Citation: Cao Liang, Xiong Jinfeng, Wu Yancheng, Ding Sha, Li Mingbing, Xie Fen, Ma Zhihan, Wang Zhaoyang. Progress in the Molecular Design and Synthesis of Organic Fluorescent Probe for Picric Acid Detection[J]. Chinese Journal of Organic Chemistry, ;2016, 36(9): 2053-2074. doi: 10.6023/cjoc201604002 shu

Progress in the Molecular Design and Synthesis of Organic Fluorescent Probe for Picric Acid Detection

Cao Liang ^a ,
Xiong Jinfeng ^b ,
Wu Yancheng ^a ,
Ding Sha ^a ,
Li Mingbing ^a ,
Xie Fen ^a ,
Ma Zhihan ^a ,
Wang Zhaoyang ^a,*,,

a.
Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou 510006
b.
HEC Pharm R & D Center, Dongguan 523871

Corresponding author: Wang Zhaoyang, wangzy@scnu.edu.cn
Received Date: 1 April 2016
Revised Date: 26 April 2016

Fund Project: the Guangzhou Science and Technology Project Scientific Special 201607010251Project supported by the Natural Science Foundation of Guangdong Province 2014A030313429the Undergraduates Innovation Project of South China Normal University 20161528

Figures(25)

Highly selective and sensitive detection of nitro aromatic explosive picric acid (PA) has become a challenging task due to the increasing concerns over national security and environmental awareness. In order to adjust to the trend of green chemistry, more and more attention has been attached to the fluorescent probes among various PA detection techniques, especially the organic molecule fluorescent probes without any metal ion (e.g. Hg²⁺)-assisted fluorescence enhancement for their easy availability and good processability. According to the molecular composition of the probes, these organic molecule probes can be classified into three categories as polymer, oligomer, and small molecule type. The progress on their molecular design and synthesis is reviewed, and their future trend is also prospected.
- picric acid,
- organic fluorescent probe,
- molecular design,
- synthesis,
- detection mechanism
1. [1]
  Salinas, Y.; Martinez-Manez, R.; Marcos, M. D.; Sancenon, F.; Costero, A. M.; Parra, M.; Gil, S. Chem. Soc. Rev. 2012, 41, 1261. doi: 10.1039/C1CS15173H
2. [2]
  Shanmugaraju, S.; Mukherjee, P. S. Chem. Commun. 2015, 51, 16014. doi: 10.1039/C5CC07513K
3. [3]
  Germain, M. E.; Knapp, M. J. Chem. Soc. Rev. 2009, 38, 2543. doi: 10.1039/b809631g
4. [4]
  Wei, W.; Lu, R.-J.; Tang, S.-Y.; Liu, X.-Y. J. Mater. Chem. A 2015, 3, 4604. doi: 10.1039/C4TA06828A
5. [5]
