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2019 , Vol. 39 >Issue 12: 3414 - 3437

DOI: https://doi.org/10.6023/cjoc201906015

综述与进展

以苝二酰亚胺为发色团的荧光探针的研究进展

  • 石岩 ,
  • 于有伟 ,
  • 薛林 ,
  • 王延风
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  • a 山西师范大学食品科学学院 临汾 041004;
    b 山东省医学科学院药物研究所 济南 250062

收稿日期: 2019-06-13

  修回日期: 2019-07-05

  网络出版日期: 2019-07-24

基金资助

国家自然科学基金（No.21305079）资助项目.

收起

Progress of Fluorescent Probes with Perylene Tetracarboxylic Diimide as Chromophore

  • Shi Yan ,
  • Yu Youwei ,
  • Xue Lin ,
  • Wang Yanfeng
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  • a Collge of Food Sciences, Shanxi Normal University, Linfen, Shanxi 041004;
    b Institute of Materia Medica Shandong Academy of Medical Sciences, Jinan 250062

Received date: 2019-06-13

  Revised date: 2019-07-05

  Online published: 2019-07-24

Supported by

Project supported by the National Natural Science Foundation of China (No. 21305079).

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摘要

近年来，分子荧光探针以其高灵敏度、高选择性、专一性及设计的简便性等优点受到广泛的关注.苝二酰亚胺类（perylenetetracarboxylic diimide，PDI）衍生物具有良好的光热和化学稳定性、较高的荧光量子产率、较大的斯托克斯位移以及易修饰性等优点，能够作为优良的荧光探针发色团.苝四酸酐结构本身具有强吸电子性，易被还原而不易被氧化，因此能够作为良好的电子受体.但其自身结构容易发生π-π堆积，导致水溶性较差，限制了其在生物领域里的大范围应用.通过研究人员的努力，在PDI结构中引入亲水性基团改善了其水溶性.根据被检测物种的种类对PDI类荧光探针进行分类，详细介绍了近年来以PDI为发色团的荧光探针在离子检测、气体检测、生物分子检测等方面的研究进展，并探讨探针的设计方法、荧光响应机制以及应用.最后提出进一步构建新型PDI类衍生物分子荧光探针面临的挑战和未来发展方向，并对应用前景进行了展望.

关键词： 苝二酰亚胺; 荧光探针; 离子检测; 气体检测; 生物分子检测

本文引用格式

石岩 , 于有伟 , 薛林 , 王延风 . 以苝二酰亚胺为发色团的荧光探针的研究进展[J]. 有机化学, 2019 , 39(12) : 3414 -3437 . DOI: 10.6023/cjoc201906015

Abstract

In recent years, molecular fluorescent probes have attracted extensive attention due to their high sensitivity, high selectivity, specificity and simplicity of design. Perylene tetracarboxylic diimide derivatives (PDIs) are well known for their excellent photothermal stability, chemical stability, high fluorescence quantum yield, large stokes shift and easy modification. Therefore, they can be used as excellent fluorophores. PDI itself has strong electron-withdrawing group and easily to be reduced but it is hard to be oxidized. However, due to their inherent structure, the poor water solubility and aggregatable ablility limited their applications in biological fields. The water solubility of PDI was improved by introducing hydrophilic groups into the structure. Therefore, the PDIs with the unique advantages will have potential application values in the field of fluorescence probe and has been developed rapidly for the past few years. The development of PDI as a chromophore in fluorescent probe for the detection of ion, gas, biomolecules, etc. is systematically summarized. Meanwhile, the design of the probes, fluorescence response mechanism and application of the probe are also discussed. Finally, a novel type of PDI fluorescent probe is proposed. The challenge of construction of the PDIs and future development are also reviewed.

