Citation: PENG Yu-Xin, GAN Yi-Tao, Tao TAO, QIAN Hui-Fen, HUANG Wei. 5, 6-Alkoxyl Protected and 3-/3, 8-Triphenylamine Extended 1, 10-Phenanthroline Derivatives and Their Selective Silver Ion Recognition[J]. Chinese Journal of Inorganic Chemistry, ;2017, 33(11): 2075-2082. doi: 10.11862/CJIC.2017.252 shu

5, 6-Alkoxyl Protected and 3-/3, 8-Triphenylamine Extended 1, 10-Phenanthroline Derivatives and Their Selective Silver Ion Recognition

PENG Yu-Xin ^1,2 ,
GAN Yi-Tao ³ ,
Tao TAO ³ ,
QIAN Hui-Fen ^1,2,, ,
HUANG Wei ^2,,

1.
College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 210009, China
2.
State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China
3.
Collaborative Innovation Center of Atmospheric Environment and Equipment Technology, School of Environmental Science and Engineering, Nanjing University of Information Science & Technology, Nanjing 210044, China

Corresponding author: QIAN Hui-Fen, qhf@njtech.edu.cn HUANG Wei, whuang@nju.edu.cn
Received Date: 13 September 2017
Revised Date: 21 September 2017

Figures(5)

The introduction of alkoxyl groups to 5, 6-positions of 1, 10-phenanthroline can not only lead to the enhancement of the reaction activity, but also increase the solubility of the targeted compounds. Crystal structure analyses reveal that the two alkoxyl groups at 5, 6-positions of 1, 10-phenanthroline adopt double six-membered ethylenedioxy cyclic conformation. Both TPA1 and TPA2 show selective recognition toward the silver ion. No obvious fluorescence quenching is found after the treatment of TPA1 and Ag⁺, in which a red shift of 47 nm in the fluorescence emission spectrum is observed. On the other hand, the two emission peaks at 415 and 542 nm in the fluorescence emission spectra are quenched when TPA2 is reacted with Ag⁺. However, the fluorescence quenching effect for Ag⁺ is not obvious in the case of TPA3, which makes it not a good candidate for the metal-ion recognition.
- triphenylamine,
- 1, 10-phenanthroline,
- crystal structure,
- ion recognition
1. [1]
  Daniel C, Gourlaouen C. Coord. Chem. Rev., 2017, 344:131-149 doi: 10.1016/j.ccr.2016.10.010
2. [2]
  (a) Han H B, Cui R Z, Jing Y M, et al. J. Mater. Chem. C, 2017, 5:8150-8159
  (b)Wei X F, Tan W Y, Zou J H, et al. J. Mater. Chem. C, 2017, 5:2329-2336
3. [3]
  Wu Y Y, Wang P, Wang Y H, et al. J. Mater. Chem. A, 2013, 1:9862-9868 doi: 10.1039/c3ta11571b
4. [4]
  (a) Jiang L, Chen W C, Zheng J W, et al. ACS Appl. Mat. Interfaces, 2017, 9:26958-26964
  (b)Gavriluta A, Fix T, Nonat A, et al. J. Mater. Chem. A, 2017, 5:14031-14040
5. [5]
  Bai Z P, Gao Y N, Zhu P H, et al. Inorg. Chem., 2010, 49: 9005-9011 doi: 10.1021/ic101362y
6. [6]
  (a) Shi S, Liu J, Yao T M, et al. Inorg. Chem., 2008, 47:2910-2912
  (b)Ren P P, Wang R J, Pu S Z, et al. J. Phys. Org. Chem., 2014, 27:183-190
  (c)Batista R M F, Costa S P G, Belsley M, et al. Dyes Pigm., 2009, 80:329-336
7. [7]
  (a) Collin J P, Kayhanian R, Sauvage J P, et al. Chem. Commun., 1997:775-776
  (b)Yang P J, Yang X J, Wu B. Eur. J. Inorg. Chem., 2009: 2951-2958
  (c)Peng Y X, Wang N, Dai Y, et al. RSC Adv., 2015, 5:6395-6406
  (d)Batista R M F, Costa S P G, Lodeiro C, et al. Tetrahedron, 2008, 64:9230-9238
  (e)Kassio P S Z, Neyde Y M I. Dalton Trans., 2017, 46:9951-9958
8. [8]
  Wang X Xu, Tao T, Geng J, et al. Chem. Asian J., 2014, 9: 514-525 doi: 10.1002/asia.201301284
9. [9]
  (a) Tao Y T, Wang Q, Ao L, et al. J. Phys. Chem. C, 2010, 114:601-609
  (b)Usta H, Sheets W S, Denti M, et al. Chem. Mater., 2014, 26:6542-6556
10. [10]
  Peng Y X, Xu D, Wang N, et al. Tetrahedron, 2016, 72:3443-3453 doi: 10.1016/j.tet.2016.04.061
11. [11]
  (a) Bodige S, MacDonnell F M. Tetrahedron Lett., 1997, 38: 8159-8160
  (b)Liu X Q, Zhou X, Shu X, et al. Macromolecules, 2009, 42:7634-7637
  (c)Liu Y, Wang Y F, Guo H P, et al. J. Phys. Chem. C, 2011, 115:4209-4216
12. [12]
  (a) SAINT Ver. 4, Software Reference Manual. Madison: Siemens Analytical X-Ray Systems, 2000.
  (b)Sheldrick G M. SADABS, Program for Empirical Absorp-tion Correction of Area Detector Data, University of Göttingen, Germany, 2000.
  (c)SHELXTL Ver. 6.10, Reference Manual. Madison: Siemens Analytical X-Ray Systems, 2000.
13. [13]
  Ritter K, Pehlken C, Sorsche D, et al. Dalton Trans., 2015, 44:8889-8905 doi: 10.1039/C5DT00214A
14. [14]
  (a) Estrada L A, Neckers D C. Org. Lett., 2011, 13:3304-3307
  (b)Shirai Y, Osgood A J, Zhao Y, et al. J. Am. Chem. Soc., 2006, 128:4854-4864
15. [15]
  (a) Roquet S, Cravino A, Leriche P O, et al. J. Am. Chem. Soc., 2006, 128:3459-3466
  (b)Mikroyannidis J A, Kabanakis A N, Sharma S S, et al. Org. Electron., 2011, 12:774-784
  (c)Shen P, Sang G Y, Lu J J, et al. Macromolecules, 2008, 41:5716-5722
16. [16]
  (a) Batey H D, Whitwood A C, Duhme-Klair A K, et al. Inorg. Chem., 2007, 46:6516-6528
  (b)Shin D H. Ind. Eng. Chem. Res., 2006, 45:656-662
  (c)Engel Y, Dahan A, Rozenshine-Kemelmakher E, et al. J. Org. Chem., 2007, 72:2318-2328
17. [17]
  (a) Mandal S, Ghosh S, Banerjee C, et al. J. Phys. Chem. B, 2013, 117:12212-12223
  (b)Elmes R B P, Turner P, Jolliffe K A. Org. Lett., 2013, 15: 5638-5641
  (c)Wang J F, Chu Q H, Liu X M, et al. J. Phys. Chem. B, 2013, 117:4127-4133
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