Citation: SHEN Wei, TIAN Wen-Wen, QI Zheng-Jian, SUN Yue-Ming. Photoelectric Properties of Novel Amide-Functionalized Ir(III) Complexes[J]. Acta Physico-Chimica Sinica, ;2015, 31(11): 2174-2182. doi: 10.3866/PKU.WHXB201510084 shu

Photoelectric Properties of Novel Amide-Functionalized Ir(III) Complexes

1.
College of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, P. R. China

Corresponding author: QI Zheng-Jian, SUN Yue-Ming,
Received Date: 24 August 2015
Available Online: 8 October 2015
Fund Project: 国家重点基础研究发展规划项目(973) (2013CB932902) (973) (2013CB932902) 国家自然科学基金(21173042) (21173042) 江苏省科技支撑计划(工业)项目(BE2013118) (工业)项目(BE2013118) 江苏省科技成果转化专项资金(BA2014123) (BA2014123)国家重大科学仪器设备开发专项(2014YQ060773)资助 (2014YQ060773)

A series of luminescent cyclometalated Ir(III) complexes functionalized with amide derivatives were prepared and compared with [Ir(ppy)₂phen-NH₂]Cl. The complexes were [Ir(ppy)₂phen-Br]Cl, [Ir(ppy)₂phen-COOH]Cl, and [Ir(ppy)₂phen-Si]Cl, where ppy is 2-phenylpyridine, phen-NH₂ is 5-amino-[1,10]-phenanthroline, phen-Br is 2-bromo-2-methyl-N-(1,10-phenanthrolin-5-yl)propanamide, phen-COOH is 4-[(1,10-phenanthrolin-5-yl)amino]-4-oxobut-2-enoic acid, and phen-Si is 5-[N,N-bis-3-(triethoxysilyl) propyl]ureyl-1,10-phenanthroline. They were characterized using nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), ultraviolet-visible (UV-Vis) absorption spectroscopy, photoluminescence (PL) spectroscopy, and cyclic voltammetry (CV). The three novel complexes have intense absorptions in the blue-purple region. The complexes show bright yellow to orange PL emissions under UV irradiation, and the quantum yields (Φ) of these complexes are higher than 12%. The excited-state lifetimes of the novel complexes are 9.18-12.00 μs, much longer than that of [Ir(ppy)₂phen-NH₂]Cl (5.78 μs). With both the highest quantum yield (32%) and longest lifetime (12.00 μs), [Ir(ppy)₂phen-Br]Cl also shows the best oxygen-sensing properties and the largest I₀/I factor, 10.91 (I₀: the PL intensity of the complex in the absence of O₂, I: the PL intensity of the complex under pure oxygen). These results suggest that [Ir(ppy)₂phen-Br]Cl may be a promising candidate for use in oxygen sensors based on covalent grafting. Time-dependent density functional theory (TD-DFT) calculations were used to supplement the photoelectric property studies. Theoretical calculations indicate that all the mononuclear complexes have approximately octahedral structures with Ir(III) as the coordination center. The computational results agree well with the experimental data.
- Photoelectric property,
- Ir(III) complex,
- Phenanthroline,
- Oxygen quenching,
- Luminescence sensor
1. [1]
  (1) Zelelow, B.; Khalil, G. E.; Phelan, G.; Carlson, B.; Gouterman, M.; Callis, J. B.; Dalton, L. R. Sensor Actuat. B-Chem. 2003, 96, 304. doi: 10.1016/S0925-4005(03)00547-1
2. [2]
  (2) Borisov, S. M.; Vasylevska, A. S.; Krause, C.; Wolfbeis, O. S. Adv. Funct. Mater. 2006, 16, 1536. doi: 10.1002/adfm.200500778
