Citation: QI Yan-Yu, SUN Xiao-Huan, CHANG Xing-Mao, KANG Rui, LIU Kai-Qiang, FANG Yu. A New Type of 1,4-Bis(phenylethynyl)benzene Derivatives: Optical Behavior and Sensing Applications[J]. Acta Physico-Chimica Sinica, ;2016, 32(1): 373-379. doi: 10.3866/PKU.WHXB201511091 shu

A New Type of 1,4-Bis(phenylethynyl)benzene Derivatives: Optical Behavior and Sensing Applications

1.
Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, P. R. China

Corresponding author: FANG Yu,
Received Date: 11 October 2015
Available Online: 9 November 2015
Fund Project: 国家自然科学基金(21273141,21527802) (21273141,21527802)“111”计划(B14041) (B14041)长江学者与创新团队发展计划(IRT1070)资助项目 (IRT1070)

A new and optically stable fluorescent derivative (OPBMQ) of 1,4-bis(phenylethynyl)benzene (BPEB) with 8-hydroxyquinoline (8-HQ) as a capturing unit and cholesterol (Chol) as an auxiliary structure was designed and synthesized. Fluorescence studies demonstrated that the fluorescence emission of the compound in the aqueous phase is characterized by two distinct and independent emissions, of which one originates from 8-HQ and the other from BPEB. Importantly, the emission is highly selective and sensitive to the presence of diethyl chlorophosphate (DCP), a simulant of Sarin. The calculated detection limit (DL) is lower than 1 × 10^-9 mol·L^-1. Moreover, no significant response was observed when the probe was exposed to simulants of other nerve agents, relevant organophosphorus pesticides, or even their mixtures. More importantly, regardless of whether Milli-Q water, tap water or even sea water was employed as solvent, the presence of the mixture of the interferents studied did not show any significant effect on the detection of DCP. In particular, the sensitive and highly selective detection of DCP was also realized by naked-eye observation, providing a simple and low-cost protocol for the on-site and real-time detection of the chemical. Based on this discovery, a DCP monitoring device was successfully developed.
- 1,4-Bis(phenylethynyl)benzene,
- Fluorescence,
- Sarin,
- 8-Hydroxyquinoline,
- Diethyl chlorophosphate
1. [1]
  (1) Kim, H. J.; Lee, J. H.; Lee, H.; Lee, J. H.; Lee, J. H.; Jung, J. H.; Kim, J. S. Adv. Funct. Mater. 2011, 21, 4035. doi: 10.1002/adfm.v21.21
2. [2]
  (2) Kim, K.; Tsay, O. G.; Atwood, D. A.; Churchill, D. G. Chem. Rev. 2011, 111, 5345. doi: 10.1021/cr100193y
3. [3]
  (3) Zhou, X.; Lee, S. Y.; Xu, Z. C.; Yoon, J. Chem. Rev. 2015, 115, 7944. doi: 10.1021/cr500567r
4. [4]
  (4) Okumura, T.; Ariyoshi, K.; Hitomi, T.; Hirahara, K.; Itoh, T.; Iwamura, T.; Nakashima, A.; Motomura, Y.; Taki, K.; Suzuki, K. Toxin Rev. 2009, 28, 255. doi: 10.3109/15569540903338040
5. [5]
  (5) Chao, L. L.; Rothlind, J. C.; Cardenasa, V. A.; Meyerhoff, D. J.; Weiner, M. W. Neurotoxicology 2010, 31, 493. doi: 10.1016/j.neuro.2010.05.006
6. [6]
  (6) Carniato, F.; Bisio, C.; Psaro, R.; Marchese, L.; Guidotti, M. Angew. Chem. Int. Edit. 2014, 53, 10095. doi: 10.1002/anie.201405134
7. [7]
  (7) Mahapatra, A. K.; Maiti, K.; S. Manna, K.; Maji, R.; Mondal, S.; Mukhopadhyay, C. D.; Sahooc, P.; Mandald, D. Chem. Commun. 2015, 51, 9729. doi: 10.1039/C5CC02991K
8. [8]
