Recent advances in Porphyrin-Derived sensors

Current Organic Chemistry

Volumn 17, Issue 24, 2013, Pages 3078-3091

  Wang, Lingyun ^a   Li, Huihui ^a   Deng, Jiacheng ^a   Cao, Derong ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Fluorescence; Porphyrins; Sensor; UV vis

Indexed keywords

CHROMATOGRAPHIC ANALYSIS; LANGMUIR BLODGETT FILMS; LIGHT SCATTERING; METAL IONS; PORPHYRINS;

FLUORESCENCE METHOD; HIGH SENSITIVITY; LEADING TECHNOLOGY; METALS IONS; PHOTOPHYSICAL CHARACTERISTICS; PROPERTY; REPRODUCIBILITIES; RESPONSE AND RECOVERY TIME; TETRAPYRROLIC MACROCYCLES; UV-VIS;

FLUORESCENCE;

EID: 84890871374     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/13852728113179990024     Document Type: Article

References (85)

1. Zakavi, S.; Karimipour, G. R.; Gharab, N. G. Meso-tetraarylporphyrin catalyzed highly regioselective ring opening of epoxides with acetic acid. Catal. Comm., 2009, 10, 388-390.
2. Berkessel, A., Erturk, E., Laporte, C. Chiral chromium(III) porphyrins as highly enantioselective catalysts for hetero-DielseAlder reactions between aldehydes and dienes. Adv. Syn. Catal., 2006, 348, 223-228.
3. Handbook of Porphyrin Science, ed. K. M. Kadish, K. M. Smith and R. Guilard, World Scientific, Singapore, 2010.
4. Giancane, G.; Valli, L. State of art in porphyrin Langmuir-Blodgett films as chemical sensors. Adv. Colloid Interfac., 2012, 171-172, 17-35.
5. Ethirajan, M.; Chen, Y. H.; Joshi P.; Pandey, R. K. The role of porphyrin chemistry in tumor imaging and photodynamic therapy. Chem. Soc. Rev., 2011, 40, 340-362.
6. Lovell, J. F.; Liu, T. W. B.; Chen J.; Zheng G. Activatable Photosensitizers for Imaging and Therapy, Chem. Rev., 2010, 110, 2839-2857.
7. Wang, L. Y.; Cao, D. R. Research Advances of Porphyrin Photosensitizers in Photodynamic Therapy. Chinese J. Org. Chem., (in press, DOI 10.6023/cjoc201205036).
8. van Staden, J F.; Staden, R. I. S. Application of porphyrins in flow-injection analysis: A review. Talanta, 2010, 80, 1598-1605.
9. Senge, M. O. Stirring the porphyrin alphabet soup-functionalization reactions for porphyrins. Chem. Commun., 2011, 47, 1943-1960.
10. Mamardashvili, N. Z.; Maltseva, O. V.; Ivanova, Y. B.; Mamardashvili, G. M. Porphyrin-based molecular receptors for alkali metal cations: synthesis and chemical modification. Tetrahedron Lett., 2008, 49, 3752-3756.
11. 2+ with high selectivity. Anal. Chim. Acta, 2008, 616, 214-221.
12. Xu, Y. X.; Zhao, L.; Bai, H.; Hong, W. J.; Li, C.; Shi, G. Q. Chemically converted graphene induced molecular flattening of 5,10,15,20-tetrakis(1methyl-4-pyridinio)porphyrin and its application for optical detection of cadmium(II) ions. J. Am. Chem. Soc., 2009, 131, 13490-13497.
13. Yang, Y.; Jiang, J. H.; Shen, G. L.; Yu, R. Q. An optical sensor for mercury ion based on the fluorescence quenching of tetra(pdimethylaminophenyl)porphyrin. Anal. Chim. Acta, 2009, 636, 83-88.
14. Li, T.; Wang, E. K.; Dong, S. J. Parallel G-quadruplex-specific fluorescent probe for monitoring DNA structural changes and label-free detection of potassium ion. Anal. Chem., 2010, 82, 7576-7580.
15. Fang, Z.; Liu, B. A cationic porphyrin-based self-assembled film for mercury ion detection. Tetrahedron Lett., 2008, 49, 2311-2315.
16. Fang, Z.; Pu, K. Y.; Liu, B. Asymmetric fluorescence quenching of dualemissive porphyrin-containing conjugated polyelectrolytes for naked-eye mercury ion detection, Macromolecules, 2008, 41, 8380-8387.
