nanotubes for highly efficient catalysis and biosensing. Chem. Eur. J. 16, 4120–4126 (2010)
Liu, Z.B., Tian, J.G., Guo, Z., et al.: Enhanced optical limiting effects in porphyrin-covalently functionalized single-walled carbon nanotubes. Adv. Mater. 20, 511–515 (2008)
Baskaran, D., Mays, J.W., Zhang, X.P., et al.: Carbon nanotubes with covalently linked porphyrin antennae: photoinduced electron transfer. J. Am. Chem. Soc. 127, 6916–6917 (2005)
Chen, J.Y., Collier, C.P.: Noncovalent functionalization of single-walled carbon nanotubes with water-soluble porphyrins. J. Phys. Chem. B 109, 7605–7609 (2005)
Guldi, D.M., Rahman, G.M.A., Jux, N., et al.: Functional single-wall carbon nanotube nanohybridd-associating SWNTs with water-soluble enzyme model systems. J. Am. Chem. Soc. 127, 9830–9838 (2005)
Ehli, C., Rahman, G.M.A., Jux, N., et al.: Interactions in single wall carbon nanotubes/pyrene/porphyrin nanohybrids. J. Am. Chem. Soc. 128, 11222–11231 (2006)
Guldi, D.M., Rahman, G.M.A., Prato, M., et al.: Single-wall carbon nanotubes as integrative building blocks for solar-energy conversion. Angew. Chem. Int. Ed. 44, 2015–2018 (2005)
Yu, P., Yan, J., Zhao, H., et al.: Rational functionalization of carbon nanotube/ionic liquid bucky gel with dual tailor-made electrocatalysts for four-electron reduction of oxygen. J. Phys. Chem. C 112, 2177–2182 (2008)
Zhang, W., Shaikh, A.U., Tsui, E.Y., et al.: Cobalt porphyrin functionalized carbon nanotubes for oxygen reduction. Chem. Mater. 21, 3234–3241 (2009)
Dembinska, B., Kulesza, P.J.: Multi-walled carbon nanotube-supported tungsten oxide-containing multifunctional hybrid electrocatalytic system for oxygen reduction in acid medium. Electrochim. Acta 54, 4682–4687 (2009)
Liu, Y., Yan, Y.L., Lei, J.P., et al.: Functional multiwalled carbon nanotube nanocomposite with iron picket-fence porphyrin and its electrocatalytic behavior. Electrochem. Commun. 9, 2564–2570 (2007)
Kowalewska, B., Skunik, M., Karnicka, K., et al.: Enhancement of bio-electrocatalytic oxygen reduction at the composite film of cobalt porphyrin immobilized within the carbon nanotube-supported peroxidase enzyme. Electrochim. Acta 53, 2408–2415 (2008)
Turdean, G.L., Popescu, I.C., Curulli, A., et al.: Iron(III) protoporphyrin IX – single-wall carbon nanotubes modified electrodes for hydrogen peroxide and nitrite detection. Electrochim. Acta 51, 6435–6441 (2006)
Lin, Z.Y., Chen, J.H., Chi, Y.W., et al.: Electrochemiluminescent behavior of luminol on the glassy carbon electrode modified with CoTPP/MWNT composite film. Electrochim. Acta 53, 6464–6468 (2008)
Huang, C.Z., Liao, Q.G., Li, Y.F.: Non-covalent anionic porphyrin functionalized multi-walled carbon nanotubes as an optical probe for specific DNA detection. Talanta 75, 163–166 (2008)
Wu, Y.H.: Electrocatalysis and sensitive determination of Sudan I at the single-walled carbon nanotubes and iron(III)-porphyrin modified glassy carbon electrodes. Food Chem. 121, 580–584 (2010)
Luz, R.C.S., Damos, F.S., Tanaka, A.A., et al.: Electrocatalysis of reduced L-glutathione oxidation by iron(III) tetra-(N-methyl-4-pyridyl)-porphyrin (FeT4MPyP) adsorbed on multi-walled carbon nanotubes. Talanta 76, 1097–1104 (2008)
Pagona, G., Sandanayaka, A.S.D., Araki, Y., et al.: Electronic interplay on illuminated aqueous carbon nanohorn-porphyrin ensembles. J. Phys. Chem. B 110, 20729–20732 (2006)
Pagona, G., Fan, J., Maignè, A., et al.: Aqueous carbon nanohorn–pyrene–porphyrin nanoensembles: controlling charge-transfer interactions. Diam. Relat. Mater. 16, 1150–1153 (2007)
Tu, W.W., Lei, J.P., Ding, L., et al.: Sandwich nanohybrid of single-walled carbon nanohorns–TiO2–porphyrin for electrocatalysis and amperometric biosensing towards chloramphenicol. Chem. Commun. 28, 4227–4229 (2009)
