Responsive mechanism and molecular design of di-2-picolylamine-based two-photon fluorescent probes for zinc ions

doi:10.1088/1674-1056/27/2/023302

中国物理B ›› 2018, Vol. 27 ›› Issue (2): 23302-023302.doi: 10.1088/1674-1056/27/2/023302

• ATOMIC AND MOLECULAR PHYSICS • 上一篇下一篇

Responsive mechanism and molecular design of di-2-picolylamine-based two-photon fluorescent probes for zinc ions

Mei-Yu Zhu(朱美玉), Ke Zhao(赵珂), Jun Song(宋军), Chuan-Kui Wang(王传奎)

School of Physics and Electronics, Shandong Normal University, Jinan 250358, China

收稿日期:2017-09-07 修回日期:2017-10-23 出版日期:2018-02-05 发布日期:2018-02-05
通讯作者: Ke Zhao E-mail:zhaoke@sdnu.edu.cn
基金资助:
Project supported by the Shandong Provincial Natural Science Foundation, China (Grant No. ZR2014AM026), the National Natural Science Foundation of China (Grant Nos. 11374195 and 11404193), and the Taishan Scholar Project of Shandong Province, China.

Responsive mechanism and molecular design of di-2-picolylamine-based two-photon fluorescent probes for zinc ions

Mei-Yu Zhu(朱美玉), Ke Zhao(赵珂), Jun Song(宋军), Chuan-Kui Wang(王传奎)

School of Physics and Electronics, Shandong Normal University, Jinan 250358, China

Received:2017-09-07 Revised:2017-10-23 Online:2018-02-05 Published:2018-02-05
Contact: Ke Zhao E-mail:zhaoke@sdnu.edu.cn
About author:33.20.-t; 42.65.-k; 82.30.Fi
Supported by:
Project supported by the Shandong Provincial Natural Science Foundation, China (Grant No. ZR2014AM026), the National Natural Science Foundation of China (Grant Nos. 11374195 and 11404193), and the Taishan Scholar Project of Shandong Province, China.

摘要/Abstract

摘要： The properties of one-photon absorption (OPA), emission and two-photon absorption (TPA) of a di-2-picolylamine-based zinc ion sensor are investigated by employing the density functional theory in combination with response functions. The responsive mechanism is explored. It is found that the calculated OPA and TPA properties are quite consistent with experimental data. Because the intra-molecular charge transfer (ICT) increases upon zinc ion binding, the TPA intensity is enhanced dramatically. According to the model sensor, we design a series of zinc ion probes which differ by conjugation center, acceptor and donor moieties. The properties of OPA, emission and TPA of the designed molecules are calculated at the same computational level. Our results demonstrate that the OPA and emission wavelengths of the designed probes have large red-shifts after zinc ions have been bound. Comparing with the model sensor, the TPA intensities of the designed probes are enhanced significantly and the absorption positions are red-shifted to longer wavelength range. Furthermore, the TPA intensity can be improved greatly upon zinc ion binding due to the increased ICT mechanism. These compounds are potential excellent candidates for two-photon fluorescent zinc ion probes.

关键词: two-photon absorption, fluorescent probe, zinc ion, intra-molecular charge transfer

Abstract: The properties of one-photon absorption (OPA), emission and two-photon absorption (TPA) of a di-2-picolylamine-based zinc ion sensor are investigated by employing the density functional theory in combination with response functions. The responsive mechanism is explored. It is found that the calculated OPA and TPA properties are quite consistent with experimental data. Because the intra-molecular charge transfer (ICT) increases upon zinc ion binding, the TPA intensity is enhanced dramatically. According to the model sensor, we design a series of zinc ion probes which differ by conjugation center, acceptor and donor moieties. The properties of OPA, emission and TPA of the designed molecules are calculated at the same computational level. Our results demonstrate that the OPA and emission wavelengths of the designed probes have large red-shifts after zinc ions have been bound. Comparing with the model sensor, the TPA intensities of the designed probes are enhanced significantly and the absorption positions are red-shifted to longer wavelength range. Furthermore, the TPA intensity can be improved greatly upon zinc ion binding due to the increased ICT mechanism. These compounds are potential excellent candidates for two-photon fluorescent zinc ion probes.

Key words: two-photon absorption, fluorescent probe, zinc ion, intra-molecular charge transfer

中图分类号: (Molecular spectra)

33.20.-t

42.65.-k (Nonlinear optics) 82.30.Fi (Ion-molecule, ion-ion, and charge-transfer reactions)

朱美玉, 赵珂, 宋军, 王传奎. Responsive mechanism and molecular design of di-2-picolylamine-based two-photon fluorescent probes for zinc ions[J]. 中国物理B, 2018, 27(2): 23302-023302.

