苯并咪唑基荧光化学传感器的合成与应用研究进展
收稿日期: 2015-07-20
修回日期: 2015-08-21
网络出版日期: 2015-08-31
基金资助
广东省自然科学基金(No. 2014A030313429)、广东省高等学校人才引进专项资金(No. 粤财教[2011]431号)、国家自然科学基金(No. 31200439)资助项目.
Progress in the Synthesis and Application of Benzimidazole-Based Fluorescent Chemosensors
Received date: 2015-07-20
Revised date: 2015-08-21
Online published: 2015-08-31
Supported by
Project supported by the Natural Science Foundation of Guangdong Province (No. 2014A030313429), the 3rd Talents Special Funds of Guangdong Higher Education (No. Guangdong-Finance-Education [2011]431) and the National Natural Science Foundation of China (No. 31200439).
吴彦城 , 尤嘉宜 , 关丽涛 , 石杰 , 曹梁 , 汪朝阳 . 苯并咪唑基荧光化学传感器的合成与应用研究进展[J]. 有机化学, 2015 , 35(12) : 2465 -2486 . DOI: 10.6023/cjoc201507022
Many benzimidazole compounds can emit characteristic fluorescence in various organic solvents and aqueous solutions, and their fluorescence properties can be influenced by some factors under certain conditions, which make them used in the field of fluorescence detection. Recently, more and more attention has been attached to the benzimidazole-based fluorescent chemosensors. Their synthesis and the extensive application in the detection of metal ions, anions, inorganic small molecules, metal oxide nanoparticles, organic small molecules, and so on are reviewed. The development trend of benzimidazole-based fluorescent chemosensors is prospected.
Key words: benzimidazole; sensor; synthesis; fluorescence detection; progress
[1] Singh, S.; Bharti, N.; Mohapatra, P. P. Chem. Rev. 2009, 109, 1900.
[2] Marson, C. M. Chem. Rev. 2011, 111, 7121.
[3] Mao, Z.-Z.; Wang, Z.-Y.; Hou, X.-N.; Song, X.-M.; Luo, Y.-F. Chin. J. Org. Chem. 2008, 28, 542 (in Chinese). (毛郑州, 汪朝阳, 侯晓娜, 宋秀美, 罗玉芬, 有机化学, 2008, 28, 542.)
[4] Zhu, G.-M.; Yang, L.-Y.; Cui, D.-M. Chin. J. Org. Chem. 2014, 34, 495 (in Chinese.) (朱观明, 杨柳阳, 崔冬梅. 有机化学, 2014, 34, 495.)
[5] Peng, P.; Xiong, J.-F.; Li, B.; Mo, G.-Z.; Chen, R.-H.; Wang, Z.-Y. Chin. J. Org. Chem. 2013, 33, 1891 (in Chinese). (彭湃, 熊金锋, 李豹, 莫广珍, 陈任宏, 汪朝阳, 有机化学, 2013, 33, 1891.)
[6] Li, Y.; Ma, H.-Q.; Wang, Y.-L. Chin. J. Org. Chem. 2008, 28, 210 (in Chinese). (李焱, 马会强, 王玉炉, 有机化学, 2008, 28, 210.)
[7] Mao, Z.-Z.; Li, J.-X.; Xue, F.-L.; Chen, R.-H.; Wang, Z.-Y. Chem. Res. Appl. 2012, 24, 497 (in Chinese). (毛郑州, 李建晓, 薛福玲, 陈任宏, 汪朝阳, 化学研究与应用, 2012, 24, 497.)
[8] Xiong, J.-F.; Luo, S.-H.; Wang, Q.-F.; Wang, Z.-Y.; Qi, J. Des. Monomers Polym. 2013, 16, 389.
[9] Xiong, J.-F.; Wang,Q.-F.; Peng, P.; Shi, J.; Wang, Z.-Y.; Yang, C.-L. J. Appl. Polym. Sci. 2014, 131, 40275.
[10] Xiong, J.-F.; Luo, S.-H.; Huo, J.-P.; Liu, J.-Y.; Chen, S.-X.; Wang, Z.-Y. J. Org. Chem. 2014, 79, 8366.
[11] Tzeng, B. C.; Chen, B. S.; Chen, C. K.; Chang, Y. P.; Tzeng, W. C.; Lin, T. Y.; Lee, G. H.; Chou, P. T.; Fu, Y. J.; Chang, A. H. H. Inorg. Chem. 2011, 50, 5379.
[12] Yu, H.; Wang, S.; Son, Y. A. Mol. Cryst. Liq. Cryst. 2012, 568, 117.
