Singlet oxygen generation by cyclometalated complexes and applications

Photochemistry and Photobiology

Volumn 90, Issue 2, 2014, Pages 257-274

  Ashen Garry, David ^a   Selke, Matthias ^a  

^a CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METAL; SINGLET OXYGEN;

CHEMISTRY; CYCLIZATION;

CYCLIZATION; METALS; SINGLET OXYGEN;

EID: 84896390814     PISSN: 00318655     EISSN: 17511097     Source Type: Journal    
DOI: 10.1111/php.12211     Document Type: Review

References (89)

1. Frimer, A. A., (ed.) (1985) Singlet O2. CRC Press, Boca Raton, Fl.
2. DeRosa, M. C., and, R. J. Crutchley, (2002) Photosensitized singlet oxygen and its applications. Coord. Chem. Rev. 233, 351-371.
3. Schweitzer, C., and, R. Schmidt, (2003) Physical mechanisms of generation and deactivation of singlet oxygen. Chem. Rev. 103, 1685-1757.
4. Clennan, E. L., and, A. Pace, (2005) Advances in singlet oxygen chemistry. Tetrahedron 61, 6665-6691.
5. Wagnerová, D. M., and, K. Lang, (2011) Photorelease of triplet and singlet oxygen from dioxygen complexes. Coord. Chem. Rev. 255, 2904-2911.
6. Kessel, D., T. H. Foster, (eds.) (2007) Symposium-in-print: Photodynaminc therapy. Photochem. Photobiol. 82, 995-1282.
7. Vigant, F., J. Lee, A. Hollmann, L. B. Tanner, Z. A. Ataman, T. Yun, G. Shui, H. C. Aguilar, D. Zhang, D. Meriwether, G. Roman-Sosa, L. R. Robinson, T. L. Juelich, H. Buczkowski, S. Chou, M. A. R. B. Casanho, M. C. Wolf, J. K. Smith, A. Banyard, M. Kielan, S. Reddy, M. R. Wenk, M. Selke, N. C. Santos, A. N. Freiberg, M. E. Jung, and, B. Lee, (2013) A mechanistic paradigm for broad-Spectrum antivirals that target virus-cell fusion. PLoS Pathog. 9 (4): e1003297.
8. Lambeth, D. J., (2004) NOX enzymes and the biology of reactive oxygen. Nature Rev. Immunol. 4, 181-189.
9. Wentworth Jr., P., H. L. Jones, A. D. Wentworth, X. Zhu, N. A. Larsen, I. A. Wilson, X. Xu, W. A. Goddard III, K. J. Janda, A. Eschenmoser, and, R. A. Lerner, (2001) Antibody catalyses in the oxidation of water. Science 293, 1806-1811.
10. Schultz, P. G., J. Yin, and, R. A. Lerner, (2002) The chemistry of the antibody molecule. Angew. Chem. Int. Ed. 41, 4427-4437.
11. Aubry, J.-M., C. Pierlot, J. Rigaudy, and, R. Schmidt, (2003) Physical mechanisms of generation and deactivation of singlet oxygen. Acc. Chem. Res. 36, 668-675.
12. Turro, N. J., M.-F. Chow, and, J. Rigaudy, (1981) Mechanism of thermolyses of endoperoxides of aromatic compounds. Activation parameters, magnetic fields and magnetic isotope effects. J. Am. Chem. Soc. 103, 7218-7224.
13. Turro, N. J., (2011) Fun with photons, reactive intermediates and friends. Skating on the edge of the paradigms of physical organic chemistry, organic supramolecular photochemistry, and spin chemistry. J. Org. Chem. 76, 9863-9890.
14. Redmond, R. W., and, J. N. Gamlin, (1999) A compilation of singlet oxygen quantum yields from biologically relevant molecules. Photochem. Photobiol. 70, 391-475.
15. Lang, K., J. Mosinger, and, D. M. Wagnerová, (2004) Photophysical properties of porphyrinoid sensitizers non-covalently bound to host molecules; models for photodynamic therapy. Coord. Chem. Rev. 248, 321-350.
16. Ishii, K., (2012) Functional singlet oxygen generators based on phthalocyanines. Coord. Chem. Rev. 256, 1556-1568.
17. Awuah, S. G., and, Y. Youngjae, (2012) Boron-dipyrromethene (BODIPY)-based photosensitizers for photodynamic therapy. RSC Adv. 2, 11169-11183.
18. Kamkaev, A., S. H. Lim, H. B. Lee, L. V. Kiew, L. Y. Chung, and, K. Burgess, (2013) BODIPY dyes in photodynamic therapy. Chem. Soc. Rev. 42, 77-88.
19. Demas, J. N., E. W. Harris, and, R. P. McBride, (1977) Energy transfer from luminescent transition metal complexes to oxygen. J. Am. Chem. Soc. 99, 3547-3551.