Xu, Y.F., Liu, Z.B., Zhang, X.L., et al.: A graphene hybrid material covalently functionalized with porphyrin: synthesis and optical limiting property. Adv. Mater. 21, 1275–1279 (2009)
Xu, Y.X., Zhao, L., Bai, H., et al.: Chemically converted graphene induced molecular flattening of 5,10,15,20-tetrakis(1-methyl-4-pyridinio)porphyrin and its application for optical detection of cadmium(II) ions. J. Am. Chem. Soc. 131, 13490–13497 (2009)
Tu, W.W., Zhang, S.Y., Lei, J.P., et al.: Characterization, direct electrochemistry and amperometric biosensing of graphene by noncovalent functionalization with picket-fence porphyrin. Chem. Eur. J. 16, 10771–10777 (2010)
Rochford, J., Chu, D., Hagfeldt, A., et al.: Tetrachelate porphyrin chromophores for metal oxide semiconductor sensitization: effect of the spacer length and anchoring group position. J. Am. Chem. Soc. 129, 4655–4665 (2007)
Rochford, J., Galoppini, E.: Zinc(II) tetraarylporphyrins anchored to TiO2, ZnO, and ZrO2 nanoparticle films through rigid-rod linkers. Langmuir 24, 5366–5374 (2008)
Brumbach, M.T., Boal, A.K., Wheeler, D.R.: Metalloporphyrin assemblies on pyridine-functionalized titanium dioxide. Langmuir 25, 10685–10690 (2009)
Yang, X.J., Dai, Z.F., Miura, A.: Different back electron transfer from titanium dioxide nanoparticles to tetra (4-sulfonatophenyl) porphyrin monomer and its J-aggregate. Chem. Phys. Lett. 334, 257–264 (2001)
Marczak, R., Werner, F., Gnichwitz, J.F., et al.: Communication via electron and energy transfer between zinc oxide nanoparticles and organic adsorbates. J. Phys. Chem. C 113, 4669–4678 (2009)
Yang, C., Yang, Z.M., Gu, H.W.: Facet-selective 2D self-assembly of TiO2 nanoleaves via supramolecular interactions. Chem. Mater. 20, 7514–7520 (2008)
Yu, J.H., Chen, J.R., Wang, X.S., et al.: Porphyrin capped TiO2 nanoclusters, tyrosine methyl ester enhanced electron transfer. Chem. Commun. 15, 1856–1857 (2003)
Hasobe, T., Fukuzumi, S., Hattori, S., et al.: Shape- and functionality-controlled organization of TiO2–porphyrin–C60 assemblies for improved performance of photochemical solar cells. Chem. Asian J. 2, 265–272 (2007)
Chen, D.M., Yang, D., Geng, J.Q., et al.: Improving visible-light photocatalytic activity of N-doped TiO2 nanoparticles via sensitization by Zn porphyrin. Appl. Surf. Sci. 255, 2879–2884 (2008)
Imahori, H., Hayashi, S., Umeyama, T., et al.: Comparison of electrode structures and photovoltaic properties of porphyrin-sensitized solar cells with TiO2 and Nb, Ge, Zr-Added TiO2 composite electrodes. Langmuir 22, 11405–11411 (2006)
El-Deab, M.S., Othman, S.H., Okajima, T., et al.: Non-platinum electrocatalysts: manganese oxide nanoparticle-cobaltporphyrin binary catalysts for oxygen reduction. J. Appl. Electrochem. 38, 1445–1451 (2008)
Ikeda, A., Tsuchiya, Y., Konishi, T., et al.: Photocurrent-boosting by intramembrane electron mediation between titania nanoparticles dispersed into nafion-porphyrin composites. Chem. Mater. 17, 4018–4022 (2005)
Castellani, A.M., Gushikem, Y.: Electrochemical properties of a porphyrin-cobalt (II) adsorbed on silica–titania–phosphate composite surface prepared by the sol–gel method. J. Colloid Interface Sci. 230, 195–199 (2000)
Dias, S.L.P., Gushikem, Y., Ribeiro, E.S., et al.: Cobalt(II) hematoporphyrin IX and protoporphyrin IX complexes immobilized on highly dispersed titanium(IV) oxide on a cellulose microfiber surface: electrochemical properties and dissolved oxygen reduction study. J. Electroanal. Chem. 523, 64–69 (2002)
Francisco, M.S.P., Cardoso, W.S., Kubota, L.T., et al.: Electrocatalytic oxidation of phenolic compounds using an electrode modified with Ni(II) porphyrin adsorbed on SiO2/Nb2O5-phosphate synthesized by the sol–gel method. J. Electroanal. Chem. 602, 29–36 (2007)