[13] Zhong, K.-L.; Zhou, X.; Hou, R.-B.; Zhou, P.; Hou, S.-H.; Bian, Y.-J.; Zhang, G.; Tang, L.-J.; Shang, X.-H. RSC Adv. 2014, 4, 16612.
[14] Hu, J.-H.; Li, J.-B.; Qi, J.; Chen, J.-J. New J. Chem. 2015, 39, 843.
[15] Yang, Y.; Li, B.; Zhang, L.-M.; Guan, Y.-L. J. Lumin. 2014, 145, 895.
[16] Peng, P.; Xiong, J.-F.; Mo, G.-Z.; Zheng, J.-L.; Chen, R.-H.; Chen, X.-Y.; Wang, Z.-Y. Amino Acids 2014, 46, 2427.
[17] Chen, R.-H.; Xiong, J.-F.; Peng, P.; Mo, G.-Z.; Tang, X.-S.; Wang, Z.-Y.; Wang X.-F. Asian J. Chem. 2014, 26, 926.
[18] Ghosh, K.; Sarkar, T. Supramol. Chem. 2012, 24, 748.
[19] Madhu, S.; Sharma, D. K.; Basu, S. K.; Jadhav, S.; Chowdhury, A.; Ravikanth, M. Inorg. Chem. 2013, 52, 11136.
[20] Wang, Q.-M.; Tan, C.-L. Anal. Chim. Acta 2011, 708, 111.
[21] Kim, S. J.; Kool, E. T. J. Am. Chem. Soc. 2006, 128, 6164.
[22] Jayabharathi, J.; Thanikachalam, V.; Jayamoorthy, K.; Sathishkumar, R. Spectrochim. Acta, Part A 2012, 97, 384.
[23] Cimen, O. Z; Dincalp, H.; Varlikli, C. Sens. Actuators B 2015, 209, 853.
[24] Li, J.-B.; Hu, Q.-H.; Yu, X.-L.; Zeng, Y.; Cao, C.-C.; Liu, X.-W.; Guo, J.; Pan, Z.-Q. J. Fluoresc. 2011, 21, 2005.
[25] Zhang, Y.; Wang, J.-M.; Shu, W.-H.; Chen, Q.; Ma, Z.-G.; Chen, X.-M. Chin. J. Inorg. Chem. 2013, 29, 150 (in Chinese). (张勇, 王继猛, 舒威虎, 陈其, 马志刚, 陈雪梅. 无机化学学报, 2013, 29, 150.)
[26] Liu, J.; Lin, Q.; Zhang, Y.-M.; Wei, T.-B. Sci. China Chem. 2014, 57, 1257.
[27] Wang, M.; Wang, J.-G.; Xue, W.-J.; Wu, A.-X. Dyes Pigm. 2013, 97, 475.
[28] Jung, H. J.; Singh, N.; Jang, D. O. Tetrahedron Lett. 2008, 49, 2960.
[29] Lee, D. Y.; Singh, N.; Jang, D. O. Tetrahedron Lett. 2010, 51, 1103.
[30] Lu, L.-J.; Yin, M.-C.; Fan, Y-T.; Hou, H.-W.; Wu, Y.-J. Chin. J. Inorg. Chem. 2001, 17, 478 (in Chinese). (卢会杰, 尹明彩, 樊耀亭, 侯红卫, 吴养洁, 无机化学学报, 2001, 17, 478.)
[31] Lee, D. Y.; Singh, N.; Jang, D. O. Tetrahedron Lett. 2011, 52, 1368.
[32] Lee, D. Y.; Singh, N.; Jang, D. O. Tetrahedron Lett. 2011, 52, 3886.
[33] Tang, L. J.; Zhou, P.; Zhong, K. L.; Hou, S. H. Sens. Actuators, B 2013, 182, 439.
[34] Tang, L. J.; Wang, N. N.; Zhang, Q.; Guo, J. J.; Nandhakumar, R. Tetrahedron Lett. 2013, 54, 536.
[35] Saluja, P.; Kaur, N.; Singh, N.; Jang, D. O. Tetrahedron Lett. 2012, 53, 3292.
[36] Tang, L.-J.; Cai, M.-J. Sens. Actuators B 2012, 173, 862.
[37] Wang, X.-J.; Xu, T.; Duan, H.-D. Sens. Actuators B 2015, 214, 138.
[38] Tang, L.-J.; Dai, X.; Cai, M.-J.; Zhao, J.; Zhou, P.; Huang, Z.-L. Spectrochim. Acta, Part A 2014, 122, 656.
[39] Mahiya, K.; Mathur, P. J. Fluoresc. 2013, 23, 767.