20. Connick, W. B., and, H. B. Gray, (1997) Photooxidation of platinum(II) diimine dithiolates. J. Am. Chem. Soc. 119, 11620-11627.
21. Dungey, K. E., B. D. Thompson, N. A. P. Kane-Maguire, and, L. L. Wright, (2000) Photobehavior of (α-Diimine)dimesitylplatinum(II) complexes. Inorg. Chem. 39, 5192.
22. Abdel-Shafi, A. A., D. R. Worrall, and, A. Y. Ershov, (2004) Photosensitized generation of singlet oxygen from ruthenium(II) and osmium(II) bipyridyl complexes. Dalton Trans. 30-36.
23. Abdel-Shafi, A. A., J. L. Bourdelande, and, S. S. Ali, (2007) Photosensitized generation of singlet oxygen from rhenium(I) and iridium(III) complexes. Dalton Trans. 2510-2516.
24. 2- complex ions. Dalton Trans. 2517-1527.
25. Zhao, J., S. Ji, W. Wu, W. Wu, H. Guo, J. Sun, H. Sun, Y. Liu, Q. Li, and, L. Huang, (2012) Transition metal complexes with strong absorption and long-lived excited states: From molecular design to applications. RSC Adv. 2, 1712-1728.
26. Zhao, J., W. Wu, J. Sun, and, S. Guo, (2013) Triplet photosensitizers: From molecular design to applications. Chem. Soc. Rev. 42, 5323-5351.
27. Lowry, M. S., and, S. Bernhard, (2006) Synthetically tailored excited states: Phosphorescent, cyclometalated Iridium(III) complexes and their applications. Chem. Eur. J. 12, 7970-7977.
28. You, Y., and, W. Nam, (2012) Photofunctional triplet excited states of cyclometalated Ir(III) complexes: Beyond electroluminescence. Chem. Soc. Rev. 41, 7061-7084.
29. Forrest, S., P. Burrows, and, M. E. Thompson, (2000) The dawn of organic electronics. IEEE Spectr. 37, 29-34.
30. Holder, E., B. M. W. Lamgeveld, and, U. S. Schubert, (2002) New trends in the use of transition metal-ligand complexes for applications in electroluminescent devices. Adv. Mater. 17, 1009-1121.
31. Flamigni, L., A. Barbieri, C. Sabatini, B. Ventura, and, F. Barigelletti, (2007) Photochemistry and photophysics of coordination compounds: Iridium. Top. Curr. Chem. 281, 143-203.
32. Hay, P. J., (2002) Theoretical studies of the ground and excited electronic states in cyclometalated phenylpyridine Ir(III) complexes using density functional theory. J. Phys. Chem. C 106, 1634-1641.
33. Lamansky, S., P. Djurovich, D. Murphy, F. Abdel-Razzaq, H.-E. Lee, C. Adachi, P. E. Burrows, S. R. Forrest, and, M. E. Thompson, (2001) Highly phosphorescent bis-cyclometalated iridium complexes: Synthesis, photophysical characterization, and use in organic light emitting diodes. J. Am. Chem. Soc. 123, 4304-4312.
34. Lowry, M. S., W. R. Hudson, R. A. Pascal Jr., and, S. Bernard, (2004) Accelerated luminophore discovery through combinatorial synthesis. J. Am. Chem. Soc. 126, 14129-14135.
35. Lowry, M. S., J. I. Goldsmith, J. D. Slinker, R. Rohl, R. A. Pascal Jr., G. G. Malliaras, and, S. Bernard, (2005) Single-layer electroluminescent devices and photoinduced hydrogen production from an ionic iridium(III) complex. Chem. Mater. 17, 5712-5719.
36. Chirdon, D. N., C. E. McCusker, F. N. Castellano, and, S. Bernard, (2013) Tracking of tuning effects in bis-cyclometalated iridium complexes: A combined time resolved infrared spectroscopy, electrochemical, and computational study. Inorg. Chem. 52, 8795-8804.
37. You, Y., and, S. Y. Park, (2005) Inter ligand energy transfer and related emission change in the cyclometalated heteroleptic iridium complex: Facile and efficient color tuning over the whole visible range by the ancillary ligand structure. J. Am. Chem. Soc. 127, 12438-12439.
38. Rausch, A. F., M. E. Thompson, and, H. Yersin, (2009) Blue light emitting Ir(III) compounds for OLEDs-new insights into ancillary ligand effects on the emitting triplet state. J. Phys. Chem. A 113, 5927-5932.
