Effects of extended π-conjugation in phenanthroline (N^N) and phenylpyridine (C^N) ligands on the photophysics and reverse saturable absorption of cationic heteroleptic iridium(III) complexes

Journal of Physical Chemistry C

Volumn 118, Issue 12, 2014, Pages 6372-6384

  Li, Yuhao ^a   Dandu, Naveen ^a   Liu, Rui ^a   Li, Zhongjing ^a   Kilina, Svetlana ^a   Sun, Wenfang ^a  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; EXCITED STATES; LASER PULSES; SYNTHESIS (CHEMICAL);

2-PHENYLPYRIDINE; EXCITED STATE ABSORPTION; METAL-TO-LIGAND CHARGE TRANSFER; NANOSECOND LASER PULSE; PHOTOPHYSICAL PROPERTIES; REVERSE SATURABLE ABSORPTION; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; UV-VIS ABSORPTIONS;

LIGANDS;

EID: 84897418997     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp411259f     Document Type: Article

References (61)

1. 3IL Excited States and Their Application in Triplet-Triplet-Annihilation Based Upconversion Eur. J. Inorg. Chem. 2011, 21, 3165-3173
2. Liu, Q.; Yang, T.; Feng, W.; Li, F. Blue-Emissive Upconversion Nanoparticles for Low-Power-Excited Bioimaging in Vivo J. Am. Chem. Soc. 2012, 134, 5390-5397
3. Liu, Q.; Yin, B.; Yang, T.; Yang, Y.; Shen, Z.; Yao, P.; Li, F. A General Strategy for Biocompatible, High-Effective Upconversion Nanocapsules Based on Triplet-Triplet Annihilation J. Am. Chem. Soc. 2013, 135, 5029-5037
4. Tsuboyama, A.; Iwawaki, H.; Furugori, M.; Mukaide, T.; Kamatani, J.; Igawa, S.; Moriyama, T.; Miura, S.; Takiguchi, T.; Okada, S.; Hoshino, M.; Ueno, K. Homoleptic Cyclometalated Iridium Complexes with Highly Efficient Red Phosphorescence and Application to Organic Light-Emitting Diode J. Am. Chem. Soc. 2003, 125, 12971-12979
5. Du, B.; Lin, C.; Chi, Y.; Hung, J. Y.; Chung, M. W.; Lin, T.; Lee, G. H.; Wong, K. T.; Chou, P. T.; Hung, W. Y.; Chiu, H. C. Diphenyl(1-naphthyl) phosphine Ancillary for Assembling of Red and Orange-Emitting Ir(III) Based Phosphors; Strategic Synthesis, Photophysics, and Organic Light-Emitting Diode Fabrication Inorg. Chem. 2010, 49, 8713-8723
6. Vacca, P.; Petrosino, M.; Guerra, A.; Chierchia, R.; Minarini, C.; Della Sala, D.; Rubino, A. The Relation between the Electrical, Chemical, and Morphological Properties of Indium-Tin Oxide Layers and Double-Layer Light-Emitting Diode Performance J. Phys. Chem. C 2007, 111, 17404-17408
7. Zhao, Q.; Yu, M.; Shi, L.; Liu, S.; Li, C.; Shi, M.; Zhou, Z.; Huang, C.; Li, F. Cationic Iridium(III) Complexes with Tunable Emission Color as Phosphorescent Dyes for Live Cell Imaging Organometallics 2010, 29, 1085-1091
8. Xiong, L.; Zhao, Q.; Chen, H.; Wu, Y.; Dong, Z.; Zhou, Z.; Li, F. Phosphorescence Imaging of Homocysteine and Cysteine in Living Cells Based on a Cationic Iridium(III) Complex Inorg. Chem. 2010, 49, 6402-6408
9. Li, C.; Yu, M.; Sun, Y.; Wu, Y.; Huang, C.; Li, F. A Nonemissive Iridium(III) Complex That Specifically Lights-Up the Nuclei of Living Cells J. Am. Chem. Soc. 2011, 133, 11231-11239
10. Yoshihara, T.; Yamaguchi, Y.; Hosaka, M.; Takeuchi, T.; Tobita, S. Ratiometric Molecular Sensor for Monitoring Oxygen Levels in Living Cells Angew. Chem., Int. Ed. 2012, 51, 4148-4151