Key words： perylene tetracarboxylic diimide; fluorescent probe; ion-detection; gas detection; biomolecules detection

参考文献

[1] Huang, C.; Barlow, S.; Marder, S. R. J. Org. Chem. 2011, 76, 2386.
[2] Jozeliunaite, A.; Striela, R.; Labanauskas, L.; Orentas, E. Synthesis 2017, 49, 5176.
[3] Pasaogullari, N.; Icil, H.; Demuth, M. Dyes Pigm. 2006, 69, 118.
[4] Gao, G.; Liang, N.; Geng, H.; Jiang, W.; Fu, H.; Feng, J.; Hou, J.; Feng, X.; Wang, Z. J. Am. Chem. Soc. 2017, 139, 15914.
[5] Wang, H.; Chen, L.; Xiao, Y. J. Mater. Chem. C 2017, 5, 12816.
[6] Liu, Y.; Cole, M. D.; Jiang, Y.; Kim, P. Y.; Nordlund, D.; Emrick, T.; Russell, T. P. Adv. Mater. 2018, 30, 1705976.
[7] Villafiorita-Monteleone, F.; Kozma, E.; Giovanella, U.; Catellani, M.; Paolino, M.; Collico, V.; Colombo, M.; Cappelli, A.; Botta, C. Dyes Pigm. 2018, 149, 331.
[8] Türkmen, G.; Erten-Ela, S.; Icli, S. Dyes Pigm. 2009, 83, 297.
[9] Wang, B.; Yu, C. Angew. Chem. 2010, 122, 1527.
[10] Wang, B.; Zhu, Q.; Liao, D.; Yu, C. J. Mater. Chem. 2011, 21, 4821.
[11] Wang, B.; Jiao, H.; Li, W.; Liao, D.; Wang, F.; Yu, C. Chem. Commun. 2011, 47, 10269.
[12] Würthner, F. Chem. Commun. 2004, 1564.
[13] Guo, X.; Zhang, D.; Zhu, D. Adv. Mater. 2004, 2, 125.
[14] Lin, J.; Zhu, C.; Liu, J.; Chen, B.; Zhang, Y.; Xue, J.; Liu, J. Chin. J. Chem. 2014, 32, 1116.
[15] Wang, H.; Wang, D.; Wang, Q.; Li, X.; Schalley, C. Org. Biomol. Chem. 2010, 8, 1017.
[16] Cheng, H.; Qian, Y. Dyes Pigm. 2015, 112, 317.
[17] He, X.; Liu, H.; Li, Y.; Wang, S.; Li, Y.; Wang, N.; Xiao, J.; Xu, X.; Zhu, D. Adv. Mater. 2005, 17, 2811.
[18] Feng, X.; An, Y.; Yao, Z.; Li, C.; Shi, G. ACS Appl. Mater. Interfaces 2012, 4, 614.
[19] Zhong, L.; Xing, F.; Bai, Y.; Zhao, Y.; Zhu, S. Spectrochim. Acta, Part A 2013, 115, 370.
[20] Wang, Y.; Zhang, L.; Zhang, G.; Wu, Y.; Wu, S.; Yu, J.; Wang, L. Tetrahedron Lett. 2014, 55, 3218.
[21] Fu, L.-N.; Qiao, Z. R.; Jin, X.; Li, L. R. Chem. Res. Appl. 2019, 31, 624(in Chinese). (付丽娜, 乔振蕊, 金鑫, 李林容, 化学研究与应用, 2019, 31, 624.)
[22] Che, Y.; Yang, X.; Zang, L. Chem. Commun. 2008, 1413.
[23] Ruan, Y.; Li, A.; Zhao, J.; Shen, J.; Jiang, Y. Chem. Commun. 2010, 46, 4938.
[24] Fang, H.; Shellaiah, M.; Sinhg, A.; Raju Ramakrishnam, M. V.; Wu, Y.; Lin, H. Sens. Actuators, B 2014, 194, 229.
[25] Liu, K.; Xu, Z.; Yin, M.; Yang, W.; He, B.; Wei, W.; Shen, J. J. Mater. Chem. B 2014, 2, 2093.
[26] Han, A.; Liu, X.; Prestwich, G. D.; Zang, L. Sens. Actuators, B 2014, 198, 274.
