Citation: ZHAO Ping, XU Lian-Cai, MA Li. Spectral Research into Intramolecular Photoinduced Electron Transfer of Porphyrin-Anthraquinone Hybrids[J]. Acta Physico-Chimica Sinica, ;2011, 27(11): 2541-2546. doi: 10.3866/PKU.WHXB20111021 shu

Spectral Research into Intramolecular Photoinduced Electron Transfer of Porphyrin-Anthraquinone Hybrids

ZHAO Ping ^1, ,
XU Lian-Cai ² ,
MA Li ³

1.
1. School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Zhongshan 528458, Guangdong Province, P. R. China;
2. School of Material and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, P. R. China;
3. College of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou 450001, P. R. China

Received Date: 29 July 2011
Available Online: 19 August 2011
Fund Project: 广东省医学科研项目(B2010158)资助 (B2010158)

A series of covalently linked porphyrin (Por)-anthraquinone (AQ) hybrids Por-C_n-AQ (n=1, 4, 10) with flexible different length carbon chains were synthesized and their intramolecular photoinduced electron transfer (PET) properties were investigated mainly by steady-state fluorescence and decayed luminescence spectra. We studied the PET mechanism using density functional theory (DFT). We found that PET occurs from the porphyrin moiety to the anthraquinone moiety of these dyads and that the PET efficiency is influenced considerably by the length of the linkage between the two moieties in the hybrids. From both the experimental and theoretical results, we can conclude that the PET of these dyads is seemingly most compatible with a“through-bond”(super-exchange) mechanism.
- Porphyrin-anthraquinone dyad,
- Electron transfer,
- Fluorescence spectrum,
- Density functional theory
1. [1]
  (1) Adriana, A. R. M.;Walderez, G.; Mauro, C. G.; Márcia, A. S. Int. Biodeter. Biodegr. 2011, 65, 423.
2. [2]
  (2) Nathan, C.; Kerry, B. B.; Zhou, X. J.; Samuel, J. L.; Keith, C. G.; Timothy,W. J.; Paul, C. D.;Warwick, J. B. Sol. Energy Mater. Sol. Cells 2011, 95, 1767.
3. [3]
  (3) Bhattacharya, S.; Nayak, S. K.; Chattopadhyay, S.; Saha, D. J. Mol. Liq. 2008, 143, 125.
4. [4]
  (4) Hirakawa, K.; Segawa, H. J. Photochem. Photobiol. A 2010, 213, 73.
5. [5]
  (5) Tao, M. L.; Liu, L. Z.; Liu, D. Z.; Zhou, X. Q. Dyes Pigm. 2010, 85, 21.
6. [6]
  (6) Odobel, F.; Fortage, J. C. R. Chim. 2009, 12, 437.
7. [7]
  (7) Shibano, Y.; Sasaki, M.; Tsuji, H.; Araki, Y.; Ito, O.; Tamao, K. J. Organomet. Chem. 2007, 692, 356.
8. [8]
  (8) Durmus, M.; Chen, J. Y.; Zhao, Z. X.; Nyokong, T. Spectrochim. Acta A 2008, 70, 42.
9. [9]
  (9) Poon, C. T.; Zhao, S. S.;Wong,W. K.; Kwong, D.W. J. Tetrahedron Lett. 2010, 51, 664.
10. [10]
  (10) Zhao, J.W.; Liu, H. M.; Ni,W. B.; Guo, Y.; Yin, X. Acta Phys. -Chim. Sin. 2009, 25, 1472.
11. [11]
  [赵健伟, 刘洪梅, 倪文彬, 郭彦, 尹星. 物理化学学报, 2009, 25, 1472.]
12. [12]
  (11) Ren, X. F.; Ren, A. M.;Wang, Q.; Feng, J. K. Acta Phys. -Chim. Sin. 2010, 26, 110.
13. [13]
  [任雪峰, 任爱民, 王钦, 封继康. 物理化学学报, 2010, 26, 110.]
14. [14]
  (12) Liu, J.; Huang, J.W.; Shen, H.;Wang, H.; Yu, H. C.; Ji, L. N. Dyes Pigm. 2008, 77, 374.
15. [15]
  (13) Miao, D.; Xu, Y. Z.; Yang, J.; Xu, Z. H. Spectrochim. Acta A 2004, 24, 513.
16. [16]
  [苗笛, 徐怡庄, 杨军, 许振华. 光谱学与光谱分析, 2004, 24, 513.]
17. [17]
  (14) Perun, S.; Tatchen, J.; Marian, C. M. Chem. Phys. Chem. 2008, 9, 282.
18. [18]
  (15) Li, C.; Zhang, L.; Zhang, C.; Hirao, H.;Wu,W.; Shaik, S. Angew. Chem. Int. Edit. 2007, 46, 8168.
19. [19]
  (16) Zhang, X.; Muranaka, A.; Lu,W.; Zhang, Y.; Bian, Y.; Jiang, J.; Kobayashi, N. Chem. Eur. J. 2008, 14, 4667.
20. [20]
  (17) Zhang, Y. H.; Ruan,W. J.;Wu, Y. Acta Phys. -Chim. Sin. 2005, 21, 1390.
21. [21]
  [章应辉, 阮文娟, 吴扬. 物理化学学报, 2005, 21, 1390.]
22. [22]
  (18) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