3. [3]
  (3) Borisov, S. M.; Wolfbeis, O. S. Anal. Chem. 2006, 78, 5094. doi: 10.1021/Ac060311d
4. [4]
  (4) Kose, M. E.; Carroll, B. F.; Schanze, K. S. Langmuir 2005, 21, 9121. doi: 10.1021/La050997p
5. [5]
  (5) Lupo, F.; Fragala, M. E.; Gupta, T.; Mamo, A.; Aureliano, A.; Bettinelli, M.; Speghini, A.; Gulino, A. J. Phys. Chem. C 2010, 114, 13459. doi: 10.1021/Jp1028917
6. [6]
  (6) Schroder, C. R.; Polerecky, L.; Klimant, I. Anal. Chem. 2007, 79, 60. doi: 10.1021/Ac0606047
7. [7]
  (7) Borisov, S. M.; Krause, C.; Arain, S.; Wolfbeis, O. S. Adv. Mater. 2006, 18, 1511. doi: 10.1002/adma.200600120
8. [8]
  (8) Lo, K. K. W.; Li, S. P. Y.; Zhang, K. Y. New J. Chem. 2011, 35, 265. doi: 10.1039/C0nj00478b
9. [9]
  (9) Zhang, S. J.; Hosaka, M.; Yoshihara, T.; Negishi, K.; Iida, Y.; Tobita, S.; Takeuchi, T. Cancer Res. 2010, 70, 4490. doi: 10.1158/0008-5472.Can-09-3948
10. [10]
  (10) Williams, J. A. Chem. Soc. Rev. 2009, 38, 1783. doi: 10.1039/b804434c
11. [11]
  (11) Dixon, I. M.; Collin, J. P.; Sauvage, J. P.; Flamigni, L.; Encinas, S.; Barigelletti, F. Chem. Soc. Rev. 2000, 29, 385. doi: 10.1039/B000704h
12. [12]
  (12) Ulbricht, C.; Beyer, B.; Friebe, C.; Winter, A.; Schubert, U. S. Adv. Mater. 2009, 21, 4418. doi: 10.1002/adma.200803537
13. [13]
  (13) Whittle, V. L.; Williams, J. A. Dalton Trans. 2009, 3929. doi: 10.1039/b821161b
14. [14]
  (14) You, Y.; Park, S. Y. Dalton Trans. 2009, 1267. doi: 10.1039/b812281d
15. [15]
  (15) Fernandez-Moreira, V.; Thorp-Greenwood, F. L.; Coogan, M. P. Chem Commun (Camb). 2010, 46, 186. doi: 10.1039/b917757d
16. [16]
  (16) Zhao, Q.; Li, F.; Huang, C. Chem. Soc. Rev. 2010, 39, 3007. doi: 10.1039/b915340c
17. [17]
  (17) Lo, K. K. W.; Louie, M. W.; Zhang, K. Y. Coordin. Chem. Rev. 2010, 254, 2603. doi: 10.1016/j.ccr.2010.01.014
18. [18]
  (18) Lo, K. K. W. Photophysics of Organometallics 2010, 29, 115. doi: 10.1007/3418_2009_3
19. [19]
  (19) Chi, Y.; Chou, P. T. Chem. Soc. Rev. 2010, 39, 638. doi: 10.1039/b916237b
20. [20]
  (20) Yue, Y.; Xu, H. X.; Hao, Y. Y.; Xie, X. D.; Qu, L. T.; Wang, H.; Xu, B. S. Acta Phys. -Chim. Sin. 2012, 28, 1593. [岳岩, 许慧侠, 郝玉英, 解晓东, 屈丽桃, 王华, 许并社. 物理化学学报, 2012, 28, 1593.] doi: 10.3866/PKU.WHXB201204181
21. [21]
  (21) Wei, C. D.; Ge, G. P.; Li, C. Y.; Lei, K. W.; Liang, H. Z.; Yu, G.; Liu, Z. W. Acta Phys. -Chim. Sin. 2015, 31, 17. [韦传东, 葛国平, 李春艳, 雷克微, 梁洪泽, 禹钢, 刘志伟. 物理化学学报, 2015, 31, 17.] doi: 10.3866/PKU.WHXB201411212
22. [22]
  (22) Wang, L. X.; Mei, Q. B.; Yan, F.; Tian, B.; Weng, J. N.; Zhang, B.; Huang, W. Acta Phys. -Chim. Sin. 2012, 28, 1556. [王玲霞, 梅群波, 颜芳, 田波, 翁洁娜, 张彬, 黄维. 物理化学学报, 2012, 28, 1556.] doi: 10.3866/PKU.WHXB201205043
23. [23]
  (23) Ren, J. K.; Xu, H. X.; Qu, L. T.; Hao, Y. Y.; Wang, H.; Xu, B. S. Acta Phys. -Chim. Sin. 2013, 29, 1115. [任静琨, 许慧侠, 屈丽桃, 郝玉英, 王华, 许并社. 物理化学学报, 2013, 29, 1115.] doi: 10.3866/PKU.WHXB201302253
24. [24]
