Tridentate cyclometalated platinum(II) complexes with strong absorption of visible light and long-lived triplet excited states as photosensitizers for triplet-triplet annihilation upconversion

Dyes and Pigments

Volumn 96, Issue 1, 2013, Pages 220-231

  Wu, Wenting ^a,b   Huang, Dandan ^a   Yi, Xiuyu ^a,b   Zhao, Jianzhang ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

^b CHINA UNIVERSITY OF PETROLEUM   (China)

Author keywords

Naphthalimide; Photochemistry; Platinum; Pyrene; Triplet triplet annihilation; Upconversion

Indexed keywords

ACETYLIDE LIGANDS; ACETYLIDES; DENSITY FUNCTIONAL THEORY CALCULATIONS; FUNCTIONALIZED; LIGHT-HARVESTING; MODEL COMPLEXES; NAPHTHALIMIDE; PHOTOPHYSICAL PROPERTIES; PLATINUM COMPLEXES; PT COMPLEXES; ROOM TEMPERATURE; THEORETICAL CALCULATIONS; TIME-RESOLVED TRANSIENT ABSORPTION; TRIPLET PHOTOSENSITIZERS; TRIPLET-TRIPLET ANNIHILATION; UP-CONVERSION; VISIBLE LIGHT; VISIBLE REGION;

ABSORPTION SPECTROSCOPY; DENSITY FUNCTIONAL THEORY; EXCITED STATES; METAL COMPLEXES; PHOTOCHEMICAL REACTIONS; PHOTOSENSITIZERS; PLATINUM; PYRENE; QUANTUM YIELD; TRANSITION METAL COMPOUNDS;

PLATINUM COMPOUNDS;

EID: 84865809956     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2012.07.021     Document Type: Article

References (90)