  Sun, X.-C.; Wang, Y.; Lei, Y. Chem. Soc. Rev. 2015, 44, 8019. doi: 10.1039/C5CS00496A
6. [6]
  Zyryanov, G. V.; Kopchuk, D. S.; Kovalev, I. S.; Nosova, E. V.; Rusinov, V. L.; Chupakhin, O. N. Russ. Chem. Rev. 2014, 83, 783. doi: 10.1070/RC2014v083n09ABEH004467
7. [7]
  Hu, Z.-C.; Deibert, B.-J.; Li, J. Chem. Soc. Rev. 2014, 43, 5815. doi: 10.1039/C4CS00010B
8. [8]
  Kartha, K. K.; Sandeep, A.; Praveen, V. K.; Ajayaghosh, A. Chem. Rec. 2015, 15, 252. doi: 10.1002/tcr.201402063
9. [9]
  Shanmugaraju, S.; Mukherjee, P. S. Chem. Eur. J. 2015, 21, 6656. doi: 10.1002/chem.201406092
10. [10]
  Zhou, Q.; Swager T. M. J. Am. Chem. Soc. 1995, 117, 7017. doi: 10.1021/ja00131a031
11. [11]
  Swager, T. M. Acc. Chem. Res. 1998, 31, 201. doi: 10.1021/ar9600502
12. [12]
  Yang, J. S.; Swager, T. M. J. Am. Chem. Soc. 1998, 120, 5321. doi: 10.1021/ja9742996
13. [13]
  Yang, J. S.; Swager, T. M. J. Am. Chem. Soc. 1998, 120, 11864. doi: 10.1021/ja982293q
14. [14]
  Ferrand, Y.; Crump, M. P.; Davis, A. P. Science 2007, 318, 619. doi: 10.1126/science.1148735
15. [15]
  He, G.; Peng, H.-N.; Liu, T.-H.; Yang, M.-N.; Zhang, Y.; Fang, Y. J. Mater. Chem. 2009, 19, 7347. doi: 10.1039/b906946a
16. [16]
  Sohn, H.; Calhoun, R. M.; Sailor, M. J.; Trogler, W. C. Angew. Chem., Int. Ed. 2001, 40, 2104. doi: 10.1002/1521-3773(20010601)40:11<>1.0.CO;2-Q
17. [17]
  Sohn, H.; Sailor, M. J.; Magde, D.; Trogler, W. C. J. Am. Chem. Soc. 2003, 125, 3821. doi: 10.1021/ja021214e
18. [18]
  Sanchez, J. C.; DiPasquale, A. G.; Rheingold, A. L.; Trogler, W. C. Chem. Mater. 2007, 19, 6459. doi: 10.1021/cm702299g
19. [19]
  Toal, S. J.; Sanchez, J. C.; Dugan, R. E.; Trogler, W. C. J. Forensic. Sci. 2007, 52, 79. doi: 10.1111/jfo.2007.52.issue-1
20. [20]
  Sanchez, J. C.; Urbas, S. A.; Toal, S. J.; DiPasquale, A. G.; Rheingold, A. L.; Trogler, W. C. Macromolecules 2008, 41, 1237. doi: 10.1021/ma702274c
21. [21]
  Sanchez, J. C.; Trogler, W. C. J. Mater. Chem. 2008, 18, 3143. doi: 10.1039/b802623h
22. [22]
  Martinez, H. P.; Grant, C. D.; Reynolds, J. G.; Trogler, W. C. J. Mater. Chem. 2012, 22, 2908. doi: 10.1039/C2JM15214B
23. [23]
  Dedeoglu, B.; Monari, A.; Etienne, T.; Aviyente, V.; Ozen, A. S. J. Phys. Chem. C 2014, 118, 23946. doi: 10.1021/jp505025t
24. [24]
  Luo, J.-D.; Xie, Z.-L.; Lam, J. W. Y.; Cheng, L.; Chen, H.-Y.; Qiu, C.-F.; Kwok, H. S.; Zhan, X.-W.; Liu, Y.-Q.; Zhu, D.-B.; Tang, B.-Z. Chem. Commun. 2001, 1740.
25. [25]
