Citation: SUN Dan, YUAN Xue-Mei, XU Hai-Jun, XU Li, SHEN Zhen. Progress on Near-infrared Fluorescent BODIPY Dyes[J]. Chinese Journal of Inorganic Chemistry, ;2015, 31(8): 1467-1479. doi: 10.11862/CJIC.2015.209 shu

Progress on Near-infrared Fluorescent BODIPY Dyes

SUN Dan ¹ ,
YUAN Xue-Mei ¹ ,
XU Hai-Jun ^1,2,, ,
XU Li ³ ,
SHEN Zhen ^2,,

1.
1. College of Chemical Engineering, Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, Nanjing Forestry University, Nanjing 210037, China;
2.
2. State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, China;
3.
3. Advanced Analysis and Testing Center, Nanjing Forestry University, Nanjing 210037, China

Corresponding author: XU Hai-Jun, SHEN Zhen,
Received Date: 21 February 2015
Available Online: 21 May 2015
Fund Project: 国家自然科学基金(No.21301092,21371090) (No.21301092,21371090)霍英东教育基金会(No.141030) (No.141030)江苏省自然科学基金(No.BK20130054) (No.BK20130054)江苏省生物质绿色燃料与化学品重点实验室开放基金(No.JSBGFC12002) (No.JSBGFC12002)