1. C. Whittle, J.A. Weinstein, M.W. George, and K.S. Schanze Photophysics of diimine platinum(II) bis-acetylide complexes Inorg Chem 40 2001 4053 4062
2. J.E. McGarrah, Y. Kim, M. Hissler, and R. Eisenberg Toward a molecular photochemical device: a triad for photoinduced charge separation based on a platinum diimine bis(acetylide) chromophore Inorg Chem 40 2001 4510 4511
3. I.E. Pomestchenko, C.R. Luman, M. Hissler, R. Ziessel, and F.N. Castellano Room temperature phosphorescence from a platinum(II) diimine bis(pyrenylacetylide) complex Inorg Chem 42 2003 1394 1396
4. T.J. Wadas, R.J. Lachicotte, and R. Eisenberg Synthesis and characterization of platinum diimine bis(acetylide) complexes containing easily derivatizable aryl acetylide ligands Inorg Chem 42 2003 3772 3778
5. J.A.G. Williams Photochemistry and photophysics of coordination compounds: platinum Top Curr Chem 281 2007 205 268
6. J. Brooks, Y. Babayan, S. Lamansky, P.I. Djurovich, I. Tsyba, and R. Bau Synthesis and characterization of phosphorescent cyclometalated platinum complexes Inorg Chem 41 2002 3055 3066
7. W. Zhu, and L. Fan Room temperature phosphorescence of a palladium(II) complex sensitized by unsymmetric perylene bisimid Dyes Pigm 76 2008 663 668
8. J.E. McGarrah, and R. Eisenberg Dyads for photoinduced charge separation based on platinum diimine bis(acetylide) chromophores: synthesis, luminescence and transient absorption studies Inorg Chem 42 2003 4355 4365
9. S.M. Borisov, and I. Klimant Efficient metallation in diphenylether - a convenient route to luminescent platinum(II) complexes Dyes Pigm 83 2009 312 316
10. Z. Hu, Y. Wang, D. Shi, H. Tan, X. Li, and L. Wang Highly-efficiency red-emitting platinum (II) complexes containing 4′-diarylamino-1- phenylisoquinoline ligands in polymer light-emitting diodes: synthesis, structure, photoelectron and electroluminescence Dyes and Pigments 86 2010 166 173
11. F. Hua, S. Kinayyigit, J.R. Cable, and F.N. Castellano Green photoluminescence from platinum(II) complexes bearing silylacetylide ligands Inorg Chem 44 2005 471 473
12. S. Chakraborty, T.J. Wadas, H. Hester, C. Flaschenreim, R. Schmehl, and R. Eisenberg Synthesis, structure, characterization, and photophysical studies of a new platinum terpyridyl-based triad with covalently linked donor and acceptor groups Inorg Chem 44 2005 6284 6293
13. F. Guo, and W. Sun Synthesis, Photophysics and optical limiting of platinum(II) 4′-tolylterpyridyl arylacetylide complexes Inorg Chem 44 2005 4055 4065
14. B. Yin, F. Niemeyer, J.A.G. Williams, J. Jiang, A. Boucekkine, and L. Toupet Synthesis, structure, and photophysical properties of luminescent platinum(II) complexes containing cyclometalated 4-styryl-functionalized 2-phenylpyridine ligands Inorg Chem 45 2006 8584 8596
15. D.N. Kozhevnikov, V.N. Kozhevnikov, M.M. Ustinova, A. Santoro, D.W. Bruce, and B. Koenig Synthesis of cyclometallated platinum complexes with substituted thienylpyridines and detailed characterization of their luminescence properties Inorg Chem 48 2009 4179 4189
16. C.L. Ho, Q. Wang, C.S. Lam, W.Y. Wong, D. Ma, and L. Wang Phosphorescence color tuning by ligand, and substituent effects of multifunctional iridium(III) cyclometalates with 9-arylcarbazole moieties Chem Asian J 4 2009 89 103
17. G. Zhou, W.Y. Wong, S.Y. Poon, C. Ye, and Z. Lin Symmetric versus unsymmetric platinum(II) bis(aryleneethynylene)s with distinct electronic structures for optical power limiting/optical transparency trade-off optimization Adv Funct Mater 19 2009 531 544
18. W.Y. Wong, and C.L. Ho Heavy metal organometallic electrophosphors derived from multi-component chromophores Coord Chem Rev 253 2009 1709 1758
19. Q. Zhao, F. Li, and C. Huang Phosphorescent chemosensors based on heavy-metal complexes Chem Soc Rev 39 2010 3007 3030
20. R.B.P. Elmes, and T. Gunnlaugsson Luminescence anion sensing via modulation of MLCT emission from a naphthalimide-Ru(II)-polypyridyl complex Tetrahedron Letters 51 2010 4082 4087
21. R.B.P. Elmes, K.N. Orange, S.M. Cloonan, D.C. Williams, and T. Gunnlaugsson Luminescent ruthenium(II) polypyridyl functionalized gold nanoparticles; their DNA binding abilities and application as cellular imaging agents J Am Chem Soc 133 2011 15862 15865
22. W. Lu, B.X. Mi, M.C.W. Chan, Z. Hui, C.M. Che, and N. Zhu Light-emitting tridentate cyclometalated platinum(ii) complexes containing σ-alkynyl auxiliaries: tuning of photo- and electrophosphorescence J Am Chem Soc 126 2004 4958 4971