11. Zhang, S.; Hosaka, M.; Yoshihara, T.; Negishi, K.; Iida, Y.; Tobita, S.; Takeuchi, T. Phosphorescent Light-Emitting Iridium complexes Serve as a Hypoxia-Sensing Probe for Tumor Imaging in Living Animals Cancer Res. 2010, 70, 4490-4498
12. Sun, L.; Galan, A.; Ladouceur, S.; Slinker, J. D.; Zysman-Colman, E. High Stability Light-Emitting Electrochemical Cells from Cationic Iridium Complexes with Bulky 5,5′ Substituents J. Mater. Chem. 2011, 21, 18083-18088
13. Zysman-Colman, E.; Slinker, J. D.; Parker, J. B.; Malliaras, G. G.; Bernhard, S. Improved Turn-On Times of Light-Emitting Electrochemical Cells Chem. Mater. 2008, 20, 388-396
14. Bolink, H. J.; Cappelli, L.; Coronado, E.; Gratzel, M.; Orti, E.; Costa, R. D.; Viruela, P. M.; Nazeeruddin, M. K. Stable Single-Layer Light-Emitting Electrochemical Cell Using 4,7-Diphenyl-1,10-phenanthroline-bis(2- phenylpyridine)iridium(III) Hexafluorophosphate J. Am. Chem. Soc. 2006, 128, 14786-14787
15. Slinker, J. D.; Gorodetsky, A. A.; Lowry, M. S.; Wang, J. J.; Parker, S.; Rohl, R.; Bernhard, S.; Malliaras, G. G. Efficient Yellow Electroluminescence from a Single Layer of a Cyclometalated Iridium Complex J. Am. Chem. Soc. 2004, 126, 2763-2767
16. Parker, S. T.; Slinker, J. D.; Lowry, M. S.; Cox, M. P.; Bernhard, S.; Malliaras, G. G. Improved Turn-on Times of Iridium Electroluminescent Devices by Use of Ionic Liquids Chem. Mater. 2005, 17, 3187-3190
17. Zhu, M.; Zou, J.; He, X.; Yang, C.; Wu, H.; Zhong, C.; Qin, J.; Cao, Y. Triphenylamine Dendronized Iridium(III) Complexes: Robust Synthesis, Highly Efficient Nondoped Orange Electrophosphorescence and the Structure-Property Relationship Chem. Mater. 2012, 24, 174-180
18. Song, M.; Park, J. S.; Gal, Y. S.; Kang, S.; Lee, J. Y.; Lee, J. W.; Jin, S. H. Homologous Series of Phenylquinoline-Carbazole Main Ligand Based On Red-Emitting Iridium(III) Complexes for Phosphorescent Organic Light-Emitting Diodes J. Phys. Chem. C 2012, 116, 7526-7533
19. Zhao, Q.; Liu, S.; Shi, M.; Wang, C.; Yu, M.; Li, L.; Li, F.; Yi, T.; Huang, C. Series of New Cationic Iridium(III) Complexes with Tunable Emission Wavelength and Excited State Properties: Structures, Theoretical Calculations, and Photophysical and Electrochemical Properties Inorg. Chem. 2006, 45, 6152-6160
20. Kim, K. Y.; Farley, R. T.; Schanze, K. S. An Iridium(III) Complex that Exhibits Dual Mechanism Nonlinear Absorption J. Phys. Chem. B 2006, 110, 17302-17304
21. Li, Y.; Dandu, N.; Liu, R.; Hu, L.; Kilina, S.; Sun, W. Nonlinear Absorbing Cationic Iridium(III) Complexes Bearing Benzothiazolylfluorene Motif on the Bipyridine (N̂N) Ligand: Synthesis, Photophysics and Reverse Saturable Absorption ACS Appl. Mater. Interfaces 2013, 5, 6556-6570
22. He, G.; Yuan, L.; Prasad, P. N.; Abbotto, A.; Facchetti, A.; Pagani, G. A. Two-Photon Pumped Frequency-Upconversion Lasing of a New Blue-Green Dye Material Opt. Commun. 1997, 140, 49-52
23. He, G.; Xu, G.; Prasad, P. N.; Reinhardt, B. A.; Bhatt, J. C.; Dillard, A. G. Two-Photon Absorption and Optical-Limiting Properties of Novel Organic Compounds Opt. Lett. 1995, 20, 435-437
24. Denk, W.; Strickler, J. H.; Webb, W. W. Two-Photon Laser Scanning Fluorescence Microscopy Science 1990, 248, 73-76
25. Parthenopoulos, D. A.; Rentzepis, P. M. Three-Dimensional Optical Storage Memory Science 1989, 245, 843-845