  Liu, J.-Z.; Zhong, Y.-C.; Lu, P.; Hong, Y.-N.; Lam, J. W. Y.; Faisal, M; Yu, Y.; Wong, K. S.; Tang, B.-Z. Polym. Chem. 2010, 1, 426. doi: 10.1039/c0py00046a
26. [26]
  Zhao, Z.-J.; Jiang, T.; Guo, Y.-J.; Ding, L.-Y.; He, B.-R.; Chang, Z.-F.; Lam, J. W. Y. Liu, J.-Z.; Chan, C. Y. K.; Lu, P. J. Polym. Sci. Part A:Polym. Chem. 2012, 50, 2265. doi: 10.1002/pola.v50.11
27. [27]
  Liu, J.-Z.; Zhong, Y.-C.; Lam, J. W. Y.; Lu, P.; Hong, Y.-N.; Yu, Y.; Yue, Y.-N.; Faisal, M.; Sung, H. H. Y.; Williams, I. D.; Wong K. S.; Tang, B.-Z. Macromolecules 2010, 43, 4921. doi: 10.1021/ma902432m
28. [28]
  Shu, W.-F.; Guan, C.-W.; Guo, W.-H.; Wang, C.-Y.; Shen, Y.-J. J. Mater. Chem. 2012, 22, 3075. doi: 10.1039/c1jm15535k
29. [29]
  Zhang, L.-H.; Jian, T.; Wu, L.-B.; Wan, J.-H.; Chen, C.-H.; Pei, Y.-B.; Lu, H.; Deng, Y.; Bian, G.-F.; Qiu, H.-Y.; Lai, G-Q. Chem. Asian J. 2012, 7, 1583. doi: 10.1002/asia.201200070
30. [30]
  Qu, H.-M.; Jiang, L.-L.; Chen, T.; Tang, J.-K. Chin. J. Org. Chem. 2014, 34, 1061(in Chinese). doi: 10.6023/cjoc201312008
31. [31]
  Das, S.; Chatterjee, D. P.; Samanta, S.; Nandi, A. K. RSC Adv. 2013, 3, 17540. doi: 10.1039/c3ra42479k
32. [32]
  Das, S.; Chatterjee, D. P.; Nandi, A. K. Polym Int. 2014, 63, 2091. doi: 10.1002/pi.2014.63.issue-12
33. [33]
  Laurenti, M.; Lopez-Cabarcos, E.; Garcia-Blanco, F.; Frick, B.; Rubio-Retama, J. Langmuir 2009, 25, 9579. doi: 10.1021/la900864a
34. [34]
  Long, Y.-Y.; Chen, H.-B.; Wang, H.-M.; Peng, Z.; Yang, Y.-F.; Zhang, G.-Q.; Li, N.; Liu, F.; Pei, J. Anal. Chim. Acta 2012, 744, 82. doi: 10.1016/j.aca.2012.07.028
35. [35]
  Shaligram, S.; Wadgaonkar, P. P.; Kharul, U. K. J. Mater. Chem. A 2014, 2, 13983. doi: 10.1039/C4TA02766C
36. [36]
  Zhang, W.; Qiu, L.-G.; Yuan, Y.-P.; Xie, A.-J.; Shen, Y.-H.; Zhu, J.-F. J. Hazard. Mater. 2012, 221, 147.
37. [37]
  Liu, F.; Zhang, L.-J.; Xiao, J.-H; Hu, J.; Liu, H.-L. Front. Mater. Sci. China 2010, 4, 158. doi: 10.1007/s11706-010-0018-z
38. [38]
  Sun, L.-B.; Liang, Z.-Q.; Yu, J.-H.; Xu, R.-R. Polym. Chem. 2013, 4, 1932. doi: 10.1039/c2py21034g
39. [39]
  Del Rosso, P. G; Romagnoli, M. J.; Almassio, M. F.; Barbero, C. A.; Garay, R. O. Sens. Actuators, B 2014, 203, 612. doi: 10.1016/j.snb.2014.07.032
40. [40]
  Hussain, S.; Malik, A. H.; Afroz, M. A.; Iyer, P. K. Chem. Commun. 2015, 51, 7207. doi: 10.1039/C5CC02194D
41. [41]
  Zhang, L.-Z.; Zhao, C.-C.; Zhou, J.-P.; Kondo, T. J. Mater. Chem. C 2013, 1, 5756. doi: 10.1039/c3tc30689e
