Selective detection of phosphaphenanthrene-containing luminophors with aggregation-induced emission enhancement to transition metal ions

doi:10.1007/s11458-011-0221-1

Front Chem Chin

2011, Vol. 6

Issue (1) : 15-20 https://doi.org/10.1007/s11458-011-0221-1

RESEARCH ARTICLE

Selective detection of phosphaphenanthrene-containing luminophors with aggregation-induced emission enhancement to transition metal ions

Lijun QIAN^1,2, Bin TONG¹, Shu SUN¹, Jianbing SHI¹(

), Junge ZHI³, Yuping DONG¹(

)

1. College of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, China.; 2. Department of Materials Science and Engineering, Beijing Technology and Business University, Beijing 100037, China; 3. College of Science, Beijing Institute of Technology, Beijing 100081, China

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Abstract

Transition metal ions (Pb²⁺, Zn²⁺, Cd²⁺, Co²⁺, Mn²⁺, Cu²⁺, Ni²⁺, Hg²⁺, Ag⁺, Fe³⁺) in water are used to quench emission of 2-(6-oxido-6H-dibenz<c,e><1,2>oxaphosphorin-6-yl)-1,4-phenylene-bis(p-pentyloxylbenzoate)s (MD5) with aggregation-induced emission enhancement (AIEE) in water-acetonitrile (AN) mixture (80:20 by volume). Among all metal ions, Fe³⁺ exhibits the highest quenching efficiency on AIEE of MD5 even when the concentration of Fe³⁺ is lower than 1×10^-6 mol/L. The quenching efficiency of Hg²⁺ is lower than that of Fe³⁺ at the same concentration, though MD5 is used to detect Hg²⁺ efficiently, too. To other metal ions, low quenching efficiency has few relations with a wider concentration range. The UV absorbance spectra show only red shift of absorbance wavelength in the presence of Hg²⁺ and Fe³⁺, which indicates a salt-induced J-aggregation. SEM photos reveal larger aggregation and morphological change of nanoparticles of MD5 in water containing Hg²⁺ and Fe³⁺, which reduce the surface area of MD5 emission for further aggregation. The selective quenching effect of transition metal ions to emission of MD5 has a potential application in chemical sensors of some metal ions.

Keywords AIEE phosphaphenanthrene transition metal ions quenching effect

Corresponding Author(s): SHI Jianbing,Email:bing@bit.edu.cn; DONG Yuping,Email:chdongyp@bit.edu.cn

Issue Date: 05 March 2011

Cite this article:

Lijun QIAN,Bin TONG,Shu SUN, et al. Selective detection of phosphaphenanthrene-containing luminophors with aggregation-induced emission enhancement to transition metal ions[J]. Front Chem Chin, 2011, 6(1): 15-20.

URL:

https://academic.hep.com.cn/fcc/EN/10.1007/s11458-011-0221-1
https://academic.hep.com.cn/fcc/EN/Y2011/V6/I1/15

Fig.1 PL spectra of in water-AN mixture (80∶20 by volume) solution in the presence of different transition metal ions in water. Excitation wavelength: 275 nm. Concentration of metal ions was 1 × 10 mol/L.

Fig.2 Relative quenching efficiency of ten transitional metal ions on emission of aggregated in water-AN mixture (80∶20 by volume) solution.

Fig.3 PL spectra of in the presence of (a) Fe and (b) Hg in water-AN mixture (80∶20 by volume) (the concentrations of metal ions (mol/L): 0, 1×10, 1×10, 1×10, 1×10). Excitation wavelength: 275 nm.

Fig.4 Relation between quenching efficiency of Fe, Hg, Cu on emission and concentration of metal ions in water-AN mixture (80∶20 by volume).

Fig.5 UV absorbance curves of in water-AN mixture (80∶20 by volume) in the presence of transition metal ions. Transition metal ions concentration: 1 × 10 mol/L.

Fig.6 SEM photos of aggregates in water-AN mixture (80∶20 by volume) in the presence of 1 × 10 mol/L metal ions. The sequence of metal ions are (a) no, (b) Cu, (c) Hg and (d) Fe.

Fig.7 The surface element analysis of aggregated particles in the presence of Hg by EDS.

