Citation: LING Huan-Huan, LI Nan, YANG Fan, JI Xin, XIA Yong, CAO Du, QI Zheng-Jian. Photoelectric Properties of Novel Substituted 2-Phenyl-1H-imidazole[4,5-f][1,10]phenanthrene Ruthenium(II) Complexes[J]. Acta Physico-Chimica Sinica, ;2013, 29(11): 2465-2474. doi: 10.3866/PKU.WHXB201310085 shu

Photoelectric Properties of Novel Substituted 2-Phenyl-1H-imidazole[4,5-f][1,10]phenanthrene Ruthenium(II) Complexes

  • Received Date: 29 July 2013
    Available Online: 8 October 2013

    Fund Project: 国家自然科学基金(21075015) (21075015)江苏省科技支撑项目(BE2012810)资助 (BE2012810)

  • To obtain novel complexes with active grafting ability and high fluorescent sensing performance, four phenanthroline ligands 2-(4-aminophenyl)-1H-imidazole[4,5-f][1,10]phenanthrene (CImPB-NH2), 2-(4-hydroxyphenyl)-1H-imidazole[4,5-f][1,10]phenanthrene (CImPB-OH), 2-(4-carboxylphenyl)-1H-imidazole[4, 5-f][1,10]phenanthrene (CImPB-COOH), and 2-(4-nitrophenyl)-1H-imidazole[4,5-f][1,10]phenanthrene (CImPB-NO2) and theirruthenium(II) complexes were synthesized. The photoelectric properties of the four complexes were evaluated with UV-Vis absorption measurements, fluorescence spectrometry, cyclic voltammetry, and time-dependent density functional theory (TD-DFT) calculations. UV-Vis and photoluminescence (PL) spectroscopy results show that the four complexes have broad, strong absorption in the visible light region, and display bright luminescence, exhibiting colors from green to red. In N,N-dimethylformamide (DMF) solution, compared with that of [Ru(phen-NH2)(bpy)2]2+ which has no phenylimidazole group, the fluorescence quantum yield of the [Ru(CImPB-NH2) (bpy)2]2+ is increased by about 67% and that of [Ru(CImPB-COOH)(bpy)2]2+ is enhanced 18 times to 29.8%, emitting bright red light from 600 to 620 nm. Calculation results indicate that an extending conjugated π system is formed along the whole ligand molecular skeleton among the aromaticities of benzene, imidazole and phenanthrene, the effective conjugation length of which is increased significantly compared with the single phenanthrene ligand, and a approximate octahedral configuration is built between Ru and the functional phenanthrene ligand. All the data indicate that the results of the theoretical calculations are in od agreement with the experimental results. These investigations might provide valuable data for designing grafting and fluorescent sensors with high performance.

  • 加载中
    1. [1]

      (1) Walters, K.; Guillerez, A. L. S.; Schanze, K. S. Inorg. Chem.2000, 39, 549.

    2. [2]

      (2) Liu, C. G.; Guan,W.; Yan, L. K.; Su, Z. M.; Song, P.;Wang, E.B. J. Phys. Chem. C 2009, 113, 19672. doi: 10.1021/jp906979z

    3. [3]

      (3) Cheng, F. X.; Tang, N.; Chen, J. S.; Chen, G. Spectrochim. Acta, Part A-Mol. Biol. Spectrosc. 2013, 114, 159. doi: 10.1016/j.saa.2013.05.059

    4. [4]

      (4) Xie, Y.; Xing, Y. H.;Wang, Z.; Zhao, H. Y.; Zeng, X. Q.; Ge, M.F.; Niu, S. Y. Inorg. Chem. Commun. 2009, 12, 975. doi: 10.1016/j.inoche.2009.07.025

    5. [5]

      (5) Zhang, S. X.; Gu, Z. R.; Li, F. B.; Liu, L.; Fu, Q. M.; Liu, S. Z.;Du, Z. L.;Wong,W. Y. J. Inorg. Organomet. Polym. 2013, 23,95. doi: 10.1007/s10904-012-9745-1