42. [42]
  Zhou, H.; Li, J.-S.; Chua, M.-H.; Yan, H.; Tang, B.-Z.; Xu, J.-W. Polym. Chem. 2014, 5, 5628. doi: 10.1039/C4PY00518J
43. [43]
  Zhang, Y.-R.; Chen, G.; Lin, Y.-L.; Zhao, L.-F.; Yuan, W.-Z.; Lu, P.; Jim, C. K. W; Zhang, Y.-M.; Tang, B.-Z. Polym. Chem. 2015, 6, 97. doi: 10.1039/C4PY01164C
44. [44]
  Yuan, W.-Z.; Zhao, H.; Shen, X.-Y.; Mahtab, F.; Lam, J. W. Y; Sun, J.-Z.; Tang, B.-Z. Macromolecules 2009, 42, 9400. doi: 10.1021/ma9012169
45. [45]
  Lu, P.; Lam, J. W. Y.; Liu, J.-Z.; Jim, C. K. W.; Yuan, W.-Z.; Chan, C. Y. K.; Xie, N.; Hu, Q.; Cheuk, K. K. L.; Tang, B.-Z. Macromolecules 2011, 44, 5977. doi: 10.1021/ma201203w
46. [46]
  Hu, R. R.; Lam, J. W. Y.; Liu, J.-Z.; Sung, H. H. Y.; Williams, I. D.; Yue, Z. N.; Wong, K. S.; Yuen, M. M. F.; Tang, B. Z. Polym. Chem. 2012, 3, 1481. doi: 10.1039/c2py20057k
47. [47]
  Li, J.; Liu, J.-Z.; Lam, J. W. Y.; Tang, B.-Z. RSC Adv. 2013, 3, 8193. doi: 10.1039/c3ra40867a
48. [48]
  Liu, Y.-J.; Gao, M.; Lam, J. W. Y.; Hu, R.-R.; Tang, B.-Z. Macromolecules 2014, 47, 4908. doi: 10.1021/ma501477w
49. [49]
  Xu, B.-W.; Wu, X.-F.; Li, H.-B.; Tong, H.; Wang, L.-X. Macromolecules 2011, 44, 5089. doi: 10.1021/ma201003f
50. [50]
  Ghosh, K. R.; Saha, S. K.; Wang, Z.-Y. Polym. Chem. 2014, 5, 5638. doi: 10.1039/C4PY00673A
51. [51]
  Hu, X.-M.; Chen, Q.; Zhou, D.; Cao, J.; He, Y.-J.; Han, B.-H. Polym. Chem. 2011, 2, 1124. doi: 10.1039/c1py00012h
52. [52]
  Toal, S. J.; Trogler, W. C. J. Mater. Chem. 2006, 16, 2871. doi: 10.1039/b517953j
53. [53]
  Swager, T. M. Acc. Chem. Res. 2008, 41, 1181. doi: 10.1021/ar800107v
54. [54]
  Tournebize, A.; Wong-Wah-Chung, P.; Therias, S.; Bussiere, P. O.; Rivaton, A.; Caron, T.; Serein-Spirau, F.; Lere-Porte, J. P.; Montmeat, P.; Gardette, J. L. Polym. Degrad. Stab. 2012, 97, 1355. doi: 10.1016/j.polymdegradstab.2012.05.026
55. [55]
  Hong, G.-H.; Sun, J.-B.; Qian, C.; Xue, P.-C.; Gong, P.; Zhang, Z.-Q.; Lu, R. J. Mater. Chem. C 2015, 3, 2371. doi: 10.1039/C4TC02782E
56. [56]
  Liu, T.-H.; Ding, L.-P.; He, G.; Yang, Y.; Wang, W.-L.; Fang, Y. ACS Appl. Mater. Interfaces 2011, 3, 1245. doi: 10.1021/am2000592
57. [57]
  Costa, A. I.; Prata, J. V. Sens. Actuators B 2012, 161, 251. doi: 10.1016/j.snb.2011.10.027
58. [58]
  Sam-ang, P.; Raksasorn, D.; Sukwattanasinitt, M.; Rashatasakhon, P. RSC Adv. 2014, 4, 58077. doi: 10.1039/C4RA11407H
59. [59]
  El-Sayed, M. Y.; Refat, M. S. Int. J. Electrochem. Sci. 2014, 9, 6608.