[27] Malkongu, S.; Erdemir, S. Dyes Pigm. 2015, 113, 763.
[28] Erdemir, S.; Kocyigit, O.; Karakurt, S. Sens. Actuators, B 2015, 220, 381.
[29] Li, J.; Wu, Y.; Song, F.; Wei, G.; Cheng, Y.; Zhu, C. J. Mater. Chem. 2012, 22, 478.
[30] Zhao, X.; Gong, L.; Wu, Y.; Zhang, X.; Xie, J. Talanta 2016, 149, 98.
[31] Zhou, R.; Li, B.; Wu, N.; Gao, G.; You, J.; Lan, J. Chem. Commun. 2011, 47, 6668.
[32] Wang, H.; Lang, Y.; Wang, H.; Lou, J.; Guo, H.; Li, X. Tetrahedron 2014, 70, 1997.
[33] Zhang, L.; Wang, Y.; Yu, J.; Zhang, G.; Cai, X.; Wu, Y.; Wang, L. Tetrahedron Lett. 2013, 54, 4019.
[34] Kumar, K.; Bhargava, G.; Kumar, S.; Singh, P. New J. Chem. 2018, 42, 1010.
[35] Singh, P.; Mittal, L. S.; Vanita, V.; Kumar, K.; Walia, A.; Bhargava, G.; Kumar, S. J. Mater. Chem. B 2016, 4, 3750.
[36] Malkondu, S. Tetrahedron 2014, 70, 5580.
[37] Liu, X.; Zhang, N.; Zhou, J.; Chang, T.; Fang, C.; Shangguan, D. Analyst 2013, 138, 901.
[38] You, S.; Cai, Q.; Müillen, K.; Yang, W.; Yin, M. Chem. Commun. 2014, 50, 823.
[39] Wan, S.; Zheng, Y.; Shen, J.; Yang, W.; Yin, M. ACS Appl. Mater. Interfaces 2014, 6, 19515.
[40] Shen, Y.; Ma, X.; Zhang, B.; Zhou, Z.; Sun, Q.; Jin, E.; Sui, M.; Tang, J.; Wang, J.; Fan, M. Chem.-Eur. J. 2011, 17, 5319.
[41] Wu, Y.; Zhang, X.; Li, J.; Zhang, C.; Liang, H.; Mao, G.; Zhou, L.; Tan, W.; Yu, R. Anal. Chem. 2014, 86, 10389.
[42] Ling, J.; Naren, G.; Kelly, J.; Moody, T. S.; Prasanna de Silva, A. J. Am. Chem. Soc. 2015, 137, 3763.
[43] Huang, L.; Chang, T. S.-W. Chem. Commun. 2011, 47, 2291.
[44] Aigner, D.; Borisov, S. M.; Petritsch, P.; Klimant, I. Chem. Commun. 2013, 49, 2139.
[45] Aigner, D.; Freunberger, S. A.; Wilkening, M.; Saf, R.; Borisov, S. M.; Klimant, I. Anal. Chem. 2014, 86, 9293.
[46] Ma, Y.; Li, J.; Hou, S.; Zhang, J.; Shi, Z.; Jiang, T.; Wei, X. New J. Chem. 2016, 40, 6615.
[47] Ye, F.; Liang, X.; Wu, N.; Li, P.; Chai, Q.; Fu, Y. Spectrochim. Acta, Part A 2019, 216, 359.
[48] Georgiev, N. I.; Said, A. I.; Toshkova, R. A.; Tzoneva, D.; Bojinov, V. B, Dyes Pigm. 2019, 160, 28.
[49] Aigner, D.; Dmitriev, R. I.; Borisov, S. M.; Papkovsky, D. B.; Klimant, I. J. Mater. Chem. B 2014, 2, 6792.
[50] Zhang, W.; Gan, S. Y.; Li, F.; Han, D.; Zhang, Q.; Niu, L. RSC Adv. 2015, 5, 2207.
[51] Pacheco-Liňán, P.; Moral, M.; Nueda, M. L.; Cruz-Sánchez, R.; Fernández-Sainz, J.; Garzón-Ruiz, A.; Bravo, I.; Melguizo, M.; Laborda, J.; Albaladejo, J. Phys. Chem. C 2017, 121, 24786.