26. Bhawalkar, J. D.; Kumar, N. D.; Zhao, C.; Prasad, P. N. Two-photon Photodynamic Therapy J. Clin. Med. Surg. 1997, 15, 201-204
27. Glusac, K. D.; Jiang, S. J.; Schanze, K. S. Photophysics of Ir(III) Complexes with Oligo(Arylene Ethynylene) Ligands Chem. Commun. 2002, 2504-2505
28. Zeng, X.; Tavasli, M.; Perepichka, I. F.; Batsanov, A. S.; Bryce, M. R.; Chiang, C. J.; Rothe, C.; Monkman, A. P. Cationic Bis-cyclometallated Iridium(III) Phenanthroline Complexes with Pendant Fluorenyl Substituents: Synthesis, Redox, Photophysical Properties and Light-Emitting Cells Chem.-Eur. J. 2008, 14, 933-943
29. Liu, X.; Sun, W. Synthesis and Photophysics of Platinum(II) Complexes Bearing 2-(7-(4- R -Phenylethynyl)-9,9-Dihexadecyl-Fluoren-2-yl)-1,10- Phenanthroline Ligand Inorg. Chim. Acta 2012, 388, 140-147
30. Liu, X.; Sun, W. Platinum(II) Complexes Bearing 2-(9,9-Dihexadecyl-7-R- fluoren-2-yl)-1,10-phenanthroline Ligands: Synthesis, Photophysics and Reverse Saturable Absorption Eur. J. Inorg. Chem. 2013, 27, 4732-4742
31. Dragonetti, C.; Falciola, L.; Mussini, P.; Righetto, S.; Roberto, D.; Ugo, R.; Valore, A. The Role of Substituents on Functionalized 1,10-Phenanthroline in Controlling the Emission Properties of Cationic Iridium(III) Complexes of Interest for Electroluminescent Devices Inorg. Chem. 2007, 46, 8533-8547
32. Jo, J.; Chi, C.; Hoger, S.; Wegner, G.; Yoon, D. Y. Synthesis and Characterization of Monodisperse Oligofluorenes Chem.-Eur. J. 2004, 10, 2681-2688
33. Dietrich-Buchecker, C.; Jimenez, M. C.; Sauvage, J. P. Selective and Efficient Synthesis of Di-, Tri- and Tetrasubstituted 1,10-Phenanthrolines Tetrahedron Lett. 1999, 40, 3395-3396
34. Liu, S.; Zhao, Q.; Chen, R.; Deng, Y.; Fan, Q.; Li, F.; Wang, L.; Huang, C.; Huang, W. π-Conjugated Chelating Polymers with Charged Iridium Complexes in the Backbones: Synthesis, Characterization, Energy Transfer, and Electrochemical Properties Chem.-Eur. J. 2006, 12, 4351-4361
35. Li, Y.; Liu, R.; Badaeva, E.; Kilina, S.; Sun, W. Long-Lived π-Shape Platinum(II) Diimine Complexes Bearing 7-Benzothiazolylfluoren-2-yl Motif on the Bipyridine and Acetylide Ligands: Admixing π,π* and Charge-Transfer Configurations J. Phys. Chem. C 2013, 117, 5908-5918
36. Demas, J. N.; Crosby, G. A. The Measurement of Photoluminescence Quantum Yields. A Review J. Phys. Chem. 1971, 75, 991-1024
37. Van Houten, J.; Watts, R. J. Temperature Dependence of the Photophysical and Photochemical Properties of the Tris(2,2′-bipyridyl)ruthenium(II) Ion in Aqueous Solution J. Am. Chem. Soc. 1976, 98, 4853-4858
38. Carmichael, I.; Hug, G. L. Triplet-Triplet Absorption Spectra of Organic Molecules in Condensed Phases J. Phys. Chem. Ref. Data 1986, 15, 1-250
39. Kumar, C. V.; Qin, L.; Das, P. K. Aromatic thioketone triplets and their quenching behaviour towards oxygen and di-t-butylnitroxy radical. A laser-flash-photolysis study J. Chem. Soc., Faraday Trans. 2 1984, 80, 783-793
40. Firey, P. A.; Ford, W. E.; Sounik, J. R.; Kenney, M. E.; Rodgers, M. A. J. Silicon Naphthalocyanine Triplet State and Oxygen: A Reversible Energy-Transfer Reaction J. Am. Chem. Soc. 1988, 110, 7626-7630
41. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; et al. Gaussian 09, revision A.1; Gaussian, Inc.: Wallingford, CT, 2009.
42. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868