1	de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E., Chem. Rev. 1997, 97, 1515–1566 doi: 10.1021/cr960386p pmid:11851458
2	Liu, J.; Lu, Y., J. Am. Chem. Soc. 2003, 125, 6642–6643 doi: 10.1021/ja034775u pmid:12769568
3	Peng, X.; Du, J.; Fan, J.; Wang, J.; Wu, Y.; Zhao, J.; Sun, S.; Xu, T., J. Am. Chem. Soc. 2007, 129, 1500–1501 doi: 10.1021/ja0643319 pmid:17283986
4	Royzen, M.; Dai, Z.; Canary, J. W., J. Am. Chem. Soc. 2005, 127, 1612–1613 doi: 10.1021/ja0431051 pmid:15700975
5	Mandal, A. K.; Suresh, M.; Suresh, E.; Mishra, S. K.; Mishra, S.; Das, A., Sens. Actuators B Chem. 2010, 145, 32–38 doi: 10.1016/j.snb.2009.11.016
6	Kim, I. B.; Erdogan, B.; Wilson, J. N.; Bunz, U. H. F., Chemistry 2004, 10, 6247–6254 doi: 10.1002/chem.200400788 pmid:15526311
7	Ono, A.; Togashi, H., Angew. Chem. Int. Ed. 2004, 43, 4300–4302 doi: 10.1002/anie.200454172
8	Moon, S. Y.; Youn, N. J.; Park, S. M.; Chang, S. K., J. Org. Chem. 2005, 70, 2394–2397 doi: 10.1021/jo0482054 pmid:15760241
9	Descalzo, A.; Martò′nez-Manez, R.; Radeglia, R.; Rurack, K.; Soto, J., J. Am. Chem. Soc. 2003, 125, 3418–3419 doi: 10.1021/ja0290779 pmid:12643689
10	Guo, X. F.; Qian, X. H.; Jia, L. H., J. Am. Chem. Soc. 2004, 126, 2272–2273 doi: 10.1021/ja037604y pmid:14982408
11	Zhang, H.; Han, L. F.; Zachariasse, K. A.; Jiang, Y. B., Org. Lett. 2005, 7, 4217–4220 doi: 10.1021/ol051614h pmid:16146391
12	Yoon, S.; Miller, E. W.; He, Q.; Do, P. H.; Chang, C. J., Angew. Chem. Int. Ed. 2007, 46, 6658–6661 doi: 10.1002/anie.200701785
13	Bricks, J. L.; Kovalchuk, A.; Trieflinger, C.; Nofz, M.; Büschel, M.; Tolmachev, A. I.; Daub, J.; Rurack, K., J. Am. Chem. Soc. 2005, 127, 13522–13529 doi: 10.1021/ja050652t pmid:16190715
14	Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z., Chem. Commun. 2001, 1740–1741 doi: 10.1039/b105159h pmid:12240292
15	Bhongale, C. J.; Hsu, C. S., Angew. Chem. Int. Ed. 2006, 45, 1404–1408 doi: 10.1002/anie.200503067
16	Chung, J. W.; An, B. K.; Park, S. Y., Chem. Mater. 2008, 20, 6750–6755 doi: 10.1021/cm8019186
17	An, B. K.; Lee, D. S.; Lee, J. S.; Park, Y. S.; Song, H. S.; Park, S. Y., J. Am. Chem. Soc. 2004, 126, 10232–10233 doi: 10.1021/ja046215g pmid:15315421
18	Qin, A.; Jim, C. K. W.; Tang, Y.; Lam, J. W. Y.; Liu, J.; Mahtab, F.; Gao, P.; Tang, B. Z., J. Phys. Chem. B 2008, 112, 9281–9288 doi: 10.1021/jp800296t pmid:18630853
19	Palayangoda, S. S.; Cai, X.; Adhikari, R. M.; Neckers, D. C., Org. Lett. 2008, 10, 281–284 doi: 10.1021/ol702666g pmid:18092792
20	Hong, Y. N.; Lam, J. W. Y.; Tang, B. Z., Chem. Commun. 2009, 4332–4353 doi: 10.1039/b904665h pmid:19597589
21	Liu, Y.; Tao, X.; Wang, F.; Dang, X.; Zou, D.; Ren, Y.; Jiang, M., J. Phys. Chem. C 2008, 112, 3975–3981 doi: 10.1021/jp7117373