23. [23]
  (19) Rassolov, V. A.; Pople, J. A.; Ratner, M. A.;Windus, T. L. J. Chem. Phys. 1998, 109, 1223.
24. [24]
  (20) Zhurko, G. A.; Zhurko, D. A. Chemcraft, Version 1.6; Plimus, Inc.: Milpitas, USA, 2011.
25. [25]
  (21) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al . Gaussian 03, Revision D.01; Gaussian Inc.:Wallingford, CT, 2004.
26. [26]
  (22) Huang, J.W.; Ji, L. N. Chem. J. Chin. Univ. 1995, 16, 163.
27. [27]
  [黄锦汪, 计亮年. 高等学校化学学报, 1995, 16, 163.]
28. [28]
  (23) Maza,W. A.; Larsen, R.W. Biophys. J. 2010, 98, 565.
29. [29]
  (24) Hutchison, J. A.; Bell, T. D. M.; Ganguly, T.; Ghiggino, K. P.; Langford, S. J.; Lokan, N. R.; Paddon-Row, M. N. J. Photochem. Photobiol. A 2008, 197, 220.
30. [30]
  (25) Karr, P. A.; Zandler, M. E.; Beck, M.; Jaeger, J. D.; McCarty, A. L.; Smith, P. M.; D'Souza, F. J. Mol. Struct. 2006, 765, 91.
31. [31]
  (26) Le, X. Y.; Ji, L. N.;Wu, F. H.; Song, F. Y. Chin. Sci. Bull. 1997, 42, 1103.
32. [32]
  [乐学义, 计亮年, 毋福海, 宋粉云. 科学通报. 1997, 42, 1103.]
33. [33]
  (27) Le, X. Y.; Ji, L. N. Chin. Sci. Bull. 2001, 46, 1235.
34. [34]
  [乐学义, 计亮年. 科学通报, 2001, 46, 1235.]
35. [35]
  (28) Ren, Q. Z.; Huang, J.W.; Lin, C. Y.; Ji, L. N. Chem. J. Chin. Univ. 1999, 20, 333.
36. [36]
  [任奇志, 黄锦汪, 林翠梧, 计亮年. 高等学校化学学报, 1999, 20, 333.]
37. [37]
  (29) Kuznetaov, A. M.; Ulstrup, J. J. Chem. Phys. 1981, 75, 2074.
38. [38]
  (30) Warman, J. M. Nature 1986, 320, 615.
1. [1]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
2. [2]
  Chun-Lin Sun , Yaole Jiang , Yu Chen , Rongjing Guo , Yongwen Shen , Xinping Hui , Baoxin Zhang , Xiaobo Pan . Construction, Performance Testing, and Practical Applications of a Home-Made Open Fluorescence Spectrometer. University Chemistry, 2024, 39(5): 287-295. doi: 10.3866/PKU.DXHX202311096
3. [3]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
4. [4]
  Xiaochen Zhang , Fei Yu , Jie Ma . 多角度数理模拟在电容去离子中的前沿应用. Acta Physico-Chimica Sinica, 2024, 40(11): 2311026-. doi: 10.3866/PKU.WHXB202311026
5. [5]
  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
6. [6]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
7. [7]
  Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . 六氯锡酸铵促进钙钛矿太阳能电池界面电子转移及其飞秒瞬态吸收光谱研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-. doi: 10.3866/PKU.WHXB202402006
8. [8]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
9. [9]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
10. [10]
  Jiaxin Su , Jiaqi Zhang , Shuming Chai , Yankun Wang , Sibo Wang , Yuanxing Fang . Optimizing Poly(heptazine imide) Photoanodes Using Binary Molten Salt Synthesis for Water Oxidation Reaction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408012-. doi: 10.3866/PKU.WHXB202408012
11. [11]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
12. [12]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
13. [13]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
14. [14]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
15. [15]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
16. [16]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
17. [17]
  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
18. [18]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
19. [19]
  Jinfeng Chu , Lan Jin , Yu-Fei Song . Exploration and Practice of Flipped Classroom in Inorganic Chemistry Experiment: a Case Study on the Preparation of Inorganic Crystalline Compounds. University Chemistry, 2024, 39(2): 248-254. doi: 10.3866/PKU.DXHX202308016
20. [20]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033

Get Citation

PDF

XML

Metrics

PDF Downloads(1287)
Abstract views(3196)
HTML views(58)

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