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
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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]
(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) Kim, K.; Tsay, O. G.; Atwood, D. A.; Churchill, D. G. Chem. Rev. 2011, 111, 5345. doi: 10.1021/cr100193y
-
[3]
(3) Zhou, X.; Lee, S. Y.; Xu, Z. C.; Yoon, J. Chem. Rev. 2015, 115, 7944. doi: 10.1021/cr500567r
-
[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) 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) Carniato, F.; Bisio, C.; Psaro, R.; Marchese, L.; Guidotti, M. Angew. Chem. Int. Edit. 2014, 53, 10095. doi: 10.1002/anie.201405134
-
[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) 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) 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) Sarkar, S.; Shunmugam, R. Chem. Commun. 2014, 50, 8511. doi: 10.1039/C4CC03361B
-
[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) 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) Wallace, K. J.; Morey, J.; Lynch, V. M.; Anslyn, E. V. New J. Chem. 2005, 29, 1469. doi: 10.1039/B506100H
-
[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) Rusu, A. D.; Moleavin, I. A.; Hurduc, N.; Hamel, M.; Rocha, L. Chem. Commun. 2014, 50, 9965. doi: 10.1039/c4cc03580a
-
[16]
(16) Brown, K. Science 2004, 305, 1228. doi: 10.1126/science.305.5688.1228
-
[17]
(17) Eubanks, L. M.; Dickerson, T. J.; Janda, K. D. Chem. Soc. Rev. 2007, 36, 458. doi: 10.1039/B615227A
-
[18]
(18) Yang, Y. M.; Ji, H. F.; Thundat, T. J. Am. Chem. Soc. 2003, 125, 1124. doi: 10.1021/ja028181n
-
[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) Gurton, K. P.; Felton, M.; Tober, R. Opt. Lett. 2012, 37, 3474. doi: 10.1364/OL.37.003474
-
[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) Lin, Y. H.; Lu, F.; Wang, J. Electroanalysis 2004, 16, 145. doi: 10.1002/elan.200302933
-
[23]
(23) Zhou, Y. X.; Yu, B.; Shiu, E.; Levon, K. Anal. Chem. 2004, 76, 2689. doi: 10.1021/ac035072y
-
[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) 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) 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) 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) 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) 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) Xuan, W. M.; Cao, Y. T.; Zhou, J. H.; Wang, W. Chem. Commun. 2013, 49, 10474. doi: 10.1039/C3CC46095A
-
[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) Zhang, S. W.; Swager, T. M. J. Am. Chem. Soc. 2003, 125, 3420. doi: 10.1021/ja029265z
-
[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) 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) 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) Lei, Z. H.; Yang, Y. J. J. Am. Chem. Soc. 2014, 136, 6594. doi: 10.1021/ja502945q
-
[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) 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) Bencic-Nagale, S.; Sternfeld, T.; Walt, D. R. J. Am. Chem. Soc. 2006, 128, 5041. doi: 10.1021/ja057057b
-
[40]
(40) Dale, T. J.; Rebek, J., Jr. J. Am. Chem. Soc. 2006, 128, 4500. doi: 10.1021/ja057449i
-
[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) Dale, T. J.; Rebek, J., Jr. Angew. Chem. Int. Edit. 2009, 48, 7850. doi: 10.1002/anie.200902820
-
[43]
(43) Wu, X. J.; Wu, Z. S.; Han, S. F. Chem. Commun. 2011, 47, 11468. doi: 10.1039/C1CC15250E
-
[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) 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) Tolosa, J.; Zucchero, A. J.; Bunz, U. H. F. J. Am. Chem. Soc. 2008, 130, 6498. doi: 10.1021/ja800232f
-
[47]
(47) Klok, H. A.; Hwang, J. J.; Iyer, S. N.; Stupp, S. I. Macromolecules 2002, 35, 746. doi: 10.1021/ma010907x
-
[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) 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) Pangeni, D.; Nesterov, E. E. Macromolecules 2013, 46, 7266. doi: 10.1021/ma4016278
-
[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) Marx, V. Nat. Methods 2015, 12, 187. doi: 10.1038/nmeth.3295
-
[53]
(53) Dennison, G. H.; Johnston, M. R. Chem. -Eur. J. 2015, 21, 6328. doi: 10.1002/chem.201406213
-
[54]
(54) Goswami, S. Das, S.; Aich, K. RSC Adv. 2015, 5, 28996. doi: 10.1039/C5RA01216C
-
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