Citation: ZHOU Dan-Hong, LI Miao-Miao, CUI Li-Li. Photophysical Properties and Photoinduced Electron Transfer Mechanism in a Near-IR Fluorescent Probe for Monitoring Peroxynitrite[J]. Acta Physico-Chimica Sinica, ;2013, 29(07): 1453-1460. doi: 10.3866/PKU.WHXB201304244 shu

Photophysical Properties and Photoinduced Electron Transfer Mechanism in a Near-IR Fluorescent Probe for Monitoring Peroxynitrite

1.
Institute of Chemistry for Functionalized Materials, College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, Liaoning Province, P. R. China

Received Date: 18 March 2013
Available Online: 24 April 2013

A heptamethine cyanine dye containing an organoselenium functional group is a near-IR fluorescent probe that operates based on photoinduced electron transfer (PET). This probe can be used for highly sensitive and selective monitoring of peroxynitrite under physiological conditions. In this paper, the photophysical properties and PET mechanism of the probe molecule were investigated by time-dependent density functional theory (TD-DFT) calculations. The results indicated that the excitation in the fluorophore involves an electron transition from the highest occupied molecular orbital (HOMO) to the lowest unoccupied molecular orbital (LUMO). The HOMO level of the recognizer moiety increased in energy above that of the HOMO occupied with a single electron of the fluorophore, leading to transfer of one electron to the heptamethine cyanine moiety, which quenched the fluorescence emission. After the Se moiety was oxidized, the HOMO level of the recognizer moiety decreased in energy, the PET process was prevented, and the fluorescence emission was recovered. It was further proposed that the PET was contributed to by the p electron of the nitrogen atom in the aniline moiety of the probe. The PET efficiency is regulated by the oxidation and reduction events of the organoselenium moiety, resulting in“on-off”fluorescence emission.
- Heptamethine cyanine dye,
- Organoselenium,
- Fluorescence sensor,
- Photoinduced electron transfer,
- Time-dependent density functional theory,
- Excited state
1. [1]
  