    6. [6]

      (6) Henthorn, J. D.; Mishra, N.; Haun, C. D.; Castro, A. L.;Douglas, H. G.; Pegram, M.; Stadelmaier, B.; Huebner, J. S.;Lampropoulos, C. Polyhedron 2013, 53, 62. doi: 10.1016/j.poly.2013.01.017

    7. [7]

      (7) Niu, Y. F.; Han, F. F.; Zhang, Q.; Xie, T.W.; Lu, L.; Li, S. H.;Xia, H. P. Angew. Chem. Int. Edit. 2013, 52, 5599. doi: 10.1002/anie.201209549

    8. [8]

      (8) Komatsu, H.; Yoshihara, K.; Yamada, H.; Kimura, Y.; Son, A.;Nishimoto, S.; Tanabe, K. Chem. Eur. J. 2013, 19, 1971. doi: 10.1002/chem.v19.6

    9. [9]

      (9) Li, G. Y.; Liu, J. P.; Huang, H. Y.;Wen, Y.; Chao, H.; Ji, L. N.J. Inorg. Biochem. 2013, 121, 108. doi: 10.1016/j.jinorgbio.2012.12.019

    10. [10]

      (10) Clarke, Y.; Xu,W.; Demas, J. N. Anal. Chem. 2000, 72 (15),3468. doi: 10.1021/ac000111g

    11. [11]

      (11) Jain, A.; Xu,W. Y.; Demas, J. N.; Degraff, B. A. Inorg. Chem.1998, 37 (8), 1876. doi: 10.1021/ic971043s

    12. [12]

      (12) Saeksteder, L. A.; Lee, M.; Demas, J. N.; DeGraff, B. A. J. Am. Chem. Soc. 1993, 115 (18), 8230. doi: 10.1021/ja00071a036

    13. [13]

      (13) Seott, L. B.; Demas, J. N. J. Phys. Chem. 1983, 87 (23), 4675.doi: 10.1021/j100246a026

    14. [14]

      (14) Demas, J. N.; Addington, J.W. J. Am. Chem. Soc. 1976, 98 (19),5800. doi: 10.1021/ja00435a010

    15. [15]

      (15) Tang, L. L. Synthesis and Sensing Research of FluorescenceOxygen Sensing Materials Composed of Ruthenium (II)Complex. Ph.D. Dissertation, Southeast University, Nanjing,2012. [唐兰兰. 钌配合物荧光氧敏材料的合成及其传感研究[D]. 南京: 东南大学, 2012]

    16. [16]

      (16) Li, N. Comparative Research of Functional Ligand of NovelFluorescent Oxygen Sensing Complex. Ph.D. Dissertation,Southeast University, Nanjing, 2013. [李楠. 新型荧光氧敏配合物功能化配体的比较研究[D]. 南京: 东南大学, 2013]

    17. [17]

      (17) Wang, F.; Liang,W. J.;Wang,W. G.; Chen, B.; Feng, K.; Zhang,L. P.; Tung, C. H.;Wu, L. Z. Acta Chim. Sin. 2012, 70 (22),2306. [王锋, 梁文静, 王文光, 陈彬, 冯科, 张丽萍, 佟振合, 吴骊珠. 化学学报, 2012, 70 (22), 2306.] doi: 10.6023/A12090687

    18. [18]

      (18) Wu, Y. H.; Zhou, X.;Wang, S.; Bai, F. Q.; Zhang, J. P.; Zhang,H. X.; Sun, J. H. Acta Chim. Sinica. 2009, 67 (1), 33. [吴玉辉, 周欣, 王嵩, 白福全, 张建坡, 张红星, 孙家锺. 化学学报, 2009, 67 (1), 33.]