17. 2+ based on a new porphyrin-quinoline dyad. Spectrochim. Acta A, 2009, 72, 1084-1088.
18. 2+: well-resolved emission spectra and unique specificity, Anal. Chem., 2009, 81, 9993-10001.
19. Frasco, M. F.; Vamvakaki, V.; Chaniotakis, N. Porphyrin decorated CdSe quantum dots for direct fluorescent sensing of metal ions. J. Nanopart. Res., 2010, 12, 1449-1458.
20. Li, C. Y.; Xu, F.; Li, Y. F. A fluorescent chemosensor for silver ions based on porphyrin compound with high selectivity. Spectrochim. Acta A, 2010, 76, 197-201.
21. Kumar, P.; Shim, Y. B. A novel Mg(II)-selective sensor based on 5,10,15,20tetrakis(2-furyl)-21, 23-dithiaporphyrin as an electroactive material. J. Electroanal. Chem., 2011, 661, 25-30.
22. Hu, S.; Mao, H. S.; Wang, Y. Optical sensing of heavy metal ions in anionic micellar solution using a Pd porphyrin phosphorescent probe. J. Photochem Photobio. A: Chem., 2009, 204, 1-6.
23. Bozkurt, S. S.; Ayata, S.; Kaynak, I. Fluorescence-based sensor for Pb(II) using tetra-(3-bromo-4-hydroxyphenyl)porphyrin in liquid and immobilized medium. Spectrochim. Acta A, 2009, 72, 880-883.
24. Ishida, M.; Naruta, Y.; Tani, F. A Porphyrin-related macrocycle with an embedded 1,10-phenanthroline moiety: fluorescent magnesium(II) ion sensor. Angew. Chem. Int. Ed., 2010, 49, 91-94.
25. 2+. Org. Biomol. Chem., 2012, 10, 4782-4787.
26. Asano, T.; Wang, P. C.; Iwasaki, A. Synthesis of porphyrin-incorporated polymers and their application for simultaneous detection of multimetal components by using spectrophotometry, Spectrochim. Acta A, 2010, 75, 305-309.
27. Supriyatno H.; Yamashita M.; Nakagawa K.; Sadaoka Y. Optochemical sensor for HCl gas based on tetraphenylporphyrin dispersed in styreneacrylate copolymers: effect of glass transition temperature of matrix on HCl detection. Sens. Actuators B: Chem., 2002, 85, 197-204.
28. Nakagawa, K.; Kumon, K.; Tsutsumi, C.; Tabuchi, K.; Kitagawa, T.; Sadaoka, Y. HCl gas sensing properties of TPPH2 dispersed in various copolymers. Sens. Actuators B: Chem., 2000, 65, 138-140.
29. Nakagawa, K.; Sadaoka, Y.; Supriyatno, H.; Kubo, A.; Tsutsumi, C.; Tabuchi, K. Optochemical HCl gas detection using alkoxy substituted tetraphenylporphyrin polymer composite films: effect of alkoxy chain length on sensing characteristics. Sens. Actuators B: Chem., 2001, 76, 42-46.
30. Nakagawa, K.; Tanaka, K.; Kitagawa, T.; Sadaoka, Y. Optochemical HCl gas sensor using substituted tetraphenylporphine-ethylcellulose composite films. J. Mater. Chem., 1998, 8, 1199-1204.
31. Itagaki, Y.; Deki, K.; Nakashima, S. I.; Sadaoka, Y. Toxic gas detection using porphyrin dispersed polymer composites, Sens. Actuators B: Chem., 2005, 108, 393-397.
32. Nakagawa, K.; Aono, T.; Ueda, G.; Tsutsumi, C.; Hayase, N.; Mabuchi, M.; Sadaoka, Y. Development of an eco-friendly optical sensor element based on tetraphenylporphyrin derivatives dispersed in biodegradable polymer: effects of substituents of tetraphenyl-porphyrins on HCl detection and biodegradation. Sens. Actuators B: Chem., 2005, 108, 542-546.
33. Supriyatno, H.; Nakagawa, K.; Sadaoka, Y. Optochemical HCl gas detection using mono-substituted tetraphenylporphin-polymer composite films. Sens. Actuators B: Chem., 2001, 76, 36-41.
34. Itagaki, Y.; Deki, K.; Nakashima, S. I.; Sadaoka, Y. Development of porphyrin dispersed sol-gel films as HCl sensitive optochemical gas sensor. Sens. Actuators B: Chem., 2006, 117, 302-307.