  (1) de Silva, A. P.; Gunaratne, H. Q.; Gunnlaugsson, T.; Huxley, A.J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev.1997, 97, 1515. doi: 10.1021/cr960386p
2. [2]
  (2) Zaheer, A.; Lenkinskl, R. E.; Mahmood, A.; Jones, A. G.;Cantley, L. C.; Frangioni, J. V. Nat. Biotechnol. 2001, 19, 1148.doi: 10.1038/nbt1201-1148
3. [3]
  (3) Tang, B.; Yu, F.; Li, P.; Tong, L.; Duan, X.; Xie, T.;Wang, X.J. Am. Chem. Soc. 2009, 131, 3016. doi: 10.1021/ja809149g
4. [4]
  (4) recki, T.; Patonay, G.; Strekowski, L. J. Heterocycl. Chem.1996, 33, 1871. doi: 10.1002/jhet.v33:6
5. [5]
  (5) Yang, C.; Shimelis, O.; Zhou, X.; Li, G.; Bayle, C.; Nertz, M.;Lee, H.; Strekowski, L.; Patonay, G.; Couderc, F.; Giese, R.W.J. Chromatogr. A 2002, 979, 307. doi: 10.1016/S0021-9673(02)01441-3
6. [6]
  (6) Gallaher, D. L.; Johnson, M. E. Analyst 1999, 124, 1541.doi: 10.1039/a904541d
7. [7]
  (7) Yu, F. B.; Li, P.; Li, G. Y.; Zhao, G. J.; Chu, T. S.; Han, K. L.J. Am. Chem. Soc. 2011, 133, 11030. doi: 10.1021/ja202582x
8. [8]
  (8) Rotruck, J. T.; Pope, A. L.; Ganther, H. E.; Swanson, A. B.;Hafeman, D. G.; Hoekstra,W. G. Science 1973, 179, 588.doi: 10.1126/science.179.4073.588
9. [9]
  (9) Nogueira, C.W.; Zeni, G.; Rocha, J. B. Chem. Rev. 2004, 104,6255. doi: 10.1021/cr0406559
10. [10]
  (10) Mugesh, G.; du Mont,W.W.; Sies, H. Chem. Rev. 2001, 101,2125. doi: 10.1021/cr000426w
11. [11]
  (11) Weller, A. Pure Appl. Chem. 1968, 16, 115. doi: 10.1351/pac196816010115
12. [12]
  (12) Rehm, D.;Weller, A. Isr. J. Chem. 1970, 8, 259
13. [13]
  (13) Terai, T.; Kikuchi, K.; Iwasawa, S.; Kawabe, T.; Hirata, Y.;Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2006, 128, 6938.
14. [14]
  (14) Petsalakis, I. D.; Lathiotakis, N. N.; Theodorakopoulos, G.J. Mol. Struct.-Theochem 2008, 867, 64. doi: 10.1016/j.theochem.2008.07.025
15. [15]
  (15) Salman, H.; Tal, S.; Chuvilov, Y.; Solovey, O.; Abraham, Y.;Kapon, M.; Suwinska, K.; Eichen, Y. Inorg. Chem. 2006, 45 (14), 5315. doi: 10.1021/ic051897+
16. [16]
  (16) Han, F.; Chi, L.; Liang, X.; Ji, S.; Liu, S.; Zhou, F.;Wu, Y.; Han,K.; Zhao, J.; James, T. D. J. Org. Chem. 2009, 74 (3), 1333.doi: 10.1021/jo8025669
17. [17]
  (17) Chi, L. N.;Wu, Y. B.; Zhang, X.; Ji, S. M.; Shao, J. Y.; Guo, H.M.;Wang, X.; Zhao, J. Z. J. Fluores. 2010, 20, 1255.doi: 10.1007/s10895-010-0677-2
18. [18]
  (18) Becke, A. D. J. Chem. Phys. 1993, 98, 5648. doi: 10.1063/1.464913
19. [19]
  (19) dbout, N.; Salahub, D. R.; Andzelm, J.;Wimmer, E. Can. J. Chem. 1992, 70, 560. doi: 10.1139/v92-079
20. [20]
  (20) Foster, J. P.;Weinhold, F. J. Am. Chem. Soc. 1980, 102 (24),7211.
21. [21]
  (21) Gross, E. K. U.; Kohn,W. Phys. Rev. Lett. 1985, 55 (26), 2850.doi: 10.1103/PhysRevLett.55.2850
22. [22]
  (22) Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys.1998, 109, 8218. doi: 10.1063/1.477483
23. [23]
  (23) Vosko, S. H.;Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.doi: 10.1139/p80-159
24. [24]
  (24) Xu,W. H.; Zhang, Y.; Liu,W. J. Science in China B-Chemistry2009, 39 (11), 1484. [许文华, 张勇, 刘文剑. 中国科学B辑: 化学, 2009, 39 (11), 1484.]
25. [25]
  (25) Becke, A. D. Phys. Rev. A 1988, 38 (6), 3098. doi: 10.1103/PhysRevA.38.3098
26. [26]
  (26) Perdew, J. P. Phys. Rev. B 1986, 33, 8832.
27. [27]
  (27) Treutler, O.; Ahlrichs, R. J. Chem. Phys. 1995, 102, 346.doi: 10.1063/1.469408
28. [28]
  (28) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Chem. Phys.2001, 114, 5691. doi: 10.1063/1.1354187
29. [29]
  (29) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem.2003, 24, 669. doi: 10.1002/jcc.10189
30. [30]
  (30) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 03,Revision E.01; Gaussian Inc.:Wallingford, CT, 2010.
31. [31]
  (31) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 09,Revision B.01; Gaussian Inc.:Wallingford, CT, 2004.
32. [32]