23. X. Wang, S. Goeb, Z. Ji, N.A. Pogulaichenko, and F.N. Castellano Homogeneous photocatalytic hydrogen production using π-conjugated platinum(II) arylacetylide sensitizers Inorg Chem 50 2011 705 707
24. B.F. DiSalle, and S. Bernhard Orchestrated photocatalytic water reduction using surface-adsorbing iridium photosensitizers J Am Chem Soc 133 2011 11819 11821
25. Z.M. Hudson, and S. Wang Metal-containing triarylboron compounds for optoelectronic applications Dalton Trans 40 2011 7805 7816
26. JeonYM, I.H. Lee, H.S. Lee, and M.S. Gong Orange phosphorescent organic light-emitting diodes based on spirobenzofluorene type carbazole derivatives as a host material Dyes Pigm 89 2011 29 36
27. S.O. Kim, Q. Zhao, K. Thangaraju, J.J. Kim, Y.H. Kim, and S.K. Kwon Synthesis and characterization of solution-processable highly branched iridium (III) complex cored dendrimer based on tetraphenylsilane dendron for host-free green phosphorescent organic light emitting diodes Dyes Pigm 90 2011 139 145
28. T.N. Singh-Rachford, and F.N. Castellano Photon upconversion based on sensitized triplet-triplet annihilation Coord Chem Rev 254 2010 2560 2573
29. J. Zhao, S. Ji, and H. Guo Triplet-triplet annihilation based upconversion: from triplet sensitizers and triplet acceptors to upconversion quantum yields RSC Adv 1 2011 937 950
30. P. Ceroni Energy up-conversion by low-power excitation: new applications of an old concept Chem Eur J 17 2011 9560 9564
31. M. Hissler, W.B. Connick, D.K. Geiger, J.E. McGarrah, D. Lipa, and R.J. Lachicotte Platinum diimine bis(acetylide) complexes: synthesis, characterization, and luminescence properties Inorg Chem 39 2000 447 457
32. Z. Ji, S. Li, Y. Li, and W. Sun Back-to-back dinuclear platinum terpyridyl complexes: synthesis and photophysical studies Inorg Chem 49 2010 1337 1346
33. Z. Ji, Y. Li, T.M. Pritchett, N.S. Makarov, J.E. Haley, and Z. Li One-photon photophysics and two-photon absorption of 4-[9,9-di-(2-ethylhexyl)-7- diphenylaminofluoren-2-yl]-2,2′:6′,2″-terpyridine and their platinum chloride complexes Chem Eur J 17 2011 2479 2491
34. D. Ravindranathan, D.A.K. Vezzu, L. Bartolotti, P.D. Boyle, and S. Huo Improvement in phosphorescence efficiency through tuning of coordination geometry of tridentate cyclometalated platinum(II) complexes Inorg Chem 49 2010 8922 8928
35. X. Han, L.Z. Wu, G. Si, J. Pan, Q.Z. Yang, and L.P. Zhang Switching between ligand-to-ligand charge-transfer, intraligand charge-transfer, and metal-to-ligand charge-transfer excited states in platinum(II) terpyridyl acetylide complexes induced by ph change and metal ions Chem Eur J 13 2007 1231 1239
36. P. Jarosz, K. Lotito, J. Schneider, D. Kumaresan, R. Schmehl, and R. Eisenberg Platinum(ii) terpyridyl-acetylide dyads and triads with nitrophenyl acceptors via a convenient synthesis of a boronated phenylterpyridine Inorg Chem 48 2009 2420 2428
37. W. Lu, M.C.W. Chan, N. Zhu, C.M. Che, C. Li, and Z. Hui Structural and spectroscopic studies on pt⋯pt and π-π interactions in luminescent multinuclear cyclometalated platinum(II) homologues tethered by oligophosphine auxiliaries J Am Chem Soc 126 2004 7639 7651
38. V.W.W. Yam, R.P.L. Tang, K.M.C. Wong, and K.K. Cheung Synthesis, luminescence, electrochemistry, and ion-binding studies of platinum(II) terpyridyl acetylide complexes Organometallics 20 2001 4476 4482
39. P. Du, and R. Eisenberg Energy upconversion sensitized by a platinum(II) terpyridyl acetylide complex Chem Sci 1 2010 502 506
40. II-polypyridine complex for rod-like molecular arrays J Am Chem Soc 128 2006 12616 12617
41. J. Zhao, S. Ji, W. Wu, W. Wu, H. Guo, and J. Sun Transition metal complexes with strong absorption of visible light and long-lived triplet excited states: from molecular design to applications RSC Adv 2 2011 1712 1728
42. A. Monguzzi, R. Tubino, and F. Meinardi Upconversion-induced delayed fluorescence in multicomponent organic systems: role of Dexter energy transfer Phys Rev B: Condens Matter Mater Phys 77 2008 155122/1 155122/4
43. Y.Y. Cheng, T. Khoury, R.G.C.R. Clady, M.J.Y. Tayebjee, N.J. Ekins-Daukes, and M.J. Crossley On the efficiency limit of triplet-triplet annihilation for photochemical upconversion Phys Chem Chem Phys 12 2010 66 71
44. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, and J.R. Cheeseman Gaussian 09 Revision A.1 2009 Gaussian Inc Wallingford CT