60. [60]
  El-Sayed, M. Y.; Refat, M. S. Spectrochim. Acta, Part A 2015, 137, 1270. doi: 10.1016/j.saa.2014.09.032
61. [61]
  Zhang, F.; Luo, L.; Sun, Y.; Miao, F.-J.; Bi, J.-H.; Tan, S.-L.; Tian, D.-M.; Li, H.-B. Tetrahedron 2013, 69, 9886. doi: 10.1016/j.tet.2013.08.083
62. [62]
  Bandela, A. K.; Bandaru, S.; Rao, C. P. Chem. Eur. J. 2015, 21, 13364. doi: 10.1002/chem.201500787
63. [63]
  Boonkitpatarakul, K.; Yodta, Y.; Niamnont, N.; Sukwattanasinitt, M. RSC Adv. 2015, 5, 33306. doi: 10.1039/C5RA02758F
64. [64]
  Wang, J.; Mei, J.; Yuan, W.-Z.; Lu, P.; Qin, A.-J.; Sun, J.-Z.; Ma, Y.-G.; Tang, B.-Z. J. Mater. Chem. 2011, 21, 4056. doi: 10.1039/c0jm04100a
65. [65]
  Feng, H.-T.; Zheng, Y.-S. Chem. Eur. J. 2014, 20, 195. doi: 10.1002/chem.201302638
66. [66]
  Yan, X.-Z.; Wang, H.-Z.; Hauke, C. E.; Cook, T. R.; Wang, M.; Saha, M. L.; Zhou, Z.-X.; Zhang, M.-M.; Li, X.-P.; Huang, F.-H.; Stang, P. J. J. Am. Chem. Soc. 2015, 137, 15276. doi: 10.1021/jacs.5b10130
67. [67]
  Pramanik, S.; Bhalla, V.; Kumar, M. Anal. Chim. Acta 2013, 793, 99. doi: 10.1016/j.aca.2013.07.023
68. [68]
  Bhalla, V.; Kaur, S.; Vij, V.; Kumar, M. Inorg. Chem. 2013, 52, 4860. doi: 10.1021/ic3023997
69. [69]
  Bhalla, V; Pramanik, S.; Kumar, M. Chem. Commun. 2013, 49, 895. doi: 10.1039/C2CC36872B
70. [70]
  Chopra, R.; Bhalla, V.; Kumar, M.; Kaur, S. RSC Adv. 2015, 5, 24336. doi: 10.1039/C5RA00436E
71. [71]
  Vij, V.; Bhalla, V.; Kumar, M. ACS Appl. Mater. Interfaces 2013, 5, 5373. doi: 10.1021/am401414g
72. [72]
  Kumar, M.; Vij, V.; Bhalla, V. Langmuir 2012, 28, 12417. doi: 10.1021/la302309z
73. [73]
  Kaur, S.; Bhalla, V.; Vij, V.; Kumar, M. J. Mater. Chem. C 2014, 2, 3936. doi: 10.1039/c3tc32516d
74. [74]
  Xie, H.-L.; Wang, H.; Xu, Z.; Qiao, R.-J.; Wang, X.-F.; Wang, X.-M.; Wu, L.-F.; Lu, H.-F.; Feng, S.-Y. J. Mater. Chem. C 2014, 2, 9425. doi: 10.1039/C4TC01183J
75. [75]
  Venkatramaiah, N.; Kumar, S.; Patil, S. Chem. Commun. 2012, 48, 5007. doi: 10.1039/c2cc31606d
76. [76]
  Venkatramaiah, N.; Kumar, S.; Patil, S. Chem. Eur. J. 2012, 18, 14745. doi: 10.1002/chem.201201764
77. [77]
  Kumar, S.; Venkatramaiah, N.; Patil, S. J. Phys. Chem. C 2013, 117, 7236.
78. [78]
  Li, X.-G.; Liao, Y.-Z.; Huang, M.-R.; Strong, V.; Kaner, R. B. Chem. Sci. 2013, 4, 1970. doi: 10.1039/c3sc22107e
79. [79]
  Liao, Y.-Z.; Strong, V.; Wang, Y.; Li, X.-G.; Wang, X.; Kaner, R. B. Adv. Funct. Mater. 2012, 22, 726. doi: 10.1002/adfm.201102013
80. [80]
  Bhalla, V.; Singh, H.; Kumar, M.; Prasad, S. K. Langmuir 2011, 27, 15275. doi: 10.1021/la203774p
81. [81]
