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

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

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