Journal of Materials Chemistry B
Paper
MHz; DMSO-d6; TMS): 9.10 (4H, d, J ¼ 5.8 Hz, Ar–H ortho to N+),
8.61 (2H, t, J ¼ 7.5 Hz, Ar–H para to N+), 8.16 (4H, t, J ¼ 6.5 Hz,
9 M. De, P. S. Ghosh and V. M. Rotello, Adv. Mater., 2008, 20,
4225.
Ar–H meta to N+), 7.97 (4H, t, J ¼ 6.4 Hz, Ar–H ortho to COO), 10 Z. Zhelev, H. Ohba and R. Bakalova, J. Am. Chem. Soc., 2006,
7.67 (4H, d, J ¼ 8.2 Hz, Ar–H meta to COO), 7.39 (4H, q, J ¼ 8.2
128, 6324.
Hz), 7.22–7.17 (6H, m), 7.07–7.00 (8H, m), 4.59 (4H, t, J ¼ 7.3 Hz, 11 Y. Hong, J. W. Y. Lam and B. Z. Tang, Chem. Soc. Rev., 2011,
CH2OOC), 4.28 (4H, t, J ¼ 6.4 Hz, CH2Br), 1.91 (4H, d, J ¼ 6.5 Hz, 40, 5361.
CH2CH2OOC), 1.71 (4H, t, J ¼ 6.6 Hz, CH2CH2Br), 1.39–1.26 12 R. Zhang, Y. Yuan, J. Liang, R. T. K. Kwok, Q. Zhu, G. Feng,
(28H, m, CH2(CH2)7CH2CH2Br); MS (ESI) m/z: [M ꢁ 2Br]2+ calcd:
J. Geng, B. Z. Tang and B. Liu, ACS Appl. Mater. Interfaces,
2014, 6, 14302.
542.305; found: 542.308.
13 F. Wang, W. B. Tan, Y. Zhang, X. Fan and M. Wang,
Nanotechnology, 2006, 17, R1.
14 Y. G. Yanushevicha, D. B. Staroverova, A. P. Savitskyb,
A. F. Fradkova, N. G. Gurskayaa, M. E. Bulinaa,
K. A. Lukyanova and S. A. Lukyanova, FEBS Lett., 2002, 511,
11.
Conclusions
Through the marriage of the AIE effect and self-assembly of
bolaamphiphiles, mono-molecule layered nanostructures with
good uorescent emission properties have been achieved. It has
been proven that the assemblies formed in the aqueous solu- 15 Y. Su, M. Hu, C. Fan, Y. He, Q. Li, W. Li, L.-h. Wang, P. Shen
tion have two distinct mophologies depending on concentra- and Q. Huang, Biomaterials, 2010, 31, 4829.
tion, and both are stable against the dewetting process. Due to 16 Y. Hong, J. W. Y. Lam and B. Z. Tang, Chem. Commun., 2009,
the AIE effect, the self-assembled nanostructures emit strong 4332.
green light and show a quantum yield as high as 15%. More 17 R. D. Moriarty, A. Martin, K. Adamson, E. O'Reilly,
importantly, the nano-uorogens can label HeLa cells without
the assistance of any matrix and can be successfully used to
P. Mollard, R. J. Forster and T. E. Keyes, J. Microsc., 2014,
253, 204.
map the cell image by uorescence. This work opens a novel 18 J. Luo, Z. Xie, J. W. Y. Lam, L. Cheng, H. Chen, C. Qiu,
avenue to fabricate water-soluble and biocompatible nano-
uorogens by self-assembly, and it is anticipated that it will be
H. S. Kwok, X. Zhan, Y. Liu, D. Zhu and B. Z. Tang, Chem.
Commun., 2001, 1740.
extended to other AIE dyes and other bio-related detection 19 Y. Dong, J. W. Y. Lam, A. Qin, J. Liu, Z. Li, B. Z. Tang, J. Sun
systems.
and H. S. Kwok, Appl. Phys. Lett., 2007, 91, 011111.