[52] You, S.; Cai, Q.; Müllen, K.; Yang, W.; Yin, M. Chem. Commun. 2014, 50, 823.
[53] Roy, A.; Saha, T.; Talukdar, P. Tetrahedron Lett. 2015, 56, 4975.
[54] Cho, E. J.; Yeo, H. M.; Ryu, B. J.; Jeong, H. A.; Nam, K. C. Bull. Korean Chem. Soc. 2006, 27, 1967.
[55] Chen, Z.; Wang, L.; Zou, G.; Zhang, L.; Zhang, G.; Cai, X.; Teng, M. Dyes Pigm. 2012, 94, 410.
[56] Li, G.; Zhao, Y.; Li, J.; Cao, J.; Zhu, J.; Sun, X.; Zhang, Q. J. Org. Chem. 2015, 80, 196.
[57] Wang, R.; Li, J.; Li, G.; Hao, C.; Zhang, Y.; Wang, S.; Zhao, J.; Liu, Q.; Shi, Z. Dyes Pigm. 2018, 156, 225.
[58] Maiti, D. K.; Roy, S.; Datta, A.; Banerjee, A. Chem. Phys. Lett. 2013, 588, 76.
[59] Googson, F.; Panda, D.; Ray, S.; Mitra, A.; Guha, S.; Saha, S. Org. Biomol. Chem. 2013, 11, 4797.
[60] Du, F.; Bao, Y.; Liu, B.; Tian, J.; Li, Q.; Bai, R. Chem. Commun. 2013, 49, 4631.
[61] Gao, T.; Zhou, W.; Zhao, Y.; Chang, W.; Musendo, R.; Chen, E.; Song, Y.; Ren, X. Chem. Commun. 2019, 55, 3012.
[62] Sudhakar, P.; Neena, K.; Thilagar, P. Dalton Trans. 2019, 48, 7218.
[63] Fu, Y.; Tang, H.; Liu, Z.; Zhang, W. X.; Ren, J. Chin. J. Org. Chem. 2018, 38, 1806(in Chinese). (付怡, 唐辉, 刘泽, 张万轩, 任君, 有机化学, 2018, 38, 1806.)
[64] Liu, Y.; Wang, K.; Guo, D.; Jiang, B. Adv. Funct. Mater. 2009, 19, 2230.
[65] Peng, H.; Ding, L.; Liu, T.; Chen, X.; Li, L.; Yin, S.; Fang, Y. Chem.-Asian J. 2012, 7, 1576.
[66] Zhang, J.; Liu, K.; Wang, G.; Shang, C.; Peng, H.; Liu, T.; Fang, Y. New J. Chem. 2018, 42, 12737.
[67] Hu, J.; Kuang, W.; Deng, K.; Zou, W.; Huang, Y.; Wei, Z.; Faul, C. F. J. Adv. Funct. Mater. 2012, 22, 4149.
[68] Deng, Q.; Zhou, E.; Huang, Y.; Qing, W.; Zhai, H.; Liu, Z.; Wei, Z. Chem. Commun. 2019, 55, 4379.
[69] Ji, S.; Wang, H.; Wang, T.; Yan, D. Adv. Mater. 2013, 25, 1755.
[70] Kalita, A.; Hussain, S.; Malik, A. H.; Subbarao, N. V. V.; Iyer, P. K. J. Mater. Chem. C 2015, 3, 10767.
[71] Huang, Y.; Liu, X.; Wang, Q.; Fu, J.; Zhao, L.; Liu, Z.; Jin, D. J. Mater. Chem. C 2017, 5, 7644.
[72] Wang, J.; He, E.; Liu, X.; Yu, L.; Wang, H.; Zhang, H.; Zhang, H. Sens. Actuators, B 2017, 239, 898.
[73] Wang, K.; Yang, H.; Qian, X.; Xue, Z.; Li, Y.; Liu, H.; Li, Y. Dalton Trans. 2014, 43, 11542.
[74] Liu, X.; Zhai, H.; Zhang, S.; Fu, J.; Huang, Y. Sens. Actuators, B 2017, 243, 500.
[75] Zhu, P.; Wang, Y.; Ma, P.; Li, S.; Fan, F.; Cui, K.; Ge, S.; Zhang, Y.; Yu, J. Anal. Chem. 2019, 91, 5591.
[76] Acikbas, Y.; Erdogan, M.; Capan, R.; Yukruk, F. Sens. Actuators, B 2014, 200, 61.