  (8) Jo, S.; Kim, J.; Noh, J.; Kim, D.; Jang, G.; Lee, N.; Lee, E.; Lee, T. S. ACS Appl. Mater. Interfaces 2014, 6, 22884. doi: 10.1021/am507206x
9. [9]
  (9) Bai, H. H.; Guo, L.; Feng, J. L.; Feng, C. L.; Chen, J.; Xie, J. W. Chin. J. Anal. Chem. 2008, 36, 1269. [白海红, 郭磊, 冯建林, 冯翠玲, 陈佳, 谢剑炜. 分析化学, 2008, 36, 1269.] doi: 10.1016/S1872-2040(08)60069-9
10. [10]
  (10) Sarkar, S.; Shunmugam, R. Chem. Commun. 2014, 50, 8511. doi: 10.1039/C4CC03361B
11. [11]
  (11) Wu, W. H.; Dong, J. J.; Wang, X.; Li, J.; Sui, S. H.; Chen, G. Y.; Liu, J. W.; Zhang, M. Analyst 2012, 137, 3224. doi: 10.1039/C2AN35428D
12. [12]
  (12) Ramaseshan, R.; Sundarrajan, S.; Liu, Y. J.; Barhate, R. S.; Lala, N. L.; Ramakrishna, S. Nanotechnology 2006, 17, 2947. doi: 10.1088/0957-4484/17/12/021
13. [13]
  (13) Wallace, K. J.; Morey, J.; Lynch, V. M.; Anslyn, E. V. New J. Chem. 2005, 29, 1469. doi: 10.1039/B506100H
14. [14]
  (14) Cojocaru, B.; Neaţu, Ş.; Pârvulescu, V. I.; Şomoghi, V.; Petrea, N.; Epure, G.; Alvaro, M.; Garcia, H. ChemSusChem 2009, 2, 427. doi: 10.1002/cssc.200800246
15. [15]
  (15) Rusu, A. D.; Moleavin, I. A.; Hurduc, N.; Hamel, M.; Rocha, L. Chem. Commun. 2014, 50, 9965. doi: 10.1039/c4cc03580a
16. [16]
  (16) Brown, K. Science 2004, 305, 1228. doi: 10.1126/science.305.5688.1228
17. [17]
  (17) Eubanks, L. M.; Dickerson, T. J.; Janda, K. D. Chem. Soc. Rev. 2007, 36, 458. doi: 10.1039/B615227A
18. [18]
  (18) Yang, Y. M.; Ji, H. F.; Thundat, T. J. Am. Chem. Soc. 2003, 125, 1124. doi: 10.1021/ja028181n
19. [19]
  (19) Thompson, C. H.; Hu, J.; Kaganove, S. N.; Keinath, S. E.; Keeley, D. L.; Dvornic, P. R. Chem. Mater. 2004, 16, 5357. doi: 10.1021/cm040346z
20. [20]
  (20) Gurton, K. P.; Felton, M.; Tober, R. Opt. Lett. 2012, 37, 3474. doi: 10.1364/OL.37.003474
21. [21]
  (21) Steiner, W. E.; Klopsch, S. J.; English, W. A.; Clowers, B. H.; Hill, H. H. Anal. Chem. 2005, 77, 4792. doi: 10.1021/ac050278f
22. [22]
  (22) Lin, Y. H.; Lu, F.; Wang, J. Electroanalysis 2004, 16, 145. doi: 10.1002/elan.200302933
23. [23]
  (23) Zhou, Y. X.; Yu, B.; Shiu, E.; Levon, K. Anal. Chem. 2004, 76, 2689. doi: 10.1021/ac035072y
24. [24]
  (24) Hammonda, M. H.; Johnson, K. J.; Rose-Pehrsson, S. L.; Ziegler, J.; Walker, H.; Caudy, K.; Gary, D.; Tillett, D. Sens. Actuators B 2006, 116, 135.
25. [25]
  (25) Cao, X. H.; Mello, S. V.; Leblanc, R. M.; Rastogi, V. K.; Cheng, T. C.; DeFrank, J. J. J. Colloids Surf. A 2004, 250, 349. doi: 10.1016/j.colsurfa.2004.01.043
26. [26]
  (26) Orbulescu, J.; Constantine, C. A.; Rastogi, V. K.; Shah, S. S.; DeFrank, J. J.; Leblanc, R. M. Anal. Chem. 2006, 78, 7016. doi: 10.1021/ac061118m
27. [27]
  (27) Viveros, L.; Paliwal, S.; McCrae, D.; Wild, J.; Simonian, A. Sens. Actuators B 2006, 115, 150. doi: 10.1016/j.snb.2005.08.032
28. [28]
  (28) Asbury, G. R.; Wu, C.; Siems, W. F.; Hill, H. H., Jr. Anal. Chim. Acta 2000, 404, 273. doi: 10.1016/S0003-2670(99)00726-6
29. [29]
  (29) Zhang, Z.; Fan, J.; Yu, J. M.; Zheng, S. R.; Chen, W. J.; Li, H. G.; Wang, Z. J.; Zhang, W. G. ACS Appl. Mater. Interfaces 2012, 4, 944. doi: 10.1021/am201603n
30. [30]
  (30) Xuan, W. M.; Cao, Y. T.; Zhou, J. H.; Wang, W. Chem. Commun. 2013, 49, 10474. doi: 10.1039/C3CC46095A