  Bhalla, V; Arora, H; Singh, H; Kumar, M. Dalton Trans. 2013, 42, 969. doi: 10.1039/C2DT31459B
82. [82]
  Arora, H.; Bhalla, V.; Kumar, M. RSC Adv. 2015, 5, 32637. doi: 10.1039/C5RA04337A
83. [83]
  Bhalla, V.; Gupta, A.; Kumar, M. Org. Lett. 2012, 14, 3112. doi: 10.1021/ol301202v
84. [84]
  Bhalla, V.; Gupta, A.; Kumar, M.; Rao, D. S. S.; Prasad, S. K. ACS Appl. Mater. Interfaces 2013, 5, 672. doi: 10.1021/am302132h
85. [85]
  Andrew, T. L.; Swager, T. M. J. Am. Chem. Soc. 2007, 129, 7254. doi: 10.1021/ja071911c
86. [86]
  Germain, M. E.; Knapp, M. J. J. Am. Chem. Soc. 2008, 130, 5422. doi: 10.1021/ja800403k
87. [87]
  Lv, X.-J.; Qi, L.; Gao, X.-Y.; Wang, H.; Huo, Y.; Zhang, Z.-Q. Talanta 2016, 150, 319. doi: 10.1016/j.talanta.2015.12.053
88. [88]
  Prasad, K. D.; Row, T. N. G. RSC Adv. 2014, 4, 45306. doi: 10.1039/C4RA06286H
89. [89]
  Yang, H.-X.; Xiang, K.; Li, Y.-M.; Li, S.-H.; Xu, C.-H. J. Organomet. Chem. 2016, 801, 96. doi: 10.1016/j.jorganchem.2015.10.017
90. [90]
  Pati, P. B.; Zade, S. S. Tetrahedron Lett. 2014, 55, 5290. doi: 10.1016/j.tetlet.2014.07.098
91. [91]
  Li, W.-F.; Ma, H.-C.; Lei, Z.-Q. RSC Adv. 2014, 4, 39351. doi: 10.1039/C4RA05843G
92. [92]
  Chowdhury, A.; Mukherjee, P. S. J. Org. Chem. 2015, 80, 4064. doi: 10.1021/acs.joc.5b00348
93. [93]
  Acharyya, K.; Mukherjee, P. S. Chem. Commun. 2014, 50, 15788. doi: 10.1039/C4CC06225F
94. [94]
  Vishnoi, P.; Sen, S.; Patwari, G. N.; Murugavel, R. New J. Chem. 2015, 39, 886. doi: 10.1039/C4NJ01093K
95. [95]
  Roy, B.; Bar, A.-K.; Gole, B.; Mukherjee, P.-S. J. Org. Chem. 2013, 78, 1306. doi: 10.1021/jo302585a
96. [96]
  Kumar, R.; Sandhu, S.; Singh, P.; Hundal, G.; Hundal, M. S.; Kumar, S. Asian J. Org. Chem. 2014, 3, 805. doi: 10.1002/ajoc.v3.7
97. [97]
  Shanmugaraju, S.; Joshi, S. A.; Mukherjee, P. S. J. Mater. Chem. 2011, 21, 9130. doi: 10.1039/c1jm10406c
98. [98]
  Gole, B.; Shanmugaraju, S.; Bar, A. K.; Mukherjee, P. S. Chem. Commun. 2011, 47, 10046. doi: 10.1039/c1cc13925h
99. [99]
  Santra, D. C.; Bera, M. K.; Sukul, P. K.; Malik, S. Chem. Eur. J. 2016, 22, 2012. doi: 10.1002/chem.201504126
100. [100]
  Peng, Y.; Zhang, A.-J.; Dong, M.; Wang, Y.-W. Chem. Commun. 2011, 47, 4505. doi: 10.1039/c1cc10400d
101. [101]
  Udhayakumari, D.; Velmathi, S.; Venkatesan, P.; Wu, S.-P. J. Lumin. 2015, 161, 411. doi: 10.1016/j.jlumin.2015.01.052
102. [102]
  Pandith, A.; Kumar, A.; Lee, J. Y.; Kim, H. S. Tetrahedron Lett. 2015, 56, 7094. doi: 10.1016/j.tetlet.2015.11.017
103. [103]
  Figueira-Duarte, TM.; Mullen, K. Chem. Rev. 2011, 111, 7260. doi: 10.1021/cr100428a
104. [104]
  Mosca, L.; Behzad, S. K.; Anzenbacher, P. J. Am. Chem. Soc. 2015, 137, 7967. doi: 10.1021/jacs.5b04643