Zenkevich, E.I., Blaudeck, T., Shulga, A.M., et al.: Identification and assignment of porphyrin–CdSe hetero-nanoassemblies. J. Luminesc. 122–123, 784–788 (2007)
Zenkevich, E., Cichos, F., Shulga, A., et al.: Nanoassemblies designed from semiconductor quantum dots and molecular arrays. J. Phys. Chem. B 109, 8679–8692 (2005)
Li, X.Q., Mu, J., Li, F., et al.: Self-assembly and optical properties of water-soluble porphyrin alternating CdSe nanoparticulate films. Colloid Surf. A 260, 239–243 (2005)
Jhonsi, M.A., Renganathan, R.: Investigations on the photoinduced interaction of water soluble thioglycolic acid (TGA) capped CdTe quantum dots with certain porphyrins. J. Colloid Interface Sci. 344, 596–602 (2010)
Gu, H.W., Xu, K.M., Yang, Z.M., et al.: Synthesis and cellular uptake of porphyrin decorated iron oxide nanoparticles – a potential candidate for bimodal anticancer therapy. Chem. Commun. 34, 4270–4272 (2005)
Ohyama, J., Hitomi, Y., Higuchi, Y., et al.: One-phase synthesis of small gold nanoparticles coated by a horizontal porphyrin monolayer. Chem. Commun. 47, 6300–6302 (2008)
Cormode, D.P., Davis, J.J., Beer, P.D.: Anion sensing porphyrin functionalized nanoparticles. J. Inorg. Organomet. Polym. 18, 32–40 (2008)
Fantuzzi, G., Pengo, P., Gomila, R., et al.: Multivalent recognition of bis- and tris-Zn-porphyrins by N-methylimidazole functionalized gold nanoparticles. Chem. Commun. 8, 1004–1005 (2003)
Hasobe, T., Imahori, H., Kamat, P.V., et al.: Photovoltaic cells using composite nanoclusters of porphyrins and fullerenes with gold nanoparticles. J. Am. Chem. Soc. 127, 1216–1228 (2005)
Imahori, H., Arimura, M., Hanada, T., et al.: Photoactive three-dimensional monolayers: porphyrin-alkanethiolate-stabilized gold clusters. J. Am. Chem. Soc. 123, 335–336 (2001)
Yamada, M., Kuzume, A., Kurihara, M.: Formation of a novel porphyrin–gold nanoparticle network film induced by IR light irradiation. Chem. Commun. 23, 2476–2477 (2001)
Satake, A., Fujita, M., Kurimoto, Y., et al.: Single supramolecular porphyrin wires bridging gold nanoparticles. Chem. Commun. 10, 1231–1233 (2009)
Murakami, Y., Konishi, K.: Remarkable co-catalyst effect of gold nanoclusters on olefin oxidation catalyzed by a manganese-porphyrin complex. J. Am. Chem. Soc. 129, 14401–14407 (2007)
Huang, M.H., Shen, Y., Cheng, W.L., et al.: Nanocomposite films containing Au nanoparticles formed by electrochemical reduction of metal ions in the multilayer films as electrocatalyst for dioxygen reduction. Anal. Chim. Acta 535, 15–22 (2005)
Damos, F.S., Luz, R.C.S., Tanaka, A.A., et al.: Dissolved oxygen amperometric sensor based on layer-by-layer assembly using host-guest supramolecular interactions. Anal. Chim. Acta 664, 144–150 (2010)
Gong, F.C., Xiao, Z.D., Cao, Z., et al.: A selective artemisinin-sensor using metalloporphyrin as a recognition element entrapped in the Au-nanoparticles-chitosan modified electrodes. Talanta 72, 1453–1457 (2007)
Molnár, P., Procházka, M.: SER(R)S of porphyrins on Ag nanoparticles immobilized by silane: a unique way to obtain free-base porphyrin spectra. J. Raman Spectrosc. 38, 799–801 (2007)
Hajduková, N., Procházka, M., Molnár, P., et al.: SERRS of free-base porphyrins on immobilized metal gold and silver nanoparticles. Vib. Spectrosc. 48, 142–147 (2008)
Arakawa, T., Munaoka, T., Akiyama, T., et al.: Effects of silver nanoparticles on photoelectrochemical responses of organic dyes. J. Phys. Chem. C 113, 11830–11835 (2009)
Zhu, M.S., Han, M., Du, Y.K., et al.: The synthesis, light-harvesting, and photocatalysis of naphthylporphyrin-functionalized platinum nanocomposites. Dyes Pigm. 86, 81–86 (2010)