Mei-Yu Zhu(朱美玉), Ke Zhao(赵珂), Jun Song(宋军), Chuan-Kui Wang(王传奎). Responsive mechanism and molecular design of di-2-picolylamine-based two-photon fluorescent probes for zinc ions[J]. Chin. Phys. B, 2018, 27(2): 23302-023302.

参考文献 36

[1]	Denk W, Strickler J H and Webb W W 1990 Science 248 73
[2]	Yao S and Belfield K D 2012 Eur. J. Org. Chem. 2012 3199
[3]	Kim D, Ryu H G and Ahn K H 2014 Org. Biomol. Chem. 12 4550
[4]	Kim H M and Cho B R 2015 Chem. Rev. 115 5014
[5]	Kim H M and Cho B R 2011 Chem. Asian J. 6 58
[6]	Sarkar A R, Kang D E, Kim H M and Cho B R 2014 Inorg. Chem. 53 1794
[7]	Sumalekshmy S and Fahrni C J 2011 Chem. Mater. 23 483
[8]	Kim D, Singha S, Wang T, Seo E, Lee J H, Lee S J, Kim K H and Ahn K H 2012 Chem. Commun. 48 10243
[9]	Kim H M, An M J, Hong J H, Jeong B H, Kwon O, Hyon J Y, Hong S C, Lee K J and Cho B R 2008 Angew. Chem. Int. Ed. 47 2231
[10]	Kim H J, Heo C H and Kim H M 2013 J. Am. Chem. Soc. 135 17969
[11]	Das S K, Lim C S, Yang S Y, Han J H and Cho B R 2012 Chem. Commun. 48 8395
[12]	Masanta G, Heo C H, Lim C S, Bae S K, Cho B R and Kim H M 2012 Chem. Commun. 48 3518
[13]	Zhang Y, Wang J, Jia P, Yu X, Liu H, Liu X, Zhao N and Huang B 2010 Org. Biomol. Chem. 8 4582
[14]	Pawlicki M, Collins H A, Denning R G and Anderson H L 2009 Angew. Chem. Int. Ed. 48 3244
[15]	Kim H M and Cho B R 2009 Chem. Commun. 0 153
[16]	Bush A I, Pettingell W H, Multhaup G, Paradis M d, Vonsattel J P, Gusella J F, Beyreuther K, Masters C L and Tanzi R E 1994 Science 265 1464
[17]	Cuajungco M P and Lees G J 1997 Neurobiol. Dis. 4 137
[18]	Bush A I and Tanzi R E 2002 Proc. Natl. Acad. Sci. USA 99 7317
[19]	Wang D, Guo J F, Ren A M, Huang S, Zhang L and Feng J K 2014 J. Phys. Chem. B 118 10101
[20]	Bednarska J, Zaleśny R, Murugan N A, Bartkowiak W, Ågren H and Odelius M 2016 J. Phys. Chem. B 120 9067
[21]	Zhang Y J, Zhang Q Y, Ding H J, Song X N and Wang C K 2015 Chin. Phys. B 24 023301
[22]	Huang S, Yang B Z, Jiang X F and Ren A M 2016 J. Mol. Model. 22 34
[23]	Mukherjee T, Pessoa J C, Kumar A and Sarkar A R 2012 Dalton Trans. 41 5260
[24]	Zhao K, Liu P W, Wang C K and Luo Y 2010 J. Phys. Chem. B 114 10814
[25]	Wang F Q, Zhao K, Zhu M Y and Wang C K 2016 J. Phys. Chem. B 120 9708
[26]	Wu X L, Zhao K, Jia H H and Wang F Q 2015 Acta Phys. Sin. 64 233301(in Chinese)
[27]	Zhao K, Han G C, Zhang L L and Jia H H 2014 Chin. J. Chem. Phys. 27 75
[28]	Jia H H, Zhao K and Wu X L 2014 Chem. Phys. Lett. 612 151
[29]	Xue L, Fang Z, Li G, Wang H and Jiang H 2011 Sens. Actuator B-Chem. 156 410
[30]	Luo Y, Norman P, Macak P and Ågren H 2000 J. Phys. Chem. A 104 4718
[31]	Olsen J and Jorgensen P 1985 J. Chem. Phys. 82 3235
[32]	Monson P R and McClain W M 1970 J. Chem. Phys. 53 29
[33]	GAUSSIAN 09, References in http://www.gaussian.com/
[34]	DALTON 2013 A molecular electronic structure program, Release Dalton2013.0, see http://daltonprogram.org/
[35]	Kim H M and Cho B R 2009 Acc. Chem. Res. 42 863
[36]	Zhao K, Ferrighi L, Frediani L, Wang C K and Luo Y 2007 J. Chem. Phys. 126 204509

Responsive mechanism and molecular design of di-2-picolylamine-based two-photon fluorescent probes for zinc ions

Responsive mechanism and molecular design of di-2-picolylamine-based two-photon fluorescent probes for zinc ions

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