35. Wan, L.S.; Wu, J.; Xu, Z. K. Porphyrinated nanofibers via copolymerization and electrospinning. Macromol. Rapid Commun., 2006, 27, 1533-1538.
36. Lv, Y.Y.; Wu, J.; Wan, L.S.; Xu, Z. K. Novel porphyrinated polyimide nanofibers by electrospinning. J. Phys. Chem. C, 2008, 112, 10609-10615.
37. Lv, Y. Y.; Wu, J.; Xu, Z. K.; Colorimetric and fluorescent sensor constructing from the nanofibrous membrane of porphyrinated polyimide for the detection of hydrogen chloride gas. Sensor. Actuat. B-Chem., 2010, 148, 233-239.
38. Cano, M.; Castillero, P.; Roales, J.; Pedrosa, J. M.; Brittle, S.; Richardson, T.; González-Elipe, A. R.; Barranco, A. A transparent TMPyP/TiO2 composite thin film as an HCl sensitive optochemical gas sensor. Sensor. Actuat. BChem., 2010, 150, 764-769.
39. Muthukumar, P.; John, S. A. Highly sensitive detection of HCl gas using a thin film of meso-tetra(4-pyridyl)porphyrin coated glass slide by optochemical method, Sensor. Actuat. B-Chem., 2011, 159, 238-244.
40. Peter, C.; Schmitt, K.; Apitz, M.; Woellenstein, J. Metallo-porphyrin zinc as gas sensitive material for colorimetric gas sensors on planar optical waveguides. Microsyst. Technol., 2012, 18, 925-930.
41. Kladsomboon, Su.; Kerdcharoen, T. A method for the detection of alcohol vapours based on optical sensing of magnesium 5,10,15,20-tetraphenyl porphyrin thin film by an optical spectrometer and principal component analysis. Anal. Chim. Acta, 2012, 757, 75-82.
42. Diab, N.; Schuhmann, W. Electropolymerized manganese porphyrin/polypyrrole films as catalytic surfaces for the oxidation of nitric oxide. Electrochim. Acta, 2001, 47, 265-273.
43. Bedioui, F.; Bouhier, Y.; Sorel, C.; Dewynck, J.; Guerente, L. C.; Deronzier, A.; Moutet, J. C. Incorporation of anionic metalloporphyrins into poly (pyrrole-alkylammonium) films-Part 2. Characterization of the reactivity of the iron (III) porphyrininc-based polymer. Electrochim. Acta, 1993, 38, 2485-2491.
44. Paul, S.; Amalraj, F.; Radhakrishnan, S. CO sensor based on polypyrrole functionalized with iron porphyrin. Synth. Metals, 2009, 159, 1019-1023.
45. Morales-Bahnik, A.; Czolk, R.; Ache, H. J. An optochemical ammonia sensor based on immobilized metalloporphyrins. Sens. Actuators B: Chem., 1994, 18-19, 493-496.
46. Vaughan, A. A.; Baron, M. G.; Narayanaswamy, R. Optical ammonia sensing films based on immobilized metalloporphyrin. Anal. Commun. 1996, 33, 393-396.
47. Muthukumar, P.; John, S. A. Optochemical ammonia gas sensing properties of meso-substituted porphyrin derivatives immobilized Nafion film on glass slide. Sensor. Actuat. B-Chem., 2012, 174, 74-80.
48. Duarte, J. C.; Luz, R. C.S.; Damos, F. S.; Tanak, A. A.; Kubota, L. T. A highly sensitive amperometric sensor for oxygen based on iron(II) tetrasulfonated phthalocyanine and iron(III) tetra-(N-methyl-pyridyl)-porphyrin multilayers. Anal. Chim. Acta, 2008, 612, 29-36.
49. Bennett, J. A.; Neiswonger, M. A.; Wheeler, C. D.; Pander III JE.; McKinney SE. Cyanide-coordinated Fe(III) meso-tetra(4-carboxyphenyl) porphyrin as a possible electrocatalytic material for selective H2S oxidation. J. Electrochem. Soc., 2012, 159, F119.
50. Bennett, J. A.; Wheeler, C. D.; Sterling, K. L.; Chiodo, A. M. Exploring dicyano-ferriprotoporphyrin as a novel electrocatalytic material for selective H2S gasotransmitter detection. Electrochim. Acta, 2013, 88, 86-93.
51. Xiang, H. F.; Zhou, L.; Feng, Y.; Cheng, J. H.; Wu, D.; Zhou, X. G. Tunable fluorescent/phosphorescent platinum(II) porphyrin fluorene copolymers for ratiometric dual emissive oxygen sensing. Inorg. Chem., 2012, 51, 5208-5212.
