红移型Cu(II)离子比率荧光探针的光物理性质

doi:10.3866/PKU.WHXB201302064

Abstract

Abstract:

Density functional theory (DFT) and time-dependent DFT (TDDFT) were used to study the photophysical properties of N-butyl-4,5-di[2-(phenylamino)ethylamino]-1,8-naphthalimide, a ratiometric fluorescent sensor for Cu(II). The geometric structures of the compounds at the ground state were optimized by DFT. Combined with natural bond orbital (NBO) analysis, the binding characteristics of the chemosensor molecule coordinated with a Cu(II) ion were identified. The excitation states of the compounds were investigated and the internal charge transfer (ICT) mechanism was elucidated by theoretical calculations. The results indicated that the coordinated Cu(II) ion induced the dehydrogenation of naphthylamine. The negatively-charged amino N atom then formed a C＝N double bond with the naphthalene ring, extending the conjugation of the system. The nonbonding electron of N was transferred to the unoccupied d orbital of Cu(II), preventing fluorescence quenching by paramagnetic Cu(II). It was proposed that in the excited state, n→π^* electron transfer from the amino N to the naphthalene ring led to internal charge transfer and resulted in the red shift of fluorescence.

Key words: 4,5-Di(alkylamino)-1,8-naphthalimide, Copper ion fluorescent chemosensor, Internal charge transfer, Red-shift in fluorescence spectrum, Time-dependent density function theory

MSC2000:

O641

CUI Li-Li, ZHOU Dan-Hong, LI Miao-Miao. Photophysical Properties of a Red-Shift Cu(II) Ratiometric Fluorescent Chemosensor[J].Acta Phys. -Chim. Sin., 2013, 29(04): 745-753.