105. [105]
  Venkatramaiah, N.; Firmino, A. D. G.; Paz, F. A. A.; Tome, J. P. C. Chem. Commun. 2014, 50, 9683. doi: 10.1039/C4CC03980G
106. [106]
  Gole, B.; Song, W. T.; Lackinger, M.; Mukherjee, P. S. Chem. Eur. J. 2014, 20, 13662. doi: 10.1002/chem.v20.42
107. [107]
  Chopra, R.; Kaur, P.; Singh, K. Anal. Chim. Acta 2015, 864, 55. doi: 10.1016/j.aca.2015.01.029
108. [108]
  Udhayakumari, D.; Velmathi, S.; Venkatesan, P.; Wu, S.-P. Anal. Methods 2015, 7, 1161. doi: 10.1039/C4AY02529F
109. [109]
  Ding, L.-P.; Bai, Y.-M.; Cao, Y.; Ren, G.-J.; Blanchard, G. J.; Fang, Y. Langmuir 2014, 30, 7645. doi: 10.1021/la5011264
110. [110]
  Liu, K.; Liu, T.-H.; Chen, X.-L.; Sun, X.-H.; Fang, Y. ACS Appl. Mater. Interfaces 2013, 5, 9830. doi: 10.1021/am4030774
111. [111]
  Liu, T.-H.; Ding, L.-P.; Zhao, K.-R.; Wang, W.-L.; Fang, Y., J. Mater. Chem. 2012, 22, 1069. doi: 10.1039/C1JM14022A
112. [112]
  Ding, L.-P.; Liu, Y.; Cao, Y.; Wang, L.-L.; Xin, Y.-H.; Fang, Y. J. Mater. Chem. 2012, 22, 11574. doi: 10.1039/c2jm30697b
113. [113]
  Xu, Y.-Q.; Li, B.-H.; Li, W.-W.; Zhao, J.; Sun, S.-G.; Pang, Y. Chem. Commun. 2013, 49, 4764. doi: 10.1039/c3cc41994k
114. [114]
  Tian, X.; Qi, X.-J.; Liu, X.-Y.; Zhang, Q.-H.; Sens. Actuators, B 2016, 229, 520. doi: 10.1016/j.snb.2016.02.016
115. [115]
  He, X.-M.; Zhang, P.; Lin, J.-B.; Huynh, H. V.; Munoz, S. E. N.; Ling, C.-C.; Baumgartner, T. Org. Lett. 2013, 15, 5322. doi: 10.1021/ol402582p
116. [116]
  Ma, Q.-Y.; Guan, R.-F.; Li, G.-Z; Feng, S-Y. Chin. J. Org. Chem. 2011, 31, 1395(in Chinese).
  (马庆宇, 关瑞芳, 李国忠, 冯圣玉.有机化学, 2011, 31, 1395.)
  (b) Li, S.-S.; Leng, T.-H.; Zhong, H.-B.; Wang, C.-Y.; Shen, Y.-J. J. Heterocycl. Chem. 2012, 49, 64.
117. [117]
  Zhao, Y.-F.; Hao, W.-L.; Ma, W.-J.; Zang, Z.-Z.; Zhang, H.-R.; Liu, X.-X.; Zou, S.-F.; Zhang, H.-X.; Liu, W.-C.; Gao, J.-H. New J. Chem. 2014, 38, 5754. doi: 10.1039/C4NJ00913D
118. [118]
  An, Z.-F.; Zheng, C.; Chen, R.-F.; Yin, J.; Xiao, J.-J.; Shi, H.-F.; Tao, Y.; Qian, Y.; Huang, W. Chem. Eur. J. 2012, 18, 15655. doi: 10.1002/chem.201202337
119. [119]
  Dey, N.; Samanta, S. K.; Bhattacharya, S. ACS Appl. Mater. Interfaces 2013, 5, 8394. doi: 10.1021/am401608q
120. [120]
  Wu, Y.-C.; You, J.-Y.; Guan, L.-T.; Shi, J.; Cao, L.; Wang, Z.-Y. Chin. J. Org. Chem. 2015, 35, 2465(in Chinese). doi: 10.6023/cjoc201507022
121. [121]
  Xiong, J.-F.; Luo, S.-H.; Huo, J.-P.; Liu, J.-Y.; Chen, S.-X.; Wang, Z.-Y. J. Org. Chem. 2014, 79, 11619. doi: 10.1021/jo502281b
122. [122]