52. Tao, S. Y.; Li, G. T.; Zhu, H. S. Metalloporphyrins as sensing elements for the rapid detection of trace TNT vapor. J. Mater. Chem. 2006, 16, 4521-4528.
53. Johnson-White, B.; Zeinali, M.; Shaffer, K. M.; Patterson, C. H.; Charles, P. T.; Markowitz, M. A. Poly[meso-tetrakis(2-thienyl)porphyrin] for the sensitive electrochemical detection of explosives. Biosens. Bioelectron., 2007, 22, 1154-1162.
54. Tao, S. Y.; Li, G. T. Porphyrin-doped mesoporous silica films for rapid TNT detection. Colloid Polym. Sci., 2007, 285, 721-728.
55. Tao, S. Y.; Li, G. T.; Yin, J. X. Fluorescent nanofibrous membranes for trace detection of TNT vapor. J. Mater. Chem., 2007, 17, 2730-2736.
56. Tao, S.; Yin, J.; Li, G.High-performance TNT chemosensory materials based on nanocomposites with bimodal porous structures. J. Mater. Chem., 2008, 18, 4872-4878.
57. Chevallier, E.; Scorsonea, E.; Girarda, H.A.; Pichot, V.; Spitzer, D.; Bergonzo, P. Metalloporphyrin-functionalised diamond nano-particles as sensitive layer for nitroaromatic vapours detection at room-temperature. Sensor. Actuat. B-Chem., 2010, 151, 191-197.
58. Chen, W.; Wang, Y.; Brückner, C.; Li, C. M.; Lei, Y. Poly[meso-tetrakis(2thienyl)porphyrin] for the sensitive electrochemical detection of explosives. Sensor. Actuat. B-Chem., 2010, 147, 191-197.
59. Guo, C. X.; Lei, Y.; Li, C. M. Porphyrin functionalized graphene for sensitive electrochemical detection of ultratrace explosives. Electroanalysis, 2011, 23, 885-893.
60. Lu, X. Q.; Quan, Y. L.; Xue, Z. H.; Wu, B. W.; Qi, H. T.; Liu, D. Determination of explosives based on novel type of sensor using porphyrin functionalized carbon nanotubes. Colloid. Surface. B, 2011, 88, 396-401.
61. Ju H. NanoBiosensing: Principles, Development and Application; Biological and Medical Physics, Biomedical Engineering, Springer Science Business Media, LLC 2011, Chapter 4, pp. 111-146.
62. 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. 2009, 15, 779-784.
63. 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., 2008, 10, 766-769.
64. Wang, C.; Yuan, R.; Chai, Y. Q.; Chen, S. H.; Zhang, Y.; Hu, F. X.; Zhang, M. H. Non-covalent iron(III)-porphyrin functionalized multi-walled carbon nanotubes for the simultaneous determination of ascorbic acid, dopamine, uric acid and nitrite. Electrochim. Acta, 2012, 62, 109-115.
65. Wu, L.; Feng, L. Y.; Ren, J. S.; Qu, X. G. Electrochemical detection of dopamine using porphyrin-functionalized grapheme. Biosens. Bioelectron., 2012, 34, 57-62.
66. Pinto, S. M. A.; Lourenco, M. A. O.; Calvete, M. J. F.; Abreu, A. R.; Rosado, M. T. S.; Burrows, H. D.; Pereira, M. M. Synthesis of new metalloporphyrin triads: efficient and versatile tripod optical sensor for the detection of amines. Inorg. Chem., 2011, 50, 7916-7918.
67. Prashanthi, S.; Kumar, P. H.; Wang, L.; Perepogu, A. K.; Bangal, P. R. Reductive fluorescence quenching of the photoexcited free base meso-tetrakis (pentafluorophenyl) porphyrin by amines. J. Fluoresc., 2010, 20, 571-580.
68. Seong, D. Y.; Choi, M. S.; Kim, Y. J. Fluorescent chemosensor for the detection of histamine based on dendritic porphyrin-incorporated nanofibers. Eur. Polym. J., 2012, 48, 1988-1996.
69. Li, J.; Tu, W. W.; Lei, J. P.; Tang, S.; Ju, H. X. Porphyrin-functionalized gold nanoparticles for selective electrochemical detection of peroxyacetic acid. Electrochim. Acta, 2011, 56, 3159-3163.