[40] Mahiya, K.; Mathur, P. Spectrochim. Acta, Part A 2013, 113, 386.
[41] Ghosh, K.; Sarkar, T. Supramol. Chem. 2011, 23, 435.
[42] Tang, L.-J.; Li, F.-F.; Liu, M.-H.; Nandhakumar, R. Bull. Korean Chem. Soc. 2010, 31, 3212.
[43] Chipem, F. A. S.; Behera, S. K.; Krishnamoorthy, G. Sens. Actuators B 2014, 191, 727.
[44] Pandey, A. D.; Pissurlenkar, R. R. S.; Karnik, A. V. J. Inclusion Phenom. Macrocycl. Chem. 2015, 81,251.
[45] Pathak, R. K.; Hinge, V. K.; Mondal, P.; Rao, C. P. Dalton Trans. 2012, 41, 10652.
[46] Goswami, S.; Maity, S.; Maity, A. C.; Maity, A. K.; Das, A. K.; Saha, P. RSC Adv. 2014, 4, 6300.
[47] Lal, A. K.; Milton, M. D. Sens. Actuators B 2014, 202, 257.
[48] Jayabharathi, J.; Thanikachalam, V.; Jayamoorthy, K. Spectrochim. Acta, Part A 2012, 95, 143.
[49] El Majzoub, A.; Cadiou, C.; Dechamps-Olivier, I.; Chuburu, F.; Aplincourt, M. Eur. J. Inorg. Chem. 2007, 5087.
[50] El Majzoub, A.; Cadiou, C.; Dechamps-Olivier, I.; Chuburu, F.; Aplincourt, M.; Tinant, B. Inorg. Chim. Acta 2009, 362, 1169.
[51] El Majzoub, A.; Cadiou, C.; Dechamps-Olivier, I.; Tinant, B.; Chuburu, F. Inorg. Chem. 2011, 50, 4029.
[52] Zhong, K.-L.; Cai, M.-J.; Hou, S.-H.; Bian, Y.-J.; Tang, L.-J. Bull. Korean Chem. Soc. 2014, 35, 489.
[53] Tang, L.-J.; Cai, M.-J.; Zhou, P.; Zhao, J.; Zhong, K.-L.; Hou, S.-H.; Bian, Y.-J. RSC Adv. 2013, 3, 16802.
[54] Tang, L.-J.; Cai, M.-J.; Zhou, P.; Zhao, J. ; Huang, Z.-L.; Zhong, K.-L.; Hou, S.-H.; Bian, Y.-J. J. Lumin. 2014, 147, 179.
[55] Martin, D.; Rouffet, M.; Cohen, S. M.. Inorg. Chem. 2010, 49, 10226.
[56] Henary, M. M.; Wu, Y.; Fahrni, C. J. Chem. Eur. J. 2004, 10, 3015.
[57] Henary, M. M.; Fahrni, C. J. J. Phys. Chem. A 2002, 106, 5210.
[58] Kim, M. J.; Kaur, K.; Singh, N.; Jang, D. O. Tetrahedron 2012, 68, 5429.
[59] Mashraqui, S. H.; Sundaram, S.; Khan, T. Chem. Lett. 2006, 135, 786.
[60] Lohar, S.; Karak, D.; Guha, S.; Banerjee, A.; Sahana, A.; Das, D. Spectrosc. Lett. 2013, 46, 28.
[61] Kumar, A.; Singh, A. K.; Gupta, T. Analyst 2013, 138, 3356.
[62] Velmurugan, K.; Raman, A;. Don, D.; Tang, L.-J.; Easwaramoorthi, S.; Nandhakuma, R. RSC Adv. 2015, 5, 44463.
[63] Cao, W.; Zheng, X.-J.; Sun, J.-P.; Wong, W.-T.; Fang, D.-C; Zhang, J.-X.; Jin, L.-P. Inorg. Chem. 2014, 53, 3012.
[64] Jeyanthi, D.; Iniya, M.; Krishnaveni, K.; Chellappa, D. RSC Adv. 2013, 3, 20984.
[65] Iniya, M.; Jeyanthi, D.; Krishnaveni, K.; Chellappa, D. J. Lumin. 2014, 157, 383.
[66] Ma, T.; Zhang, J.; Liu, L.-Z. He, Y.; Zhang, Z.-T. Chin. J. Org. Chem. 2014, 34, 1780 (in Chinese). (马拓, 张瑾, 刘龙珠, 贺云, 张尊听, 有机化学, 2014, 34, 1780.)