45. H. Guo, M.L. Muro-Small, S. Ji, J. Zhao, and F.N. Castellano Naphthalimide phosphorescence finally exposed in a platinum(ii) diimine complex Inorg Chem 49 2010 6802 6804
46. Y. Liu, W. Wu, J. Zhao, X. Zhang, and H. Guo Accessing the long-lived near-IR-emissive triplet excited state in naphthalenediimide with light-harvesting diimine platinum(II) bisacetylide complex and its application for upconversion Dalton Trans 40 2011 9085 9089
47. G.J. Zhao, J.Y. Liu, L.C. Zhou, and K.L. Han Site-selective photoinduced electron transfer from alcoholic solvents to the chromophore facilitated by hydrogen bonding: a new fluorescence quenching mechanism J Phys Chem B 111 2007 8940 8945
48. L. Yang, A.M. Ren, J.K. Feng, and J.F. Wang Theoretical investigation of optical and electronic property modulations of π-conjugated polymers based on the electron-rich 3,6-dimethoxy-fluorene unit J Org Chem 70 2005 3009 3020
49. 2+ sensor zinpyr-1: a computational investigation J Phys Chem A 114 2010 10427 10434
50. R.M. Edkins, A. Wriglesworth, K. Fucke, S.L. Bettingtona, and A. Beeby The synthesis and photophysics of tris-heteroleptic cyclometalated iridium complexes Dalton Trans 40 2011 9672 9678
51. L. Shi, Y. Geng, H. Gao, Z. Su, and Z. Wu Theoretical study on the electron transfer and phosphorescent properties of iridium(III) complexes with 2-phenylpyridyl and 8-hydroxyquinolate ligands Dalton Trans 39 2010 7733 7740
52. X. Li, B. Minaev, H. Ågren, and H. Tian Theoretical study of phosphorescence of Iridium complexes with fluorine-substituted phenylpyridine ligands Eur J Inorg Chem 2011 2517 2524
53. X. Gu, T. Fei, H. Zhang, H. Xu, B. Yang, and Y. Ma Tuning the emission color of Iridium(III) complexes with ancillary ligands: a combined experimental and theoretical study Eur J Inorg Chem 2009 2407 2414
54. 8 Pt-Pt interaction in a dinuclear cycloplatinated molecular "pivot-hinge" Chem Eur J 15 2009 7689 7697
55. S. Ji, W. Wu, W. Wu, P. Song, K. Han, and Z. Wang Tuning the luminescence lifetimes of Ruthenium (II) polypyridine complexes and its application in luminescent oxygen sensing J Mater Chem 20 2010 1953 1963
56. 3IL excited state as sensitizer for triplet-triplet-annihilation based upconversion Angew Chem Int Ed 50 2011 8283 8286
57. 3MLCT/3IL equilibrium: efficient triplet sensitizers for low-power upconversion Angew Chem Int Ed 50 2011 1626 1629
58. W. Wu, J. Sun, S. Ji, W. Wu, J. Zhao, and H. Guo Tuning the emissive triplet excited states of platinum(II) Schiff base complexes with pyrene, and application for luminescent oxygen sensing and triplet-triplet-annihilation based upconversions Dalton Trans 40 2011 11550 11561
59. 3IL triplet excited states of coumarin fluorophores by direct cyclometallation and its application for oxygen sensing and upconversion Dalton Trans 40 2011 5953 5963
60. H. Sun, H. Guo, W. Wu, X. Liu, and J. Zhao Coumarin phosphorescence observed with N^N Pt(II) bisacetylidecomplex and its applications for luminescent oxygen sensing and triplet-triplet-annihilation based upconversion Dalton Trans 40 2011 7834 7841
61. 3IL excited states and their application in triplet-triplet-annihilation based upconversion Eur J Inorg Chem 2011 3165 3173
62. 3IL excited state of rhodamine in a N^N pt(ii) bisacetylide complex which shows intense visible light absorption Eur J Inorg Chem 2011 4527 4533
63. 3il) of naphthalimide in cyclometalated pt(ii) complexes and its application in upconversion Inorg Chem 50 2011 11446 11460
64. A. Dreuw, and M. Head-Gordon Failure of time-dependent density functional theory for long-range charge-transfer excited states: the zincbacteriochlorin- bacteriochlorin and bacteriochlorophyl-spheroidene complexes J Am Chem Soc 126 2004 4007 4016
65. K. Hanson, A. Tamayo, V.V. Diev, M.T. Whited, P.I. Djurovich, and M.E. Thompson Efficient dipyrrin-centered phosphorescence at room temperature from bis-cyclometalated Iridium(III) dipyrrinato complexes Inorg Chem 49 2010 6077 6084
66. W. Wu, H. Guo, W. Wu, S. Ji, and J. Zhao Organic triplet sensitizer library derived from a single chromophore (bodipy) with long-lived triplet excited state for triplet-triplet annihilation based upconversion J Org Chem 76 2011 7056 7064
67. S. Guo, W. Wu, H. Guo, and J. Zhao Room-temperature long-lived triplet excited states of naphthalenediimides and their applications as organic triplet photosensitizers for photooxidation and triplet-triplet annihilation upconversions J Org Chem 77 2012 3933 3943