[77] Sun, Q.; Lü, Y.; Liu, L.; Liu, K.; Miao, R.; Fang, Y. ACS Appl. Mater. Interfaces 2016, 8, 29128.
[78] Abdalla, M. A.; Bayer, J.; Rädler, J. O.; Müllen, K. Angew. Chem., Int. Ed. 2004, 43, 3967.
[79] Aubert, Y.; Asseline, U. Org. Biomol. Chem. 2004, 2, 3496.
[80] Rahe, N.; Rinn, C.; Carell, T. Chem. Commun. 2003, 2120.
[81] Bevers, S.; Schutte, S.; Mclaughlin, L. W. J. Am. Chem. Soc. 2000, 122, 5905.
[82] Zheng, Y.; Long, H.; Schatz, G. C.; Lewis, F. D. Chem. Commun. 2005, 4795.
[83] Wagner, C.; Wagenknecht, H.-A. Org Lett. 2006, 8, 4191.
[84] Wang, Y.; Chen, J.; Jiao, H.; Chen, Y.; Li, W.; Zhang, Q.; Yu, C. Chem.-Eur. J. 2013, 19, 12846.
[85] Chen, J.; Jiao, H.; Li, W.; Liao, D.; Zhou, H.; Yu, C. Chem.-Asian J. 2013, 8, 276.
[86] Chen, X.; Jou, M. J.; Yoon, J. Org. Lett. 2009, 11, 2181.
[87] Yan, L.; Ye, Z.; Peng, C.; Zhang, S. Tetrahedron 2012, 68, 2725.
[88] Li, Y.; Yin, S.; Hou, J.; Meng, L.; Gao, M.; Sun, Y.; Zhang, C.; Bai, S.; Ren, J.; Yu, C. Analyst 2019, 144, 2034.
[89] Wang, K.; An, H.; Rong, Z.; Cao, Z.; Li, X. Biosens. Bioelectron. 2014, 58, 27.
[90] Lin, Y.; Chapman, R.; Stevens, M. M. Anal. Chem. 2014, 86, 6410.
[91] D'Autréaux, B.; Toledano, M. B. J. Nat. Rev. Mol. Cell Biol. 2007, 8, 813.
[92] Weinstain, R.; Savariar, E. N.; Felsen, C N.; Tsien, R. Y. J. Am. Chem. Soc. 2014, 136, 874.
[93] Sundaresan, M.; Yu, Z.; Finkel, T. Science 1995, 270, 296.
[94] Ohshima, H.; Tatemichi, M.; Sawa, T. J. Arch. Biochem. Biophys. 2003, 417, 3.
[95] Shah, A. M.; Channon, K. M. J. Heart 2004, 90, 486.
[96] Barnham, K. J.; Masters, C. L.; Bush, A. I. Nat. Rev. Drug Discovery 2004, 3, 205.
[97] Soh, N.; Ariyoshi, T.; Fukaminato, T.; Nakano, K.; Irie, M.; Imato, T. Bioorg. Med. Chem. Lett. 2006, 16, 2943.
[98] Soh, N.; Ariyoshi, T.; Fukaminato, T.; Nakajima, H.; Nakano, K.; Imato, T. Org. Biomol. Chem. 2007, 5, 3762.
[99] Maki, T.; Soh, N.; Fukaminato, T.; Nakajima, H.; Nakano, K.; Imato, T. Anal. Chim. Acta 2009, 639, 78.
[100] Kaloyanova, S.; Zagraanyarski, Y.; Ritz, S.; Hanulová, M.; Koynov, K.; Vonderheit, A.; Müllen, K.; Peneva, K, J. Am. Chem. Soc. 2016, 138, 2881.
[101] Ou, Z.; Feng, Z.; Liu, G.; Chen, Y.; Gao, Y.; Li, Y.; Wang, X. Chem. Lett. 2015, 44, 425.
[102] Gao, Y.-Y.; Cai, W. J.; Ou, Z. Z.; Ma, T. T.; Wang, Z. J.; Xu, M. H. Imaging Sci. Photochem. 2017, 35, 552(in Chinese). (高云燕, 蔡温姣, 欧植泽, 马拖拖, 王子继, 许墨横, 影像科学与光化学, 2017, 35, 552.)
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