22	Wu, Y. T.; Kuo, M. Y.; Chang, Y. T.; Shin, C. C.; Wu, T. C.; Tai, C. C.; Cheng, T. H.; Liu, W. S., Angew. Chem. Int. Ed. 2008, 47, 1–5 doi: 10.1002/anie.200790254
23	Zeng, Q.; Li, Z.; Dong, Y.; Di, C.; Qin, A.; Hong, Y.; Ji, L.; Zhu, Z.; Jim, C. K.; Yu, G.; Li, Q.; Li, Z.; Liu, Y.; Qin, J.; Tang, B. Z., Chem. Commun. 2007, 70–72 doi: 10.1039/b613522f pmid:17279264
24	Dong, Y.; Lam, J. W. Y.; Qin, A.; Sun, J.; Liu, J.; Li, Z.; Sun, J.; Sung, H. H. Y.; Williams, I. D.; Kwok, H. S.; Tang, B. Z., Chem. Commun. 2007, 3255–3257 doi: 10.1039/b704794k pmid:17668092
25	Tong, H.; Hong, Y.; Dong, Y.; H?ussler, M.; Li, Z.; Lam, J. W. Y.; Dong, Y.; Sung, H. H. Y.; Williams, I. D.; Tang, B. Z., J. Phys. Chem. B 2007, 111, 11817–11823 doi: 10.1021/jp073147m pmid:17877385
26	Tong, H.; Hong, Y.; Dong, Y.; H?ussler, M.; Lam, J. W. Y.; Li, Z.; Guo, Z.; Guo, Z.; Tang, B. Z., Chem. Commun. 2006, 3705–3707 doi: 10.1039/b608425g pmid:17047818
27	Qian, L. J.; Tong, B.; Zhi, J. G.; Yang, F.; Shen, J. B.; Shi, J. B.; Dong, Y. P., Acta Chimi. Sin. 2008, 66, 1134–1138
28	Hong, Y.; H?ussler, M.; Lam, J. W. Y.; Li, Z.; Sin, K. K.; Dong, Y.; Tong, H.; Liu, J.; Qin, A.; Renneberg, R.; Tang, B. Z., Chemistry 2008, 14, 6428–6437 doi: 10.1002/chem.200701723 pmid:18512826
29	An, B. K.; Kwon, S. K.; Jung, S. D.; Park, S. Y., J. Am. Chem. Soc. 2002, 124, 14410–14415 doi: 10.1021/ja0269082 pmid:12452716
30	Itami, K.; Yoshida, J., Chemistry 2006, 12, 3966–3974 doi: 10.1002/chem.200500958 pmid:16380951
31	Yang, J.; Aschemeyer, S.; Martinez, H. P.; Trogler, W. C., Chem. Commun. 2010, 46, 6804–6806 doi: 10.1039/c0cc01906b pmid:20737079
32	Qin, A. J.; Lam, J. W. Y.; Tang, L.; Jim, C. K. W.; Zhao, H.; Sun, J. Z.; Tang, B. Z., Macromolecules 2009, 42, 1421–1424 doi: 10.1021/ma8024706
33	Liu, L.; Zhang, G. X.; Xiang, J. F.; Zhang, D. Q.; Zhu, D. B., Org. Lett. 2008, 10, 4581–4584 doi: 10.1021/ol801855s pmid:18785747
34	Qian, L. J.; Tong, B.; Shen, J. B.; Shi, J. B.; Zhi, J. G.; Dong, Y. Q.; Yang, F.; Dong, Y. P.; Lam, J. W. Y.; Liu, Y.; Tang, B. Z., J. Phys. Chem. B 2009, 113, 9098–9103 doi: 10.1021/jp900665x pmid:19522490
35	Lu, L. D.; Helgeson, R.; Jones, R. M.; McBranch, D.; Whitten, D., J. Am. Chem. Soc. 2002, 124, 483–488 doi: 10.1021/ja011517t pmid:11792220
36	Saito, K., J. Phys. Chem. B 2001, 105, 4235–4238 doi: 10.1021/jp003141w
37	Shankar, S. S.; Patil, U. S.; Prasad, B. L. V.; Sastry, M., Langmuir 2004, 20, 8853–8857 doi: 10.1021/la0495837 pmid:15379517
38	Henglein, A.; Brancewica, C., Chem. Mater. 1997, 9, 2164–2167 doi: 10.1021/cm970258x

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