[67] Alvaro, M.; Garcia, H.; Palomares, E.; Achour, R.; Moussaif, A.; Zniber, R. Chem. Phys. Lett. 2001, 350, 240.
[68] Saluja, P.; Sharma, H.; Kaur, N.; Singh, N.; Jang, D. O. Tetrahedron 2012, 68, 2289.
[69] Saluja, P.; Kaur, N.; Singh, N.; Jang, D. O. Tetrahedron 2012, 68, 8551.
[70] Alizadeh, A.; Khodaei, M. M.; Hamidi, Z. Sens. Actuators, B 2014, 190, 782.
[71] Firooz, A. R.; Ensafi, A. A.; Kazemifard, N.; Sharghi, H. Talanta 2012, 101, 171.
[72] Dessingou, J.; Mitra, A.; Tabbasum, K.; Baghel, G. S.; Rao, C. P. J. Org. Chem. 2012, 77, 371.
[73] Li, G.; Gong, W.-T.; Ye, J.-W.; Lin, Y.-A.; Ning, G.-L. Tetrahedron Lett. 2011, 52, 1313.
[74] Pang, S.-T.; Zheng, Y.-H.; Zhou, Z.; Tan, C.-L.; Wang, Q.-M.; Li, X.-D. Opt. Mater. 2013, 35, 1157.
[75] Wang, J.-A.; Bai, F.-Q.; Xia, B.-H.; Sun, L.; Zhang, H.-X. J. Phys. Chem. A 2011, 115, 1985.
[76] Khanmohammadi, H.; Rezaeian, K. New J. Chem. 2014, 38, 5536.
[77] Chetia, B.; Iyer, P. K. Sens. Actuators, B 2014, 201, 191.
[78] Gupta, A. S.; Paul, K.; Luxami, V. Spectrochim. Acta, Part A 2015, 138, 67.
[79] Madhu, S.; Ravikanth, M. Inorg. Chem. 2014, 53, 1646.
[80] Bren, V. A.; Tolpygin, I. E.; Tikhomirova, K. S.; Popova, O. S.; Bren, Z. V.; Revinskii, Y. V.; Dubonosov, A. D.; Minkin, V. I. Chem. Heterocycl. Compd. 2014, 50, 1665.
[81] Moon, K. S.; Singh, N.; Lee, G. W.; Jang, D. O. Tetrahedron 2007, 63, 9106.
[82] Shao, J.; Qiao, Y.-H.; Lin, H.; Lin, H.-K. J. Fluoresc. 2009, 19, 183.
[83] Yang, X.-F.; Qi, H.-P.; Wang, L.-P.; Su, Z.; Wang, G. Talanta 2009, 80, 92.
[84] Kaur, N.; Dhaka, G.; Singh, J. Tetrahedron Lett. 2015, 56, 1162.
[85] Sharma, H.; Guadalupe, H. J.; Narayanan, J.; Hofeld, H.; Pandiyan, T. Singh, N. Anal. Methods 2013, 5, 3880.
[86] Sharma, H.; Bhardwaj, V. K.; Kaur, N.; Singh, N.; Jang, D. O. Tetrahedron Lett. 2013, 54, 5967.
[87] Lee, D. Y.; Singh, N.; Kim, M. J.; Jang, D. O. Org. Lett. 2011, 13, 3024.
[88] Mahapatra, A. K.; Maiti, K.; Manna, S. K.; Maji, R.; Das M. C.; Pakhira, B.; Sarkar, S. Chem. Asian J. 2014, 9, 3623.
[89] Zelder, F. H. Inorg. Chem. 2008, 47, 1264.
[90] Li, J.-B.; Hu, J.-H.; Chen, J.-J.; Qi, J. Spectrochim. Acta, Part A 2014, 133, 773.
[91] Guo, Y.-Y.; Tang, X.-L.; Hou, F.-P.; Wu, J.; Dou, W.; Qin, W.-W.; Ru, J.-X.; Zhang, G.-L.; Liu, W.-S.; Yao, X.-J. Sens. Actuators B 2013, 181, 202.
[92] Chetia, B.; Iyer, P. K. Spectrochim. Acta, Part A 2011, 81, 313.
[93] Mukherjee, M.; Pal, S.; Sen, B.; Lohar, S.; Banerjee, S.; Banerjee, S.; Chattopadhyay, P. RSC Adv. 2014, 4, 27665.
[94] Wang, G.; Qi, H.-P.; Yang, X.-F. Luminescence 2013, 28, 97.
[95] Das, S.; Banerjee, A.; Lohar, S.; Sarkar, B.; Mukhopadhyay, S. K.; Matalobos, J. S.; Sahana, A.; Das, D. New J. Chem. 2014, 38, 2744.