  (24) DeRosa, M. C.; Mosher, P. J.; Yap, G. P. A.; Focsaneanu, K. S.; Crutchley, R. J.; Evans, C. E. B. Inorg. Chem. 2003, 42, 4864. doi: 10.1021/Ic026230r
25. [25]
  (25) Huynh, L.; Wang, Z. U.; Yang, J.; Stoeva, V.; Lough, A.; Manners, I.; Winnik, M. A. Chem. Mater. 2005, 17, 4765. doi: 10.1021/cm047794r
26. [26]
  (26) Ohsawa, Y.; Sprouse, S.; King, K. A.; Dearmond, M. K.; Hanck, K. W.; Watts, R. J. J. Phys. Chem. 1987, 91, 1047. doi: 10.1021/J100289a009
27. [27]
  (27) Lowry, M. S.; Hudson, W. R.; Pascal, R. A.; Bernhard, S. J. Am. Chem. Soc. 2004, 126, 14129. doi: 10.1021/Ja047156+
28. [28]
  (28) Medina-Castillo, A. L.; Fernandez-Sanchez, J. F.; Klein, C.; Nazeeruddin, M. K.; Segura-Carretero, A.; Fernandez-Gutierrez, A.; Grä tzel, M.; Spichiger-Keller, U. E. Analyst 2007, 132, 929. doi: 10.1039/b702628e
29. [29]
  (29) Habibagahi, A.; Mebarki, Y.; Sultan, Y.; Yap, G. P.; Crutchley, R. J. ACS Appl. Mater. Interfaces 2009, 1, 1785. doi: 10.1021/am900306a
30. [30]
  (30) Di Marco, G.; Lanza, M.; Mamo, A.; Stefio, I.; Di Pietro, C.; Romeo, G.; Campagna, S. Anal. Chem. 1998, 70, 5019. doi: 10.1021/ac980234p
31. [31]
  (31) Xu, W. Y.; Ma, W. T.; Li, K. Y.; Hu, J. M.; Shen, L. R.; Li, H. Y.; Cao, L. X. Sensor Actuat. B-Chem. 2002, 86, 174. doi: 10.1016/s0925-4005(02)00165-x
32. [32]
  (32) Lu, X.; Manners, I.; Winnik, M. A. Macromolecules 2001, 34, 1917. doi: 10.1021/Ma001454j
33. [33]
  (33) Hocker, G. B. Appl. Opt. 1979, 18, 1445. doi: 10.1364/Ao.18.001445
34. [34]
  (34) Klimant, I.; Wolfbeis, O. S. Anal. Chem. 1995, 67, 3160. doi: 10.1021/Ac00114a010
35. [35]
  (35) Wang, H. Y.; Xu, G. B.; Dong, S. J. Analyst 2001, 126, 1095. doi: 10.1039/b100376n
36. [36]
  (36) Hubner, J. P.; Carroll, B. F.; Schanze, K. S.; Ji, H. F. Exp. Fluids 2000, 28, 21. doi: 10.1007/s003480050003
37. [37]
  (37) Tang, Y.; Tehan, E. C.; Tao, Z. Y.; Bright, F. V. Anal. Chem. 2003, 75, 2407. doi: 10.1021/Ac030087h
38. [38]
  (38) Bedlek-Anslow, J. M.; Hubner, J. P.; Carroll, B. F.; Schanze, K. S. Langmuir 2000, 16, 9137. doi: 10.1021/La0011679
39. [39]
  (39) Lu, X.; Winnik, M. A. Chem. Mater. 2001, 13, 3449. doi: 10.1021/Cm011029k
40. [40]
  (40) Li, H. R.; Lin, J.; Zhang, H. J.; Li, H. C.; Fu, L. S.; Meng, Q. G. Chem. Commun. 2001, 1212. doi: 10.1039/b102160p
41. [41]
  (41) Xavier, M. P.; Garcia-Fresnadillo, D.; Moreno-Bondi, M. C.; Orellana, G. Anal. Chem. 1998, 70, 5184. doi: 10.1021/Ac980722x
42. [42]
  (42) Wang, Z.; McWilliams, A. R.; Evans, C. E. B.; Lu, X.; Chung, S.; Winnik, M. A.; Manners, I. Adv. Funct. Mater. 2002, 12, 415. doi: 10.1002/1616-3028(20020618)12:6/7< 415::Aid-Adfm415> 3.0.Co; 2-Y
43. [43]
  (43) Franville, A. C.; Mahiou, R.; Zambon, D.; Cousseins, J. C. Solid State Sci. 2001, 3, 211. doi: 10.1016/S1293-2558(00)01114-6
44. [44]
  (44) Sprouse, S.; King, K. A.; Spellane, P. J.; Watts, R. J. J. Am. Chem. Soc. 1984, 106, 6647. doi: 10.1021/Ja00334a031
45. [45]
  (45) dos Santos, C. M. G.; Gunnlaugsson, T. Supramol. Chem. 2009, 21, 173. doi: 10.1080/10610270802588285