References

(1) Tapiero,H.; Townsend,D.M.; Tew,K.D. Biomed. Pharmacother2003, 57, 386. doi: 10.1016/S0753-3322(03)00012-X
(2) Linder, M. C.; Hazegh-Azam, M. Am. J. Clin. Nutr. 1996, 63,797S.
(3) Uauy, R.; Olivares, M.; Gonzalez, M. Am. J. Clin. Nutr. 1998,67 (suppl), 952S.
(4) Rurack, K. Spectrochim. Acta A 2001, 57 (11), 2161. doi: 10.1016/S1386-1425(01)00492-9
(5) Zheng, Y. J.; Orbulescu, J.; Ji, X. J.; Andreopoulos, F. M.;Pham, S. M.; Leblanc, R. M. J. Am. Chem. Soc. 2003, 125,2680. doi: 10.1021/ja0293610
(6) Hou, F. P.; Huang, L.; Xi, P. X.; Cheng, J.; Zhao, X. F.; Xie, G.Q.; Shi, Y. J.; Cheng, F. J.; Yao, X. J.; Bai, D. C.; Zeng, Z. Z.Inorg. Chem. 2012, 51, 2454. doi: 10.1021/ic2024082
(7) Zhou, Y. M.; Zhang, J. L.; Zhou, H.; Zhang, Q. Y.; Ma, T. S.;Niu, J. Y. Journal of Luminescence 2012, 132, 1837. doi: 10.1016/j.jlumin.2012.03.016
(8) Kaur, S.; Kumar, S. Chem. Commun. 2002, 2840.
(9) Banthia, S.; Samanta, A. J. Phys. Chem. B 2002, 106 (21), 5572.doi: 10.1021/jp014546z
(10) Mashraqui, S. H.; Chandiramani, M.; Betkar, R.; Ghorpade, S.Sensors and Actuators B 2010, 150, 574. doi: 10.1016/j.snb.2010.08.037
(11) Xu, Z. C.; Pan, J.; Spring, D. R.; Cui, J. N.; Yoon, J. Y.Tetrahedron 2010, 66, 1678. doi: 10.1016/j.tet.2010.01.008
(12) Zhu, H.; Fan, J. L.; Lu, J.; Hu, M. M.; Cao, J. F.;Wang, J.; Li,H. L.; Liu, X. J.; Peng, X. J. Talanta 2012, 93, 55. doi: 10.1016/j.talanta.2012.01.024
(13) Fan, J. L.; Liu, X. J.; Hu, M. M.; Zhu, H.; Song, F. L.; Peng, X.J. Analytica Chimica Acta 2012, 735, 107. doi: 10.1016/j.aca.2012.05.027
(14) Zhao, T. F.; Zhao, D. F.; Yu, H. Y.; Cheng, L. B. DyestuffIndustry 1997, 34 (1), 8. [赵同丰, 赵德丰, 于华云, 程侣柏.染料工业, 1997, 34 (1), 8.]
(15) Xu, Z. C.; Xiao, Y.; Qian, X. H.; Cui, J. N.; Cui, D.W. Org.Lett. 2005, 7 (5), 889. doi: 10.1021/ol0473445
(16) Xu, Z. C.; Qian, X. H.; Cui, J. N. Org. Lett. 2005, 7 (14), 3029.doi: 10.1021/ol051131d
(17) Furche, F.; Rappoport, D. J. Am. Chem. Soc. 2004, 126 (4),1277. doi: 10.1021/ja037806u
(18) Duan, X. H.; Li, X. Y.; He, R. X.; Cheng, X. M. J. Chem. Phys.2005, 122 (8), 084314. doi: 10.1063/1.1850097
(19) Demeter, A.; Bérces, T.; Biczók, L.;Wintgens, V.; Valat, P.;Kossanyi, J. J. Phys. Chem. 1996, 100 (6), 2001. doi: 10.1021/jp951133n
(20) Duan, X. H.; Pei, Z. H.; Ma, Y. J. Science in China Series B:Chemistry 2008, 38 (3), 232. [段晓惠, 裴重华, 马拥军.中国科学B辑: 化学, 2008, 38 (3), 232.]
(21) Paul, B. K.; Samanta, A.; Kar, S.; Guchhait, N. Journal ofLuminescence 2010, 130 (7), 1258. doi: 10.1016/j.jlumin.2010.02.036
(22) Becke, A. D. J. Chem. Phys. 1993, 98, 5648. doi: 10.1063/1.464913
(23) Foster, J. P.;Weinhold, F. J. Am. Chem. Soc. 1980, 102 (24),7211. doi: 10.1021/ja00544a007
(24) Gross, E. K. U.; Kohn,W. Physical Review Letters 1985, 55 (26), 2850. doi: 10.1103/PhysRevLett.55.2850
(25) Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys.1998, 109, 8218. doi: 10.1063/1.477483
(26) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Chem. Phys.2001, 114, 5691.
(27) Wang, Y. L.;Wu, G. S. Acta Phys. -Chim. Sin. 2008, 24, 552.[王溢磊, 吴国是. 物理化学学报, 2008, 24, 552.] doi: 10.1016/S1872-1508(08)60021-2
(28) Zhang, J. B.; Jin, L.; Zhang, H. X. Acta Phys. -Chim. Sin. 2011,27, 1089. [张建坡, 金丽, 张红星. 物理化学学报, 2011, 27,1089.] doi: 10.3866/PKU.WHXB20110505
(29) 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
(30) Becke, A. D. Phys. Rev. A 1988, 38 (6), 3098. doi: 10.1103/PhysRevA.38.3098
(31) Vosko, S. H.;Wilk, L.; Nusair, M. Canadian Journal of Physics1980, 58, 1200.
(32) Xu,W. H.; Zhang, Y.; Liu,W. J. Science in China Series B:Chemistry 2009, 39 (11), 1484. [许文华, 张勇, 刘文剑.中国科学B辑: 化学, 2009, 39 (11), 1484.]
(33) Perdew, J. P. Phys. Rev. B 1986, 33, 8832.
(34) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 03,Revision E.01; Gaussian Inc.:Wallingford, CT, 2004.
(35) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B. et al. Gaussian 09,Revision B.01; Gaussian Inc.:Wallingford, CT, 2010.
(36) Wang, F. J.; Zhou, D. H.; Zuo, S. Y.; Cao, J. F.; Peng, X. J. ActaPhys. -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