43. Adamo, C.; Barone, V. Toward Reliable Density Functional Methods Without Adjustable Parameters: The PBE0 model J. Chem. Phys. 1999, 110, 6158-6170
44. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. A Basis Set for Correlated Wave Functions J. Chem. Phys. 1980, 72, 650-654
45. Hariharan, P. C.; Pople, J. A. The Influence of Polarization Functions on Molecular Orbital Hydrogenation Energies Theor. Chim. Acta 1973, 28, 213-222
46. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. Efficient Diffuse Function-augmented Basis Sets for Anion Calculations. III. The 3-21+G Basis Set for First-row Elements, Li-F J. Comput. Chem. 1983, 4, 294-301
47. Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. Self-consistent Molecular Orbital Methods. XXIII. A Polarization-type Basis Set for Second-row Elements J. Chem. Phys. 1982, 77, 3654-3665
48. Gill, P. M. W.; Johnson, B. G.; Pople, J. A.; Frisch, M. J. The Performance of the Becke-Lee-Yang-Parr (B-LYP) Density Functional Theory with Various Basis Sets Chem. Phys. Lett. 1992, 197, 499-505
49. Hay, P. J.; Wadt, W. R. Ab Initio Effective Core Potentials for Molecular Calculations. Potentials for K to Au Including the Outermost Core Orbitals J. Chem. Phys. 1985, 82, 299-310
50. Barone, V.; Cossi, M.; Tomasi, J. Geometry Optimization of Molecular Structures in Solution by the Polarizable Continuum Model J. Comput. Chem. 1998, 19, 404-417
51. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. Energies, Structures, and Electronic Properties of Molecules in Solution with the C-PCM Solvation Model J. Comput. Chem. 2003, 24, 669-681
52. Scalmani, G.; Frisch, M. J.; Mennucci, B.; Tomasi, J.; Cammi, R.; Barone, V. Geometries and Properties of Excited States in the Gas Phase and in Solution: Theory and Application of a Time-dependent Density Functional Theory Polarizable Continuum Model J. Chem. Phys. 2006, 124, 094107-1-094107-15
53. Furche, F.; Ahlrichs, R. Time-dependent Density Functional Methods for Excited State Properties J. Chem. Phys. 2002, 117, 7433-7447
54. Martin, R. L. Natural Transition Orbitals J. Chem. Phys. 2003, 118, 4775-4777
55. Nonoyama, M. Benzo[ h ]quinolin-10-yl- N Iridium(III) Complexes Bull. Chem. Soc. Jpn. 1974, 47, 767-768
56. + with Triple Phosphorescence J. Phys. Chem. A 2010, 114, 10339-10344
57. Tao, J.; Tretiak, S.; Zhu, J.-X. Prediction of Excitation Energies for Conjugated Oligomers and Polymers from Time-Dependent Density Functional Theory Materials 2010, 3, 3430-3467
58. Igumenshchev, K. I.; Tretiak, S.; Chernyak, V. Y. Excitonic Effects in a Time-dependent Density Functional Theory J. Chem. Phys. 2007, 127, 114902
59. El-Sayed, M. A. Spin-Orbit Coupling and the Radiationless Processes in Nitrogen Heterocyclics J. Chem. Phys. 1963, 38, 2834-2838
60. Li, Y.; Dandu, N.; Liu, R.; Kilina, S.; Sun, W. Synthesis and Photophysics of Reverse Saturable Absorbing Heteroleptic Iridium(III) Complexes Bearing 2-(7-R-Fluoren-2′-yl)pyridine Ligands Dalton Trans. 2014, 43, 1724-1735
61. Sun, W.; Zhang, B.; Li, Y.; Pritchett, T. M.; Li, Z.; Haley, J. E. Broadband Nonlinear Absorbing Platinum 2,2′-Bipyridine Complex Bearing 2-(Benzothiazol-2′-yl)-9,9-diethyl-7-ethynylfluorene Ligands Chem. Mater. 2010, 22, 6384-6392