46. [46]
  (46) Reetz, M. T.; Rentzsch, M.; Pletsch, A.; Taglieber, A.; Hollmann, F.; Mondiere, R. J. G.; Dickmann, N.; Hocker, B.; Cerrone, S.; Haeger, M. C.; Sterner, R. ChemBioChem 2008, 9, 552. doi: 10.1002/cbic.200700413
47. [47]
  (47) Lee, S. J.; Bae, D. R.; Han, W. S.; Lee, S. S.; Jung, J. H. Eur. J. Inorg. Chem. 2008, 2008, 1559. doi: 10.1002/ejic.200701073
48. [48]
  (48) Lo, K. K. W.; Ng, D. C. M.; Chung, C. K. Organometallics 2001, 20, 4999. doi: 10.1021/Om010652b
49. [49]
  (49) Li, H. R.; Lin, J.; Zhang, H. J.; Fu, L. S.; Meng, Q. G.; Wang, S. B. Chem. Mater. 2002, 14, 3651. doi: 10.1021/Cm0116830
50. [50]
  (50) Okutsu, T.; Ishihara, A.; Kounose, N.; Suzuki, H. H. T.; Ichimura, T.; Hiratsuka, H. J. Photochem. Photobiol. A 2007, 186, 229. doi: 10.1016/j.jphotochem.2006.08.019
51. [51]
  (51) Sun, Y.; Liang, X. H.; Zhao, Y. Y.; Fan, J. Spectrochim. Acta A 2013, 102, 194. doi: 10.1016/j.saa.2012.10.013
52. [52]
  (52) Rodríguez-Romero, J.; Aparicio-Ixta, L.; Rodríguez, M.; Ramos-Ortíz, G.; Maldonado, J. L.; Jiménez-Sánchez, A.; Farfán, N.; Santillan, R. Dyes Pigments 2013, 98, 31. doi: 10.1016/j.dyepig. 2012.12.029
53. [53]
  (53) Malins, C.; Glever, H. G.; MacCraith, B. D.; Fanni, S.; Vos, J. G. Anal. Commun. 1999, 36, 3. doi: 10.1039/a808731h
54. [54]
  (54) Tang, L.; Qi, Z. J.; Hong, M. X.; Li, N.; Wei, S.; Yang, F.; Ji, X.; Hu, A. J. Acta Chim. Sin. 2012, 70, 1081. [唐兰兰, 祁争健, 洪满心, 李楠, 沈伟, 杨帆, 吉昕, 胡爱江. 化学学报, 2012, 70, 1081.] doi: 10.6023/A1112121
55. [55]
  (55) Wang, J. X.; Xia, H. Y.; Liu, W. Q.; Zhao, F.; Wang, Y. B. Inorg. Chim. Acta 2013, 394, 92. doi: 10.1016/j.ica.2012.07.032
56. [56]
  (56) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; et al. Gaussian 03, Revision B.05; Gaussian Inc.; Pittsburgh, PA, 2003.
1. [1]
  Zhongxin YU , Wei SONG , Yang LIU , Yuxue DING , Fanhao MENG , Shuju WANG , Lixin YOU . Fluorescence sensing on chlortetracycline of a Zn-coordination polymer based on mixed ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2415-2421. doi: 10.11862/CJIC.20240304
2. [2]
  Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
3. [3]
  Yongzhi LI , Han ZHANG , Gangding WANG , Yanwei SUI , Lei HOU , Yaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307
4. [4]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
5. [5]
  Qiaowen CHANG , Ke ZHANG , Guangying HUANG , Nuonan LI , Weiping LIU , Fuquan BAI , Caixian YAN , Yangyang FENG , Chuan ZUO . Syntheses, structures, and photo-physical properties of iridium phosphorescent complexes with phenylpyridine derivatives bearing different substituting groups. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 235-244. doi: 10.11862/CJIC.20240311
6. [6]
  Jinfeng Chu , Yicheng Wang , Ji Qi , Yulin Liu , Yan Li , Lan Jin , Lei He , Yufei Song . Comprehensive Chemical Experiment Design: Convenient Preparation and Characterization of an Oxygen-Bridged Trinuclear Iron(III) Complex. University Chemistry, 2024, 39(7): 299-306. doi: 10.3866/PKU.DXHX202310105