  (32) Eckert, F.; Klamt, A. AIChE J. 2002, 48, 369.
33. [33]
  (33) Awuah, S. G.; Polreis, J.; Biradar, V.; You, Y. Org. Lett. 2011, 13 (15), 3884. doi: 10.1021/ol2014076
34. [34]
  (34) Wang, Y. L.;Wu, G. S. Acta Phys. -Chim. Sin. 2007, 23, 1831.[王溢磊, 吴国是. 物理化学学报, 2007, 23, 1831.] doi: 10.1016/S1872-1508(07)60086-2
35. [35]
  (35) Liu, X. J.;Wang, N,; Cheng, H. Acta Phys. -Chim. Sin. 2011, 27,1640. [刘小君, 王宁, 程浩. 物理化学学报, 2011, 27,1640.] doi: 10.3866/PKU.WHXB20110718
36. [36]
  (36) Liu, X. J.; Lin, T.; Gao, S.W.; Ma, R.; Zhang, J. Y.; Cai, X. C.;Yang, L.; Teng, F. Acta Phys. -Chim. Sin. 2012, 28, 1337.[刘小君, 林涛, 高少伟, 马睿, 张晋悦, 蔡新晨, 杨磊,滕枫. 物理化学学报, 2012, 28, 1337.] doi: 10.3866/PKU.WHXB201204092
37. [37]
  (37) Wang, F. J.; Zhou, D. H.; Zuo, S. Y.; Cao, J. F.; Peng, X. J. Acta Phys. -Chim. Sin. 2012, 28, 1645. [王凤娇, 周丹红, 左士颖,曹建芳, 彭孝军. 物理化学学报, 2012, 28, 1645.] doi: 10.3866/PKU.WHXB201205083
38. [38]
  (38) Ren, X. F.; Ren, A. M.;Wang, Q.; Feng, J. K. Acta Phys. -Chim. Sin. 2010, 26, 110. [任雪峰, 任爱民, 王钦, 封继康.物理化学学报, 2010, 26, 110.] doi: 10.3866/PKU.WHXB20100103
39. [39]
  (39) Zhao, P.; Xu, L. C.; Ma, L. Acta Phys. -Chim. Sin. 2011, 27,2541. [赵平, 绪连彩, 马丽. 物理化学学报, 2011, 27,2541.] doi: 10.3866/PKU.WHXB20111021
1. [1]
  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
2. [2]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
3. [3]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
4. [4]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
5. [5]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . Kinetic Resolution Enabled by Photoexcited Chiral Copper Complex-Mediated Alkene E→Z Isomerization: A Comprehensive Chemistry Experiment for Undergraduate Students. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
6. [6]
  Bao Jia , Yunzhe Ke , Shiyue Sun , Dongxue Yu , Ying Liu , Shuaishuai Ding . Innovative Experimental Teaching for the Preparation and Modification of Conductive Organic Polymer Thin Films in Undergraduate Courses. University Chemistry, 2024, 39(10): 271-282. doi: 10.12461/PKU.DXHX202404121
7. [7]
  Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
8. [8]
  Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431
9. [9]
  Yue Wu , Jun Li , Bo Zhang , Yan Yang , Haibo Li , Xian-Xi Zhang . Research on Kinetic and Thermodynamic Transformations of Organic-Inorganic Hybrid Materials for Fluorescent Anti-Counterfeiting Application information: Introducing a Comprehensive Chemistry Experiment. University Chemistry, 2024, 39(6): 390-399. doi: 10.3866/PKU.DXHX202403028
10. [10]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
11. [11]
  Tao Cao , Fang Fang , Nianguang Li , Yinan Zhang , Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
12. [12]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
13. [13]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
14. [14]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
15. [15]
  Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
16. [16]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
17. [17]
  Shicheng Yan . Experimental Teaching Design for the Integration of Scientific Research and Teaching: A Case Study on Organic Electrooxidation. University Chemistry, 2024, 39(11): 350-358. doi: 10.12461/PKU.DXHX202408036
18. [18]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
19. [19]
  Tengjiao Wang , Tian Cheng , Rongjun Liu , Zeyi Wang , Yuxuan Qiao , An Wang , Peng Li . Conductive Hydrogel-based Flexible Electronic System: Innovative Experimental Design in Flexible Electronics. University Chemistry, 2024, 39(4): 286-295. doi: 10.3866/PKU.DXHX202309094
20. [20]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351

Get Citation

PDF

XML

Metrics

PDF Downloads(902)
Abstract views(1248)
HTML views(39)

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