20 A. Qin, C. K. W. Jim, Y. Tang, J. W. Y. Lam, J. Liu, F. Mahtab,
P. Gao and B. Z. Tang, J. Phys. Chem. B, 2008, 112, 9281.
21 S. Chen, J. Liu, Y. Liu, H. Su, Y. Hong, C. K. W. Jim,
R. T. K. Kwok, N. Zhao, W. Qin, J. W. Y. Lam, K. S. Wong
and B. Z. Tang, Chem. Sci., 2012, 3, 1804.
Acknowledgements
The authors are indebted to Prof. L. Z. Fan and Mr Z. T. Fan for
helping us in contacting the cell imaging measurements. We
would like to thank the National Natural Science Foundation of 22 B.-K. An, S.-K. Kwon, S.-D. Jung and S. Y. Park, J. Am. Chem.
China (91127032, 21174035, 21274034, 21204054, 21233003), a
Soc., 2002, 124, 14410.
Project Funded by the Priority Academic Program Development 23 C. J. Bhongale, C.-W. Chang, C.-S. Lee, E. W.-G. Diau and
of Jiangsu Higher Education Institutions Excellent Young C.-S. Hsu, J. Phys. Chem. B, 2005, 109, 13472.
Teachers in Zhejiang Province and Hangzhou Normal Univer- 24 M. Han and M. Hara, J. Am. Chem. Soc., 2005, 127, 10951.
sity (HNUEYT 2011-01-019) for nancial support.
25 Y. Qian, S. Li, G. Zhang, Q. Wang, S. Wang, H. Xu, C. Li, Y. Li
and G. Yang, J. Phys. Chem. B, 2007, 111, 5861.
26 Y.-T. Wu, M.-Y. Kuo, Y.-T. Chang, C.-C. Shin, T.-C. Wu,
C.-C. Tai, T.-H. Cheng and W.-S. Liu, Angew. Chem., Int.
Ed., 2008, 47, 9891.
Notes and references
1 M. Zhang, L. Bai, W. Shang, W. Xie, H. Ma, Y. Fu, D. Fang,
H. Sun, L. Fan, M. Han, C. Liu and S. Yang, J. Mater. 27 C.-X. Yuan, X.-T. Tao, L. Wang, J.-X. Yang and M.-H. Jiang, J.
Chem., 2012, 22, 7461.
Phys. Chem. C, 2009, 113, 6809.
2 D. Ding, K. Li, B. Liu and B. Z. Tang, Acc. Chem. Res., 2013, 46, 28 M. Wang, G. Zhang, D. Zhang, D. Zhu and B. Z. Tang, J.
2441. Mater. Chem., 2010, 20, 1858.
3 Y. Liu, Z. Wang, G. Zhang, W. Zhang, D. Zhang and X. Jiang, 29 Y. Hong, L. Meng, S. Chen, C. W. T. Leung, L.-T. Da,
Analyst, 2012, 137, 4654.
4 X. Wang, J. Hu, G. Zhang and S. Liu, J. Am. Chem. Soc., 2014,
136, 9890.
M. Faisal, D.-A. Silva, J. Liu, J. W. Y. Lam, X. Huang and
B. Z. Tang, J. Am. Chem. Soc., 2011, 134, 1680.
30 M. Faisal, Y. Hong, J. Liu, Y. Yu, J. W. Lam, A. Qin, P. Lu and
B. Z. Tang, Chemistry, 2010, 16, 4266.
5 X. Shen, G. Zhang and D. Zhang, Org. Lett., 2012, 14, 1744.
6 X. Feng, L. Liu, S. Wang and D. Zhu, Chem. Soc. Rev., 2010, 31 D. Ding, K. Li, W. Qin, R. Zhan, Y. Hu, J. Liu, B. Z. Tang and
39, 2411. B. Liu, Adv. Healthcare Mater., 2013, 2, 500.
7 X. Mei, D. Chen, N. Li, Q. Xu, J. Ge, H. Li, B. Yang, Y. Xu and 32 G. Wang, R. Zhang, C. Xu, R. Zhou, J. Dong, H. Bai and
J. Lu, So Matter, 2012, 8, 5309.
X. Zhan, ACS Appl. Mater. Interfaces, 2014, 6, 11136.
8 Y. Yu, C. Feng, Y. Hong, J. Liu, S. Chen, K. M. Ng, K. Q. Luo
and B. Z. Tang, Adv. Mater., 2011, 23, 3298.
J. Mater. Chem. B
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