7. [7]
  Pengcheng Yan , Peng Wang , Jing Huang , Zhao Mo , Li Xu , Yun Chen , Yu Zhang , Zhichong Qi , Hui Xu , Henan Li . Engineering Multiple Optimization Strategy on Bismuth Oxyhalide Photoactive Materials for Efficient Photoelectrochemical Applications. Acta Physico-Chimica Sinica, 2025, 41(2): 100014-. doi: 10.3866/PKU.WHXB202309047
8. [8]
  Xingchao Zhao , Xiaoming Li , Ming Liu , Zijin Zhao , Kaixuan Yang , Pengtian Liu , Haolan Zhang , Jintai Li , Xiaoling Ma , Qi Yao , Yanming Sun , Fujun Zhang . 倍增型全聚合物光电探测器及其在光电容积描记传感器上的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2311021-. doi: 10.3866/PKU.WHXB202311021
9. [9]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
10. [10]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
11. [11]
  Yueyue WEI , Xuehua SUN , Hongmei CHAI , Wanqiao BAI , Yixia REN , Loujun GAO , Gangqiang ZHANG , Jun ZHANG . Two Ln-Co (Ln=Eu, Sm) metal-organic frameworks: Structures, magnetism, and fluorescent sensing sulfasalazine and glutaraldehyde. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2475-2485. doi: 10.11862/CJIC.20240193
12. [12]
  Jing REN , Ruikui YAN , Xiaoli CHEN , Huali CUI , Hua YANG , Jijiang WANG . Synthesis and fluorescence sensing of a highly sensitive and multi-response cadmium coordination polymer. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 574-586. doi: 10.11862/CJIC.20240287
13. [13]
  Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
14. [14]
  Xin Han , Zhihao Cheng , Jinfeng Zhang , Jie Liu , Cheng Zhong , Wenbin Hu . Design of Amorphous High-Entropy FeCoCrMnBS (Oxy) Hydroxides for Boosting Oxygen Evolution Reaction. Acta Physico-Chimica Sinica, 2025, 41(4): 100033-. doi: 10.3866/PKU.WHXB202404023
15. [15]
  Keweiyang Zhang , Zihan Fan , Liyuan Xiao , Haitao Long , Jing Jing . Unveiling Crystal Field Theory: Preparation, Characterization, and Performance Assessment of Nickel Macrocyclic Complexes. University Chemistry, 2024, 39(5): 163-171. doi: 10.3866/PKU.DXHX202310084
16. [16]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
17. [17]
  Meiqing Yang , Lu Wang , Haozi Lu , Yaocheng Yang , Song Liu . Recent Advances of Functional Nanomaterials for Screen-Printed Photoelectrochemical Biosensors. Acta Physico-Chimica Sinica, 2025, 41(2): 100018-. doi: 10.3866/PKU.WHXB202310046
18. [18]
  Yan ZHAO , Xiaokang JIANG , Zhonghui LI , Jiaxu WANG , Hengwei ZHOU , Hai GUO . Preparation and fluorescence properties of Eu³⁺-doped CaLaGaO₄ red-emitting phosphors. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1861-1868. doi: 10.11862/CJIC.20240242
19. [19]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
20. [20]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114

Get Citation

PDF

XML

Metrics

PDF Downloads(31)
Abstract views(1661)
HTML views(206)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142