68. W. Wu, J. Zhao, J. Sun, and S. Guo Light-harvesting fullerene dyads as organic triplet photosensitizers for triplet-triplet annihilation upconversions J Org Chem. 77 2012 5305 5312
69. Y. Chen, J. Zhao, L. Xie, H. Guo, and Q. Li Thienyl-substituted BODIPYs with strong visible light-absorption and longlived triplet excited states as organic triplet sensitizers for triplet-triplet annihilation upconversion RSC Adv 2 2012 3942 3953
70. Y. Liu, H. Guo, and J. Zhao Ratiometric luminescent molecular oxygen sensors based on uni-luminophores of C^N Pt(II)(acac) complexes that show intense visible-light absorption and balanced fluorescence/phosphorescence dual emission Chem Commun 47 2011 11471 11473
71. II-acetylide complex with a directly metalated bodipy chromophore Chem Eur J 18 2012 1961 1968
72. M. Haase, and H. Schäfer Upconverting nanoparticles Angew Chem Int Ed 50 2011 5808 5829
73. 3+ J Phys Chem B 106 2002 10051 10057
74. 4 upconversion nanocrystals for sensitive bioimaging in vivo J Am Chem Soc 133 2011 17122 17125
75. J. Zhou, Z. Liu, and F. Li Upconversion nanophosphors for small-animal imaging Chem Soc Rev 41 2012 1323 1349
76. H.M. Kim, and B.R. Cho Two-photon probes for intracellular free metal ions, acidic vesicles and lipid rafts in live tissues Acc Chem Res 42 2009 863 872
77. T.N. Singh-Rachford, A. Nayak, M.L. Muro-Small, S. Goeb, M.J. Therien, and F.N. Castellano Supermolecular-chromophore-sensitized near-infrared-to- visible photon upconversion J Am Chem Soc 132 2010 14203 14211
78. A. Haefele, J. Blumhoff, R.S. Khnayzer, and F.N. Castellano Getting to the (square) root of the problem: how to make noncoherent pumped upconversion linear J Phys Chem Lett 3 2012 299 303
79. C. Zhang, J.Y. Zheng, Y.S. Zhao, and J. Yao Self-modulated white light outcoupling in doped organic nanowire waveguides via the fluctuations of singlet and triplet excitons during propagation Adv Mater 23 2011 1380 1384
80. V. Yakutkin, S. Aleshchenkov, S. Chernov, T. Miteva, G. Nelles, and A. Cheprakov Towards the ir limit of the triplet-triplet annihilation-supported up-conversion: tetraanthraporphyrin Chem Eur J 14 2008 9846 9850
81. Y.Y. Cheng, B. Fückel, R.W. MacQueen, Tony Khoury, R.G.C.R. Clady, and T.F. Schulze Improving the light-harvesting of amorphous silicon solar cells with photochemical upconversion Energy Environ Sci 5 2012 6953 6959
82. R.S. Khnayzer, J. Blumhoff, J.A. Harrington, A. Haefele, F. Deng, and F.N. Castellano Upconversion-powered photoelectrochemistry Chem Commun 48 2012 209 211
83. Q. Liu, T. Yang, W. Feng, and F. Li Blue-emissive upconversion nanoparticles for low-power-excited bioimaging in vivo J Am Chem Soc 134 2012 5390 5397
84. S.M. Borisov, C. Larndorfer, and I. Klimant Triplet-triplet annihilation-based anti-stokes oxygen sensing materials with a very broad dynamic range Adv Funct Mater 2012 10.1002/adfm.201200794
85. W. Wu, S. Ji, Wenting Wu, J. Shao, H. Guo, and T.D. James Ruthenium(II)-polyimine-coumarin light-harvesting molecular arrays:design rationale and application for triplet-triplet-annihilation-based upconversion Chem Eur J 18 2012 4953 4964
86. Q. Li, H. Guo, L. Ma, W. Wu, Y. Liu, and J. Zhao Tuning the photophysical properties of N^N Pt(II) bisacetylide complexes with fluorene moiety and its applications for triplet-triplet-annihilation based upconversion J Mater Chem 22 2012 5319 5329
87. S. Ji, W. Wu, J. Zhao, H. Guo, and W. Wu Efficient triplet-triplet annihilation upconversion with platinum(II) bis(arylacetylide) complexes that show long-lived triplet excited states Eur J Inorg Chem 2012 3183 3190
88. J. Sun, W. Wu, and J. Zhao Long-lived room-temperature deep-red-emissive intraligand triplet excited state of naphthalimide in cyclometalated Ir(III) complexes and its application in triplet-triplet annihilation-based upconversion Chem Eur J 18 2012 8100 8112
89. X. Yi, J. Zhao, W. Wu, D. Huang, S. Ji, and J. Sun Rhenium(I) tricarbonyl polypyridine complexes showing strong absorption of visible light and long-lived triplet excited states as a triplet photosensitizer for triplet-triplet annihilation upconversion Dalton Trans 41 2012 8931 8940
90. R.R. Islangulov, D.V. Kozlov, and F.N. Castellano Low power upconversion using MLCT sensitizers Chem Commun 2005 3776 3778