[96] Kar, C.; Das, G. J. Photochem. Photobiol., A 2013, 251, 128.
[97] Sun, M.-T.; Yu, H.; Li, H.-H.; Xu, H.-D.; Huang, D.-J.; Wang, S.-H. Inorg. Chem. 2015, 54, 3766.
[98] Choi, H. W.; Kim, Y. S.; Yang, N. C.; Suh, D. H. J. Appl. Polym. Sci. 2004, 91, 90.
[99] Saikia, G.; Iyer, P. K. Macromolecules 2011, 44, 3753.
[100] Lirag, R. C.; Le, H. T. M.; Miljanic, O. S. Chem. Commun. 2013, 49, 4304.
[101] Zhao, Y; Gao, F.-B; Wu, K; Shen, C; Hong, H; Wang, X.-Y; Chen, J.-N; Mang, J.-F. Chin. J. Inorg. Chem. 2009, 25, 1513 (in Chinese). (赵勇, 高凤博, 吴可, 沈超, 洪浩, 王晓勇, 洪浩, 陈江宁, 张峻峰, 无机化学学报, 2009, 25, 1513.)
[102] Ishida, M.; Kim, P.; Choi, J.; Yoon, J.; Kim, D.; Sessler, J. L. Chem. Commun. 2013, 49, 6950.
[103] Karunakaran, C.; Jayabharathi, J.; Jayamoorthy, K.; Vinayagamoorthy, P. J. Photochem. Photobiol., A 2012, 247, 16.
[104] Karunakaran, C.; Jayabharathi, J.; Jayamoorthy, K. Sens. Actuators B 2013, 188, 207.
[105] Karunakaran, C.; Jayabharathi, J.; Jayamoorthy, K. Sens. Actuators B 2013, 182, 514.
[106] Han, Y.; Cao, H.-T.; Sun, H.-Z.; Shan, G.-G.; Wu, Y.; Su, Z.-M.; Liao, Y. J. Mater. Chem. C 2015, 3, 2341.
[107] Kandpal, M.; Bandela, A. K.; Hinge, V. K.; Rao, V. R.; Rao, C. P. ACS Appl. Mater. Interfaces 2013, 5, 13448.
[108] Xiong, J.-F.; Luo, S.-H.; Huo, J.-P.; Liu, J.-Y.; Chen, S.-X.; Wang, Z.-Y. J. Org. Chem. 2014, 79, 11619.
[109] Arici, M.; Yesilel, O. Z.; Tas, M. Dalton Trans. 2015, 44, 1627.
[110] Ghosh, K.; Sen, T.; Patra, A. New J. Chem. 2010, 34, 1387.
[111] Saluja, P.; Kaur, N.; Kang, J.; Singh, N.; Jang, D. O. Tetrahedron 2013, 69, 9001.
[112] Dai, M.; Zhu, W.-P.; Xu, Y.-F.; Qian, X.-H.; Liu, Y.; Xiao, Y.; You, Y. J Fluoresc. 2008, 18, 591.
[113] Khattar, R.; Mathur, P. Inorg. Chem. Commun. 2013, 31, 37.
[114] Ghosh, K.; Tarafdar, D.; Samadder, A.; Khuda-Bukhsh, A. R. RSC Adv. 2014, 4, 58530.
[115] Saeed, M. A.; Le, H. T. M.; Miljanic, O. S. Acc. Chem. Res. 2014, 47, 2074.
[116] Tolpygin, I. E.; Revinskii, Y. V.; Starikov, A. G.; Dubonosov, A. D.; Bren, V. A.; Minkin, V. I. Chem. Heterocycl. Compd. 2013, 47, 1230.
[117] You, Q.-H.; Fan, L.; Chan, W.-H.; Lee, A. W. M.; Shuang, S.-M. RSC Adv. 2013, 3, 15762.
[118] Kim, H. J.; Heo, C. H.; Kim, H. M. J. Am. Chem. Soc. 2013, 135, 17969.
[119] Ashton T. D.; Jolliffe K. A.; Pfeffer F. M. Chem. Soc. Rev. 2015, 44, 4547.
[120] Vendrell, M.; Zhai, D. T.; Er, J. C.; Chang, Y. T. Chem. Rev. 2012, 112, 4391.
[121] Daly, B.; Ling, J.; de Silva, A. P. C Chem. Soc. Rev. 2015, 44, 4203.
[122] Guo, X.-X.; Gu, D.-W.; Wu, Z.-X.; Zhang, W.-B. Chem. Rev. 2015, 115, 1622.
/
〈 |
|
〉 |