    19. [19]

      (19) Demas, J. N.; Crosby, G. A. Phys. Chem. 1971, 75 (8), 991. doi: 10.1021/j100678a001

    20. [20]

      (20) Yu, P. F. Chin. J. Lasers 1984, 13, 3. [于佩凤. 中国激光,1984, 13, 3.]

    21. [21]

      (21) Nemkovich, N. A.; Rubinov, A. N.; Savvidi, M. G. Inst. Phys. Conf. Ser. 1991, 126, 639.

    22. [22]

      (22) Krebs, F. C. H. Org. Chem. 2002, 67 (21), 7185. doi: 10.1021/jo025592d

    23. [23]

      (23) Tang, L. G.; Jian, X. G.;Wang, J. Y.; Yin, J. Y. Funct. Mater.2002, 33 (5), 568. [佟拉嘎, 锡高, 王锦艳, 尹军英. 功能材料, 2002, 33 (5), 568.]

    24. [24]

      (24) Kim, H.; Pique, A.; Horwitz, J. S.; Mattoussi, H. Appl. Phys. Lett. 1999, 74 (23), 3444. doi: 10.1063/1.124122

    25. [25]

      (25) Wang, J. X.; Xia, H. Y.; Liu,W. Q.; Zhao, F.;Wang, Y. B. Inorg. Chem. 2013, 393, 92.

    26. [26]

      (26) Becke, A. D. Chem. Phys. 1993, 98, 5648.

    27. [27]

      (27) Lee, C.; Yang,W.; Parr, R. G. Phys. Rev. B 1988, 37, 785. doi: 10.1103/PhysRevB.37.785

    28. [28]

      (28) Wadt,W. R.; Hay, P. J. Chem. Phys. 1985, 82, 284. doi: 10.1063/1.448800

    29. [29]

      (29) Hay, P. J.;Wadt,W. R. Chem. Phys. 1985, 82, 299.

    30. [30]

      (30) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al . Gaussian 03, Revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2003.

    31. [31]

      (31) 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 (7), 1593. [岳炎,许慧霞, 郝玉英, 解晓东, 屈丽桃, 王华, 许并社. 物理化学学报, 2012, 28 (7), 1593.] doi: 10.3866/PKU.WHXB201204181

    32. [32]

      (32) Ren, J. K.; Xu, H. X.; Qu, L. T.; Hao, Y. Y.;Wang, H.; Xu, B. S.Acta Phys. -Chim. Sin. 2013, 29 (5), 1115. [任静琨, 许慧霞,屈丽桃, 郝玉英, 王华, 许并社. 物理化学学报, 2013, 29 (5),1115.] doi: 10.3866/PKU.WHXB201302253


  • 加载中
    1. [1]

      Fa Wang ,  Yu Chen ,  Hui Chao . Ruthenium(II) Complexes as Photoactivated Chemo-Prodrugs for Hypoxic Tumor Therapy. University Chemistry, 2025, 40(7): 200-212. doi: 10.12461/PKU.DXHX202410024

    2. [2]

      Hexing SONG , Zan SUN . Synthesis, crystal structure, Hirshfeld surface analysis, and fluorescent sensing for Fe3+ of an Mn(Ⅱ) complex based on 1-naphthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 885-892. doi: 10.11862/CJIC.20240402

    3. [3]

      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

    4. [4]

      Haihuan YU , Jing SUN , Zhongmin SU . Research progress of water-stable metal-organic frameworks fluorescent sensors in food safety detection. Chinese Journal of Inorganic Chemistry, 2026, 42(8): 1569-1581. doi: 10.11862/CJIC.20260062

    5. [5]

      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

    6. [6]

      Yupeng TANG , Haiying YANG , Fan JIN , Nan LI . Hydrogen storage properties of C6S6Li6: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1827-1839. doi: 10.11862/CJIC.20240460

    7. [7]

      Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N4 site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302

    8. [8]