Huang, M.H., Shao, Y., Sun, X.P., et al.: Alternate assemblies of platinum nanoparticles and metalloporphyrins as tunable electrocatalysts for dioxygen reduction. Langmuir 21, 323–329 (2005)
Shen, Y., Liu, J.Y., Wu, A.G., et al.: Preparation of multilayer films containing Pt nanoparticles on a glassy carbon electrode and application as an electrocatalyst for dioxygen reduction. Langmuir 19, 5397–5401 (2003)
Wiyaratn, W., Hrapovic, S., Liu, Y.L., et al.: Light-assisted synthesis of Pt-Zn porphyrin nanocomposites and their use for electrochemical detection of organohalides. Anal. Chem. 77, 5742–5749 (2005)
Xing, C.F., Xu, Q.L., Tang, H.G., et al.: Conjugated polymer/porphyrin complexes for efficient energy transfer and improving light-activated antibacterial activity. J. Am. Chem. Soc. 131, 13117–13124 (2009)
Bédard, M.F., Sadasivan, S., Sukhorukov, G.B., et al.: Assembling polyelectrolytes and porphyrins into hollow capsules with laser-responsive oxidative properties. J. Mater. Chem. 19, 2226–2233 (2009)
Carballo, R.R., Orto, V.C., Hurst, J.A., et al.: Covalently attached metalloporphyrins in LBL self-assembled redox polyelectrolyte thin films. Electrochim. Acta 53, 5215–5219 (2008)
Wu, C.F., Bull, B., Christensen, K., et al.: Ratiometric single-nanoparticle oxygen sensors for biological imaging. Angew. Chem. Int. Ed. 48, 2741–2745 (2009)
Cywinski, P.J., Moro, A.J., Stanca, S.E., et al.: Ratiometric porphyrin-based layers and nanoparticles for measuring oxygen in biosamples. Sens. Actuat. B Chem. 135, 472–477 (2009)
Yan, Q., Yuan, J.Y., Kang, Y., et al.: Dual-sensing porphyrin-containing copolymer nanosensor as full-spectrum colorimeter and ultra-sensitive thermometer. Chem. Commun. 46, 2781–2783 (2010)
Fu, B., Yu, H.C., Huang, J.W., et al.: Mn(III) porphyrins immobilized on magnetic polymer nanospheres as biomimetic catalysts hydroxylating cyclohexane with molecular oxygen. J. Mol. Catal. A Chem. 298, 74–80 (2009)
Fagadar-Cosma, E., Enache, C., Vlascici, D., et al.: Novel nanomaterials based on 5,10,15,20-tetrakis(3,4-dimethoxyphenyl)-21H,23H-porphyrin entrapped in silica matrices. Mater. Res. Bull. 44, 2186–2193 (2009)
Rossi, L.M., Silva, P.R., Vono, L.L.R., et al.: Protoporphyrin IX nanoparticle carrier: preparation, optical properties, and singlet oxygen generation. Langmuir 24, 12534–12538 (2008)
Liang, S., Hartvickson, S., Kozliak, E., et al.: Effect of amorphous silica nanomatrix on kinetics of metalation of encapsulated porphyrin molecules. J. Phys. Chem. C 113, 19046–19054 (2009)
Tao, S.Y., Li, G.T.: Porphyrin-doped mesoporous silica films for rapid TNT detection. Colloid Polym. Sci. 285, 721–728 (2007)
Winkelmann, C.B., Ionica, I., Chevalier, X., et al.: Optical switching of porphyrin-coated silicon nanowire field effect transistors. Nano Lett. 7, 1454–1458 (2007)
Ganesan, K., Kovtun, A., Neumann, S., et al.: Calcium phosphate nanoparticles: colloidally stabilized and made fluorescent by a phosphate-functionalized porphyrin. J. Mater. Chem. 18, 3655–3661 (2008)
Palacin, T., Khanh, H.L., Jousselme, B., et al.: Efficient functionalization of carbon nanotubes with porphyrin dendrons via click chemistry. J. Am. Chem. Soc. 131, 15394–15402 (2009)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2011 Springer Science+Business Media, LLC
About this chapter
Cite this chapter
Ju, H., Zhang, X., Wang, J. (2011). Porphyrin-Based Nanocomposites for Biosensing. In: NanoBiosensing. Biological and Medical Physics, Biomedical Engineering. Springer, New York, NY. https://doi.org/10.1007/978-1-4419-9622-0_4
Download citation
DOI: https://doi.org/10.1007/978-1-4419-9622-0_4
Published:
Publisher Name: Springer, New York, NY
Print ISBN: 978-1-4419-9621-3
Online ISBN: 978-1-4419-9622-0
eBook Packages: Physics and AstronomyPhysics and Astronomy (R0)