39. Li, J., P. I. Djurovich, B. D. Alleyne, M. Yousofuddin, N. N. Ho, J. C. Thomas, J. C. Peters, R. Bau, and, M. E. Thompson, (2005) Synthetic control of excited-state properties in cyclometalated Ir(III) complexes using ancillary ligands. Inorg. Chem. 44, 1713-1727.
40. Sprouse, S., K. A. King, P. J. Spellane, and, R. J. Watts, (1984) Photophysical effects of metal-carbon-bonds in ortho-metallated complexes of iridium(III) and rhodium(III). J. Am. Chem. Soc. 106, 6647-6653.
41. Ohawa, Y., S. Sprouse, K. A. King, M. K. DeArmond, K. W. Hanck, and, R. J. Watts, (1987) Electrochemistry and spectroscopy of ortho-metallated complexes of Ir(III) and Rh(III). J. Phys. Chem. 91, 1047-1054.
42. Tamayo, A. B., B. D. Alleyne, P. I. Djurovich, S. Lamansky, I. Tsyba, N. N. Ho, R. Bau, and, M. E. Thompson, (2005) Synthesis and characterization of facial and meridional tris-cyclometalated complexes. J. Am. Chem. Soc. 125, 7377-7387.
43. Liu, S., P. Müller, and, M. K. Takase, and, T. M. Swager, (2011) "Click" Synthesis of Heteroleptic tris-cyclometalated iridium(III) complexes: Cu(I) triazolide intermediates as transmetalating reagents. Inorg. Chem. 50, 7598-7609.
44. Gao, R., D. G. Ho, B. Hernandez, M. Selke, D. Murphy, P. I. Djurovich, and, M. E. Thompson, (2002) Bis-cyclometalated Ir(III) complexes as efficient singlet oxygen sensitizers. J. Am. Chem. Soc. 124, 14828-14829.
45. Djurovich, P. I., D. Murphy, M. E. Thompson, B. Hernandez, R. Gao, P. L. Hunt, and, M. Selke, (2007) Cyclometalated iridium and platinum complexes as singlet oxygen photosensitizers: Quantum yields, quenching rates and correlation with electronic structures. Dalton Trans. 34, 3763-3770.
46. Gijzeman, O. L. J., F. Kaufman, and, G. Porter, (1973) Oxygen quenching by aromatic triplet states in solution. Part 1. J. Chem. Soc., Faraday Trans. 2 (69), 708-720.
47. Gijzeman, O. L. J., and, F. Kaufman, (1973) Oxygen quenching by aromatic triplet states in solution. Part 2. J. Chem. Soc., Faraday Trans. 2 (69), 721-726.
48. Bansal, A. K., W. Holzer, A. Penzkofera, and, T. Tsuboi, (2006) Absorption and emission spectroscopic characterization of platinium-octaethyl- porphyrin (PtOEP). Chem. Phys. 330, 118-129.
49. Papkovsky, D. B., and, T. C. O'Riordan, (2005) Emerging applications of posphorescent metalloporphyrins. J. Fluoresc. 15, 569-584.
50. Schaffner-Hamann, C., A. von Zelewsky, A. Barbieri, F. Barigelletti, G. Muller, J. P. Riehl, and, A. Neels, (2004) Diastereoselective formation of chiral tris-cyclometalated iridium (III) complexes: Characterization and photophysical properties. J. Am. Chem. Soc. 126, 9339.
51. Whittle, V. L., and, J. A. G. Williams, (2008) A new class of iridium complexes suitable for stepwise incorporation into linear assemblies: Synthesis, electrochemistry, and luminescence. Inorg. Chem. 47, 6596-6607.
52. Takizawa, S., R. Aboshi, and, S. Murata, (2011) Photooxidation of 1,5-dihydroxynaphthalene with iridium complexes as singlet oxygen sensitizers. Photochem. Photobiol. Sci. 10, 895-903.
53. Moromizato, S., Y. Hisamatsu, T. Suzuki, Y. Matsuo, R. Abe, and, S. Aoki, (2012) Design and synthesis of a luminescent cyclometalated iridium(III) complex having N, N-diethylamino group that stains acidic intracellular organelles and induces cell death by photoirradiation. Inorg. Chem. 51, 12697-12706.
54. Jin, J., H.-W. Shin, J. H. Park, J. H. Park, E. Kim, T. K. Ahn, D. H. Ryu, and, S. U. Son, (2013) Iridium complexes containing bis(imidazoline thione) and bis(imidazoline selone) ligands for visible-light-induced oxidative coupling of benzylamines to imines. Organometallics 32, 3954-3959.