      Xinrong Wu ,  Yingying Ren ,  Jianxue Wang ,  Lijin Yang ,  Jia Jia ,  Nan Li ,  Na Zhao . 聚光捕胺——高灵敏胺响应型聚集诱导发光探针的合成及传感应用. University Chemistry, 2026, 41(5): 180-189. doi: 10.12461/PKU.DXHX202509129

    9. [9]

      Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079

    10. [10]

      Peipei CUI , Yawen ZHENG , Pan LI , Peiyan GUAN , Zhaohong QIAN . Praseodymium-organic framework with 4, 4′-oxybis(benzoic acid): Rare broken layer structure, antibacterial activity, and sensing for Cd2+ ions. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1641-1649. doi: 10.11862/CJIC.20250152

    11. [11]

      Yu BAI , Jijiang WANG , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A cadmium(Ⅱ) coordination polymer based on a semirigid tetracarboxylate ligand for highly selective detection of Fe3+ and 4-nitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1217-1226. doi: 10.11862/CJIC.20240457

    12. [12]

      Xuetian WANG , Jijiang WANG , Long TANG , Erlin YUE , Xiao WANG , Yuqi ZHANG . A three-dimensional zinc(Ⅱ) metal-organic framework based on nitrogen-containing ligands for the detection of 2,4-dinitrophenylhydrazine and tetracycline. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 861-871. doi: 10.11862/CJIC.20250294

    13. [13]

      Xinyi JIAO , Xin ZHANG , Wanqiao BAI , Xuehua SUN , Huali CUI , Yixia REN , Hongmei CHAI , Loujun GAO . A Eu-based metal-organic framework fluorescent film: Preparation and sensing of Cr2O72- and tryptamine. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 1113-1120. doi: 10.11862/CJIC.20250298

    14. [14]

      Yujing HUANG , Yuan GOU , Kexin JI , Xingcai HUANG , Siyuan CHEN , Jiaojiao KONG , Yanqing WANG . Thiazolo[5,4-d]thiazole fluorophore functionalization in 2D Cd(Ⅱ) metal-organic frameworks triggering a luminescence enhancement for highly sensitive aqueous antibiotic sensing. Chinese Journal of Inorganic Chemistry, 2026, 42(9): 1945-1958. doi: 10.11862/CJIC.20260147

    15. [15]

      Fan LIU , Xiaoli CHEN , Jing REN , Yantao LEI , Huali CUI , Hua YANG , Jijiang WANG . Highly sensitive and multi-response Zn-MOF fluorescence sensor: Design, synthesis, and detection of 4-nitrophenol, Cu2+, and pyrimethanil. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 872-882. doi: 10.11862/CJIC.20250287

    16. [16]

      Zhengkun QIN , Lixin BAO , Yunkai ZHANG , Lin CUI , Jinyu WANG , Yuhao WANG , Mingxing SONG . Theoretical study on the thermally activated delayed fluorescence, and efficiency roll-off characteristics of a series of blue and blue-green Ir(Ⅲ) complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 365-374. doi: 10.11862/CJIC.20250222

    17. [17]

      Meifeng Zhu ,  Jin Cheng ,  Kai Huang ,  Cheng Lian ,  Shouhong Xu ,  Honglai Liu . Classical Density Functional Theory for Understanding Electrochemical Interface. University Chemistry, 2025, 40(3): 148-152. doi: 10.12461/PKU.DXHX202405166

    18. [18]

      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

    19. [19]

      Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395

    20. [20]

      Xingchao Zhao , Xiaoming Li , Ming Liu , Zijin Zhao , Kaixuan Yang , Pengtian Liu , Haolan Zhang , Jintai Li , Xiaoling Ma , Qi Yao , Yanming Sun , Fujun Zhang . Photomultiplication-Type All-Polymer Photodetectors and Their Applications in Photoplethysmography Sensor. Acta Physico-Chimica Sinica, 2025, 41(1): 100007-0. doi: 10.3866/PKU.WHXB202311021

Metrics
  • PDF Downloads(696)
  • Abstract views(1776)
  • HTML views(162)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return