70. Mazzotta, E.; Malitesta, C. Electrochemical detection of the toxic organohalide 2,4-DB using a Co-porphyrin based electrosynthesized molecularly imprinted polymer. Sensor. Actuat. B-Chem., 2010, 148, 186-194.
71. Dai, Y. X.; Zhang, N.; Wu, D.; Yang, J.; Zhao, J.; Chen, G. D.; Zhao, W.; Feng, R.; Du, B.; Wei, Q. Meso-Tetra-(3,5-dibromo-4-hydroxydroxyphenyl) porphyrin copper (II) self-assembled modified gold electrode through L- cysteine: the preparation, electrochemical behavior and its application. J. Inorg. Organomet. Polym., 2011, 21, 871-875.
72. Villari, V.; Mineo, P.; Scamporrino, E.; Micali, N. Amino acids recognition by water-soluble uncharged porphyrin tweezers: Spectroscopic evidences in high optical density solutions. Chem. Phys., 2012, 402, 118-123.
73. 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, 2008, 75,163-166.
74. D'Urso, A.; Mammana, A.; Balaz, M.; Holmes, A. E.; Berova, N.; Lauceri, R.; Purrello, R. Interactions of a tetraanionic porphyrin with DNA: from a ZDNA sensor to a versatile supramolecular device. J. Am. Chem. Soc. 2009, 131, 2046-2047.
75. D'Urso, A.; Choi, J. K.; Shabbir-Hussain, M.; Ngwa, F. N.; Lambousis, M. I.; Purrello, R.; Balaz, M. Recognition of left-handed Z-DNA of short unmodified oligonucleotides under physiological ionic strength conditions. Biochem. Biophys. Res. Commun., 2010, 397, 329-332.
76. D'Urso, A.; Holmes, A. E.; Berova, N.; Balaz, M.; Purrello, R. Z-DNA recognition in B-Z-B sequences by a cationic zinc porphyrin. Chem. Asian J. 2011, 6, 3104-3109.
77. Choi, J. K.; Sargsyan, G.; Shabbir-Hussain, M.; Holmes, A. E.; Balaz, M. Chiroptical detection of Ccondensed nickel(II)-Z-DNA in the presence of the B-DNA via porphyrin eExciton coupled circular dichroism. J. Phys. Chem. B, 2011, 115, 10182-10188.
78. Holmes, A. E.; Choi, J. K.; Francis, J.; D'Urso, A.; Balaz, M. Sulfonated Ni(II)porphyrin improves the detection of Z-DNA in condensed and noncondensed BZB DNA sequences. J. Inorg. Biochem., 2012, 110, 18-20.
79. Li, J.; Lei, J. P.; Wang, Q. B.; Wang, P.; Ju, H. X. Bionic catalysis of porphyrin for electrochemical detection of nucleic acids. Electrochim Acta, 2012, 83, 73-77.
80. Ibrahim, H.; Kasselouri, A.; Raynal, B.; Pansu, R.; Prognon, P. Investigating the possible use of a tetra(hydroxyphenyl)porphyrin as a fluorescence probe for the supramolecular detection of phospholipids. J. Luminescence, 2011, 131, 2528-2537.
81. Wu, L. N.; Lei, J. P.; Zhang, X. J.; Ju, H. X. Biofunctional nanocomposite of carbon nanofiber with water-soluble porphyrin for highly sensitive ethanol biosensing, Biosens. Bioelectron., 2008, 24, 644-649.
82. Thiagarajan, S.; Wu, Z. Y.; Chen, S. M. Amperometric determination of sodium hypochlorite at poly MnTAPP-nano Au film modified electrode. J. Electroanal. Chem., 2011, 661, 322-328.
83. Hargrove, A. E.; Reyes, R. N.; Riddington, I.; Anslyn, E. V.; Sessler, J. L. Boronic acid porphyrin receptor for ginsenoside sensing. Org. Lett., 2010, 12, 4804-4807.
84. You, M. X.; Wang, Y. X.; Wang, H.; Yang, R. H. Fluorescent detection of singlet oxygen: Amplifying signal transduction and improving sensitivity based on intramolecular FRET of anthryl appended porphyrins. Chinese Sci. Bull., 2011, 56, 3253-3259.
85. Cao, X. W.; Lin, W. Y.; Yu, Q. X. A ratiometric fluorescent probe for thiols based on a tetrakis (4-hydroxyphenyl)porphyrin coumarin scaffold. J. Org. Chem., 2011, 76, 7423-7430.