  Sandhu, S.; Kumar, R.; Singh, P.; Mahajan, A.; Kaur, M.; Kumar, S. ACS Appl. Mater. Interfaces 2015, 7, 10491. doi: 10.1021/acsami.5b01970
123. [123]
  Hu, Y.-J.; Tan, S.-Z.; Shen, G.-L.; Yu, R.-Q. Anal. Chim. Acta 2006, 570, 170. doi: 10.1016/j.aca.2006.04.026
124. [124]
  Venkatesan, N.; Singh, V.; Rajakumar, P.; Mishra, A. K. RSC Adv. 2014, 4, 53484. doi: 10.1039/C4RA06320A
125. [125]
  Madhu, S.; Bandela, A.; Ravikanth, M. RSC Adv. 2014, 4, 7120. doi: 10.1039/c3ra46565a
126. [126]
  Ma, Y.-X.; Li, H.; Peng, S.; Wang, L.-Y. Anal. Chem. 2012, 84, 8415. doi: 10.1021/ac302138c
127. [127]
  Dubey, A.; Mishra, A.; Min, J. W.; Lee, M. H.; Kim, H.; Stang, P. J.; Chi, K. W. Inorg. Chim. Acta 2014, 423, 326. doi: 10.1016/j.ica.2014.08.037
128. [128]
  Bereau, V.; Duhayon, C.; Sutter, J. P. Chem. Commun. 2014, 50, 12061. doi: 10.1039/C4CC05888G
129. [129]
  Swamy, P. C. A; Thilagar, P. Chem. Eur. J. 2015, 21, 8874. doi: 10.1002/chem.201500727
130. [130]
  Kumar, M.; Reja, S. I.; Bhalla, V. Org. Lett. 2012, 14, 6084. doi: 10.1021/ol3029753
131. [131]
  Zhang, J.-R.; Yue, Y.-Y.; Luo, H.-Q.; Li, N.-B. Analyst 2016, 141, 1091. doi: 10.1039/C5AN02251G
132. [132]
  Thomas, S. W.; Joly, G. D.; Swager, T. M. Chem. Rev. 2007, 107, 1339. doi: 10.1021/cr0501339
133. [133]
  Gu, C.; Huang, N.; Wu, Y.; Xu, H.; Jiang, D.-L. Angew. Chem., Int. Ed. 2015, 54, 11540. doi: 10.1002/anie.201504786
134. [134]
  Sun, X.-C.; Liu, Y.-X.; Shaw, G.; Carrier, A.; Dey, S.; Zhao, J.; Lei, Y. ACS Appl. Mater. Interfaces 2015, 7, 13189. doi: 10.1021/acsami.5b03655
135. [135]
  Malik, A. H.; Hussain, S.; Kalita, A.; Iyer, P. K. ACS Appl. Mater. Interfaces 2015, 7, 26968. doi: 10.1021/acsami.5b08068
136. [136]
  Liang, Z.-C.; Chen, H.; Wang, X.-H.; Sun, R.-C. Dyes Pigm. 2016, 125, 367. doi: 10.1016/j.dyepig.2015.10.045
137. [137]
  Wang, D.-H.; Cui, Y.-Z.; Tao, F.-R.; Niu, Q.-F.; Li, T.-D.; Xu, H. Sens. Actuators, B 2016, 225, 319. doi: 10.1016/j.snb.2015.11.038
138. [138]
  Sun, X.-C.; Ma, X.-Y.; Kumar, C. V.; Lei, Y. Anal. Methods 2014, 6, 8464. doi: 10.1039/C4AY01941E
139. [139]
  Pinrat, O.; Boonkitpatarakul, K.; Paisuwan, W.; Sukwattanasinitt, M.; Ajavakom, A. Analyst 2015, 140, 1886. doi: 10.1039/C4AN01843E
140. [140]
  Chakravarty, S.; Gogoi, B.; Sen Sarma, N. J. Lumin. 2015, 165, 6. doi: 10.1016/j.jlumin.2015.04.006
141. [141]
  Gogoi, B.; Sen Sarma, N. ACS Appl. Mater. Interfaces 2015, 7, 11195. doi: 10.1021/acsami.5b01102
142. [142]
  Kabessa, Y.; Eyal, O.; Bar-On, O.; Korouma, V.; Yagur-Kroll, S.; Belkin, S.; Agranat, A. J. Biosens. Bioelectron. 2016, 79, 784. doi: 10.1016/j.bios.2016.01.011
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