[1]	LI Haixia, WANG Jiwei, JIAO Lifang, TAO Zhanliang, LIANG Jing. Spherical Nano-SnSb/C Composite as a High-Performance Anode Material for Sodium Ion Batteries [J]. Acta Physico-Chimica Sinica, 0, (): 1904017-0.
[2]	Xuezhu Xiao, Xiaofang Cao, Dongbo Zhao, Chunying Rong, Shubin Liu. Quantification of Molecular Basicity for Amines: a Combined Conceptual Density Functional Theory and Information-Theoretic Approach Study [J]. Acta Physico-Chimica Sinica, 0, (): 1906034-0.
[3]	Jinxiu Zhan, Feng Feng, Ming Xu, Li Yao, Maofa Ge. Progress in Chemo-Mechanical Interactions between Nanoparticles and Cells [J]. Acta Physico-Chimica Sinica, 0, (): 1905076-0.
[4]	Zhen Wei, Minjie Li, Wencong Lu. Theoretical Study of High-Efficiency Organic Dyes with Different Electron-Withdrawing Groups Based on R6 Toward Dye-Sensitized Solar Cells [J]. Acta Physico-Chimica Sinica, 0, (): 1905084-0.
[5]	Junjie Shi, Ziqi Hu, Yihao Yang, Yuxiang Bu, Zujin Shi. Stability and Formation Mechanism of Endohedral Metal Carbonitride Clusterfullerenes [J]. Acta Physico-Chimica Sinica, 0, (): 1907077-0.
[6]	Aoneng Cao. “Confined Lowest Energy Structure Fragments (CLESFs)” Hypothesis for Protein Structure and the “Stone Age” of Protein Prebiotic Evolution [J]. Acta Physico-Chimica Sinica, 0, (): 1907002-0.
[7]	Minyi Su, Huisi Liu, Haixia Lin, Renxiao Wang. Machine-Learning Model for Predicting the Rate Constant of Protein-Ligand Dissociation [J]. Acta Physico-Chimica Sinica, 0, (): 1907006-0.
[8]	Sirui Liu, Hui Quan, Hao Tian, Rui Zhou, Lijiang Yang, Yiqin Gao. 1D Sequence Based 3D Chromatin Phase Separation: Forces, Processes, and Functions [J]. Acta Physico-Chimica Sinica, 0, (): 1907010-0.
[9]	DENG Jing, MA Tao, CHANG Ziwei, ZHAO Weijing, YANG Jun. Determination of Three-Dimensional Structures of Protein Assemblies via Solid-State NMR [J]. Acta Physico-Chimica Sinica, 0, (): 1905019-0.
[10]	Jian Li, Cong Lin, Jianhua Lin, Junliang Sun. Application of Combining X-ray Diffraction and Electron Crystallography for Determination of Complex Inorganic Crystal Structure [J]. Acta Physico-Chimica Sinica, 0, (): 1907052-0.
[11]	Ziyi Liu, Miaoren Xia, Zhifang Chai, Dongqi Wang. Parameterization and Validation of AMBER Force Field for Np⁴⁺, Am³⁺, and Cm³⁺ [J]. Acta Physico-Chimica Sinica, 0, (): 1908035-0.
[12]	Changsheng Zhang, Luhua Lai. Physiochemical Mechanisms of Biomolecular Liquid-Liquid Phase Separation [J]. Acta Physico-Chimica Sinica, 0, (): 1907053-0.
[13]	Sa Chen, Ran Shang, Bingwu Wang, Zheming Wang, Song Gao. An Anisotropic Diluted Magnetic Hybrid Perovskite Series of[CH₃NH₃] [Co_xZn_1-x(HCOO)₃] [J]. Acta Physico-Chimica Sinica, 0, (): 1907012-0.
[14]	QIAO Chengfang, LÜ Lei, XU Wenfeng, XIA Zhengqiang, ZHOU Chunsheng, CHEN Sanping, GAO Shengli. Synthesis, Thermal Decomposition Kinetics and Detonation Performance of a Three-Dimensional Solvent-Free Energetic Ag(I)-MOF [J]. Acta Physico-Chimica Sinica, 0, (): 1905085-0.
[15]	Hantao Sun, Jianhui Liao, Shimin Hou. Single-Molecule Field-Effect Transistors with Graphene Electrodes and Covalent Pyrazine Linkers [J]. Acta Physico-Chimica Sinica, 0, (): 1906027-0.

Photophysical Properties of a Red-Shift Cu(II) Ratiometric Fluorescent Chemosensor

PDF (PC)

Like

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Metrics

Comments

Recommended 10