55. Takizawa, S., J. Nishida, T. Tsuzuki, S. Tokito, and, Y. Yamashita, (2007) Phosphorescent iridium complexes based on 2-phenylimidazo[1,2-a]pyridine ligands: Tuning of emission color toward the blue region and application to polymer light-emitting devices. Inorg. Chem. 46, 4308-4319.
56. Mori, K., M. Tottori, K. Watanabe, M. Che, and, H. Yamashita, (2011) Photoinduced aerobic oxidation driven by phosphorescence Ir(III) complex anchored to mesoporous silica. J. Phys. Chem. C 115, 21358-21362.
57. Hsieh, J.-M., M.-L. Ho, P.-W. Wu, P.-T. Chou, T.-T. Tsai, and, Y. Chi, (2006) Iridium-complex modified CdSe/ZnS quantum dots; a conceptual design for bifunctionality toward imaging and photosensitization. Chem. Commun. 615-617.
58. Li, S. P.-Y., C. T.-S. Lau, M.-W. Louie, Y.-W. Lam, S. H. Cheng, and, K. K.-W. Lo, (2013) Mitochondria-targeting cyclometalated iridium(III)-PEG complexes with tunable photodynamic activity. Biomaterials 34, 7519-7532.
59. 3IL triplet excited states of coumarin fluorophores by direct cyclometallation and its application for oxygen sensing and upconversion. Dalton Trans. 40, 5953-5963.
60. Ma, L., S. Guo, J. Sun, C. Zhong, J. Zhao, and, H. Guo, (2013) Green light-excitable naphthalenediimide acetylide-containing cyclometalated Ir(III) complex with long-lived triplet excited states as triplet photosensitizers for triplet-triplet annihilation upconversion. Dalton Trans. 42, 6478-6488.
61. 60) dyads with bidirectional "ping pong" energy transfer as triplet photosensitizers for photooxidation of 1,5-dihydroxyhaphthalene. Chem. Commun. 48, 3751-3753.
62. Sun, J., J. Zhao, H. Guo, and, W. Wu, (2012) Visible-light harvesting iridium complexes as singlet oxygen sensitizers for photooxidation of 1,5-dihydroxynaphthalene. Chem. Commun. 48, 4169-4171.
63. Sun, J., F. Zhong, X. Yi, and, J. Zhao, (2013) Efficient enhancement of the visible-light absorption of cyclometalated Ir(III) complexes triplet photosensitizers with Bodipy and applications in photooxidation and triplet-triplet annihilation upconversion. Inorg. Chem. 52, 6299-6310.
64. Sun, J., F. Zhong, and, J. Zhao, (2013) Observation of the long-lived triplet excited state of perylenebisimide (PBI) in C^N cyclometalated Ir(III) complexes and application in photocatalytic oxidation. Dalton Trans. 42, 9595-9605.
65. Sajoto, T., P. I. Djurovich, A. B. Tamayo, J. Oxgaard, W. A. Goddard III, and, M. E. Thompson, (2009) Temperature dependence of blue phosphorescent cyclometalated Ir(III) complexes. J. Am. Chem. Soc. 131, 9813-9822.
66. Maestri, M., D. Sandrini, V. Balzani, L. Chassot, P. Jolliet, and, A. von Zelewsky, (1985) Luminescence of ortho-metalated platinum(II) complexes. Chem. Phys. Lett. 122, 375-379.
67. 2). J. Chem. Soc., Dalton Trans. 1645-1651.
68. Lai, S.-W., M. C. W. Chan, S.-M. Peng, and, C.-M. Che, (1999) Self-assembly of predesigned trimetallic macrocycles based on benzimidazole as non-linear bridging motifs: Crystal structure of a luminescent platinum(II) cyclic trimer. Angew. Chem. Int. Ed. 38, 669-671.
69. Lai, S.-W., M. C.-W. Chan, T.-C. Cheung, S.-M. Peng, and, C.-M. Che, (1999) Probing d8-d8 interactions in luminescent mono- and binuclear cyclometalated platinum(II) complexes of 6-phenyl-2,2′-bipyridines. Inorg. Chem. 38, 4046-4055.
70. Lai, S.-W., and, C.-M. Che, (2004) Luminescent cyclometalated diimine platinum(II) complexes: Photophysical studies and applications. Top. Curr. Chem. 241, 27-63.
71. Lu, W., B.-X. Mi, M. C. W. Chan, Z. Hui, C.-M. Che, N. Zhu, and, S.-T. Lee, (2004) Light-emitting tridentate cyclometalated platinum(II) complexes containing σ-alkynyl auxiliaries: Tuning of photo- and electrophosphorescence. J. Am. Chem. Soc. 126, 4958-4971.