31. [31]
  (31) Kwon, O. S.; Park, S. J.; Lee, J. S.; Park, E.; Kim, T.; Park, H. W.; You, S. A.; Yoon, H.; Jang, J. Nano Lett. 2012, 12, 2797. doi: 10.1021/nl204587t
32. [32]
  (32) Zhang, S. W.; Swager, T. M. J. Am. Chem. Soc. 2003, 125, 3420. doi: 10.1021/ja029265z
33. [33]
  (33) Louise-Leriche, L.; Pǎunescu, E.; Saint-André, G.; Baati, R.; Romieu, A.; Wagner, A.; Renard, P. Y. Chem. Eur. J. 2010, 16, 3510. doi: 10.1002/chem.200902986
34. [34]
  (34) Singh, V. V.; Kaufmann, K.; Orozco, J.; Li, J. X.; Galarnyk, M.; Arya, G.; Wang, J. Chem. Commun. 2015, 51, 11190. doi: 10.1039/C5CC04120A
35. [35]
  (35) Zhao, L.; Yan, Y.; Huang, J. B. Acta Phys. -Chim. Sin. 2010, 26, 840. [赵莉, 阎云, 黄建滨. 物理化学学报, 2010, 26, 840.] doi: 10.3866/PKU.WHXB20100429
36. [36]
  (36) Lei, Z. H.; Yang, Y. J. J. Am. Chem. Soc. 2014, 136, 6594. doi: 10.1021/ja502945q
37. [37]
  (37) Jo, S.; Kim, D.; Son, S. H.; Kim, Y.; Lee, T. S. ACS Appl. Mater. Interfaces 2014, 6, 1330. doi: 10.1021/am405430t
38. [38]
  (38) Wu, Z. S.; Wu, X. J.; Yang, Y. H.; Wen, T. B.; Han, S. F. Bioorg. Med. Chem. Lett. 2012, 22, 6358. doi: 10.1016/j.bmcl.2012.08.077
39. [39]
  (39) Bencic-Nagale, S.; Sternfeld, T.; Walt, D. R. J. Am. Chem. Soc. 2006, 128, 5041. doi: 10.1021/ja057057b
40. [40]
  (40) Dale, T. J.; Rebek, J., Jr. J. Am. Chem. Soc. 2006, 128, 4500. doi: 10.1021/ja057449i
41. [41]
  (41) Jang, Y. J.; Tsay, O. G.; Murale, D. P.; Jeong, J. A.; Segev, A.; Churchill, D. G. Chem. Commun. 2014, 50, 7531. doi: 10.1039/C4CC02689F
42. [42]
  (42) Dale, T. J.; Rebek, J., Jr. Angew. Chem. Int. Edit. 2009, 48, 7850. doi: 10.1002/anie.200902820
43. [43]
  (43) Wu, X. J.; Wu, Z. S.; Han, S. F. Chem. Commun. 2011, 47, 11468. doi: 10.1039/C1CC15250E
44. [44]
  (44) He, L. P.; Liang, J. J.; Cong, Y.; Chen, X.; Bu, W. F. Chem. Commun. 2014, 50, 10841. doi: 10.1039/C4CC04243C
45. [45]
  (45) Kim, I. B.; Erdogan, B.; Wilson, J. N.; Bunz, U. H. F. Chem. -Eur. J. 2004, 10, 6247. doi: 10.1002/chem.200400788
46. [46]
  (46) Tolosa, J.; Zucchero, A. J.; Bunz, U. H. F. J. Am. Chem. Soc. 2008, 130, 6498. doi: 10.1021/ja800232f
47. [47]
  (47) Klok, H. A.; Hwang, J. J.; Iyer, S. N.; Stupp, S. I. Macromolecules 2002, 35, 746. doi: 10.1021/ma010907x
48. [48]
  (48) Xue, M.; Miao, Q.; Fang, Y. Acta Phys. -Chim. Sin. 2013, 29, 2005. [薛敏, 苗青, 房喻. 物理化学学报, 2013, 29, 2005.] doi: 10.3866/PKU.WHXB201306142
49. [49]
  (49) Zhang, L.; You, C. J.; Chen, J. P.; Yang, G. Q.; Li, Y. Acta Phys. -Chim. Sin. 2006, 22, 326. [张鲁, 游长江, 陈金平, 杨国强, 李嫕. 物理化学学报, 2006, 22, 326.] doi: 10.1016/S1872-1508(06)60008-9
50. [50]
  (50) Pangeni, D.; Nesterov, E. E. Macromolecules 2013, 46, 7266. doi: 10.1021/ma4016278
51. [51]
  (51) Chang, X. M.; Wang, G.; Yu, C. M.; Wang, Y. R.; He, M. X.; Fan J.; Fang, Y. J. Photochem. Photobiol. A 2015, 298, 9. doi: 10.1016/j.jphotochem.2014.10.008
52. [52]
  (52) Marx, V. Nat. Methods 2015, 12, 187. doi: 10.1038/nmeth.3295
53. [53]
  (53) Dennison, G. H.; Johnston, M. R. Chem. -Eur. J. 2015, 21, 6328. doi: 10.1002/chem.201406213
54. [54]
  (54) Goswami, S. Das, S.; Aich, K. RSC Adv. 2015, 5, 28996. doi: 10.1039/C5RA01216C
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