72. Siu, P. K.-M., D.-L. Ma, and, C.-M. Che, (2005) Luminescent cyclometalated platinum(II) complexes with amino acid ligands for protein binding. Chem. Commun. 1025-1027.
73. Kvam, P.-I., M. V. Puzyk, V. S. Cotlyr, K. P. Balashev, and, J. Songstad, (1995) Properties of mixed-ligand cyclometalated platinum(II) complexes derived from 2-phenylpyridine and 2-(2′-thienyl)pyridine-voltammetric, absorption and emission studies. Acta Chem. Scand. 49, 645-652.
74. Zhou, C.-H., and, X. Zhao, (2011) Theoretical investigation on quinoline-based platinum (II) complexes as efficient singlet oxygen photosensitizers in photodynamic therapy. J. Organomet. Chem. 696, 3322-3327.
75. Shavaleev, N. M., H. Adams, J. Best, R. Edge, S. Navaratnam, and, J. A. Weinstein, (2006) Deep-red luminescence and efficient singlet oxygen generation by cyclometalated platinum(II) complexes with 8-hydroxyquinolines and quinoline-8-thiol. Inorg. Chem. 45, 9410-9415.
76. g) sensitization. J. Photochem. Photobiol. A: Chem. 79, 11-17.
77. Brooks, J., Y. Babayan, S. Lamansky, P. I. Djurovich, I. Tsyba, R. Bau, and, M. E. Thompson, (2002) Synthesis and characterization of phosphorescent cyclometalated platinum complexes. Inorg. Chem. 41, 3055-3066.
78. Tanielian, C., and, C. Wolff, (1988) Mechanism of physical quenching of singlet molecular oxygen by chlorophylls and related compounds of biological interest. Photochem. Photobiol. 48, 277-280.
79. Lai, S. W., Y. Liu, D. Zhang, B. Wang, C.-N. Lok, C.-M. Che, and, M. Selke, (2010) Efficient singlet oxygen generation by luminescent 2-(2′-thienyl)pyridyl cyclometalated platinum(II) complexes and their calixarene derivatives. Photochem. Photobiol. 86, 1414-1420.
80. 60. J. Phys. Chem. 95, 11-12.
81. Lai, S.-W., Q. K.-W. Chan, J. Han, Y.-G. Zhi, N. Zhu, and, C.-M. Che, (2009) Synthesis, structures and photoluminescent properties of cyclometalated platinum(II) complexes bearing upper-rim phosphinated calix[4]arenes. Organometallics 28, 34-37.
82. Wu, W., W. Wu, S. Ji, H. Guo, P. Song, K. Han, L. Chi, J. Shao, and, J. Zhao, (2010) Tuning the emission properties of cyclometalated Pt(II) complexes by intramolecular electron-sink/arylethynylated ligands and its application for enhanced luminescent oxygen sensing. J. Mat. Chem. 20, 9775-9786.
83. Wu, W., P. Yang, L. Ma, J. Lalevée, and, J. Zhao, (2013) Visible-light harvesting Pt(II) complexes as singlet oxygen photosensitizers for photooxidation of 1,5-dihydroxynaphthalene. Eur. J. Inorg. Chem. 228-231.
84. Feng, K., R.-Y. Zhang, L.-Z. Wu, B. Tu, M.-L. Peng, L.-P. Zhang, D. Zhao, and, C.-H. Tung, (2006) Photooxidation of olefins under oxygen in platinum(II) complex-loaded mesoporous molecular sieves. J. Am. Chem. Soc. 128, 14685-14690.
85. Feng, K., M.-L. Peng, D.-H. Wang, L.-P. Zhang, C.-H. Tung, and, L.-Z. Wu, (2009) Silica- and polymer-supported platinum(II) polypyridyl complexes: Synthesis and applications in photosensitized oxidation of alkenes. Dalton Trans. 44, 9794-9799.
86. Foote, C. S., (1991) Definition of type I and type II photosensitized oxidation. Photochem. Photobiol. 54, 659.
87. Jiang, G., J. Chen, J.-S. Huang, and, C.-M. Che, (2009) Highly efficient oxidation of amines to imines by singlet oxygen and its application in Ugi-type reactions. Org. Lett. 11, 4568-4571.
88. 2 core/shell nanoparticles: A facile three-in-one system in magnetic resonance imaging, luminescence imaging, and photodynamic therapy. Small 4, 218-224.
89. Demaurex, N., (2002) pH Homeostasis of cellular organelles. News Physiol. Sci. 17, 1-5.