Near-infrared (NIR) fluorescent dyes based-on boron difluoride dipyrromethene (BODIPY) are a new type of fluorescent dyes, which have been widely studied because of their excellent photophysical and photochemical properties and have become a newly-emerging hotspot in recent years. In this review article, we summarize the latest research progresses in the design, synthesis and application of near-infrared fluorescent BODIPYs, in addition their future research aspects and application perspectives are also prospected.
- boron dipyrromethene;near-infrared (NIR);fluorescent dyes;photoelectric functional materials
1. [1]
  [1] Frangioni J V. Curr. Opin. Chem. Biol., 2003,7:626-634
2. [2]
  [2] Ntziachristos V, Bremer C, Weissleder R. Eur. Radiol., 2003, 13:195-208
3. [3]
  [3] LIU Zheng(刘政), SUN Li-Ning(孙丽宁), SHI Li-Yi(施利毅), et al. Progress in Chemistry(化学进展), 2011,23(1):153-164
4. [4]
  [4] Jin Y, Ye F, Zeigler M, et al. ACS Nano, 2011,5(2):1468-1475
5. [5]
  [5] Yuan L, Lin W Y, Zheng K B, et al. Chem. Soc. Rev., 2013,42(24):622-661
6. [6]
  [6] Qian G, Wang Z Y. Chem. Asian J., 2010,5(5):1006-1029
7. [7]
  [7] Pogue B, Jiang S D, Dehghani H. Alternative Breast Imaging. Chapter 10. Boston:Springer, 2005:201-226
8. [8]
  [8] Lu H, Mack J, Yang Y, et al. Chem. Soc. Rev., 2014,43:4778-4823
9. [9]
  [9] Ulrich G, Goeb S, Nicola D A, et al. J. Org. Chem., 2011,76(11):4489-4505
10. [10]
  [10] WANG Cui-Ping(王红萍), CUI Ai-Jun(崔爱军), TIAN Mao-Zhong(田茂忠), et al. Contemp. Chem. Ind.(当代化工), 2007,36(2):198-201
11. [11]
  [11] Karolin J, Johansson L B A, Strandberg L. J. Am. Chem. Soc., 1994,116(17):7801-7806
12. [12]
  [12] Ulrich G, Ziessel R, Harriman A. Angew. Chem. Int. Ed., 2008,47(7):1184-1201
13. [13]
  [13] Loudet A, Burgess K. Chem. Rev., 2007,107(11):4891-4932
14. [14]
  [14] Gabe Y, Urano Y, Kikuchi K, et al. J. Am. Chem. Soc., 2004,126(10):3357-3367
15. [15]
  [15] Wang Y W, Descalzo A B, Shen Z, et al. Chem. Eur. J., 2010,16(9):2887-2903
16. [16]
  [16] Rurack K, Kollmannsberger M, Daub J. Angew. Chem. Int. Ed., 2001,40(2):385-387
17. [17]
  [17] Yu C J, Xu Y J, Jiao L J, et al. Chem. Eur. J., 2012,18(21):6437-6442
18. [18]
  [18] Ono N, Yamamoto T, Shimada N, et al. Heterocycles, 2003, 61(1):433-447
19. [19]
  [19] Shen Z, Rhr H, Rurack K, et al. Chem. Eur. J., 2004,10(19):4853-4871
20. [20]
  [20] Uppal T, Hu X K, Fronczek F R, et al. Chem. Eur. J., 2012, 18(13):3893-3905
21. [21]
  [21] Descalzo A B, Xu H J, Xue Z L, et al. Org. Lett., 2008,10(8):1581-1584
22. [22]
  [22] Okujima T, Tomimori Y, Nakamura J, et al. Tetrahedron, 2010,66(34):6895-6900
23. [23]
  [23] Nakamura M, Tahara H, Takahashi K, et al. Org. Biomol. Chem., 2012,10(34):6840-6849
24. [24]
  [24] Nakamura M, Kitatsuka M, Takahashi K, et al. Org. Biomol. Chem., 2014,12(8):1309-1317
25. [25]
  [25] Deniz E, Isbasar G C, Bozdemir A, et al. Org. Lett., 2008,10(16):3401-3403
26. [26]
  [26] Lu J S, Fu H Y, Zhang Y G, et al. Angew. Chem. Int. Ed., 2011,50(49):11658-11662
27. [27]
  [27] Olivier J H, Widmaier J, Ziessel R. Chem. Eur. J., 2011,17(42):11709-11714
28. [28]
  [28] Ziessel R, Rihn S, Harriman A. Chem. Eur. J., 2010,16(39):11942-11953
29. [29]
  [29] Zhao Y, Zhang Y, Lü X, et al. J. Mater. Chem., 2011,21(35):13168-13171
30. [30]
  [30] Shandura M P, Yakubovskyi V P, Gerasov A O, et al. Eur. J. Org. Chem., 2012,9:1825-1834
31. [31]
  [31] He H, Lo P C, Yeung S L, et al. J. Med. Chem., 2011,54(8):3097-3102
32. [32]
  [32] Zhang D K, Wen Y G, Xiao Y, et al. Chem. Commun., 2008, 49:4777-4779
33. [33]
  [33] Lai R Y, Bard A J. J. Phys. Chem. B, 2003,107(21):5036-5042
34. [34]
  [34] Zhang D K, Wang Y C, Xiao Y, et al. Tetrahedron, 2009,65(39):8099-8103
35. [35]
  [35] Xiao Y, Zhang D K, Qian X H, et al. Chem. Commun., 2011,47:11513-11515
36. [36]
  [36] Lu H, Wang Q H, Gai L Z, et al. Chem. Eur. J., 2012,18(25):7852-7861
37. [37]
  [37] Lin H Y, Huang W C, Chen Y C, et al. Chem. Commun., 2012,48:8913-8915
38. [38]
  [38] Fu G L, Pan H, Zhao Y H, et al. Org. Biomol. Chem., 2011, 9(23):8141-8146
39. [39]
  [39] Umezawa K, Nakamura Y, Makino H, et al. J. Am. Chem. Soc., 2008,130(5):1550-1551
40. [40]
  [40] Umezawa K, Matsui A, Nakamura Y, et al. Chem. Eur. J., 2009,15(5):1096-1106
41. [41]
  [41] Wang H, Zeng J. Can. J. Chem., 2009,87(9):1209-1212
42. [42]
  [42] Awuah S G, Polreis J, Biradar V, et al. Org. Lett., 2011,13(15):3884-3887
43. [43]
  [43] Matsui A, Umezawa K, Shindo Y, et al. Chem. Commun., 2011,47:10407-10409
44. [44]
  [44] Hayashi Y, Obata N, Tamaru M, et al. Org. Lett., 2012,14(3):866-869
45. [45]
  [45] Yang Y C, Guo Q L, Chen H C, et al. Chem. Commun., 2013,49:3940-3942
46. [46]
  [46] Yakubovskyi V P, Shandura M P, Kovtun Y P. Eur. J. Org. Chem., 2009,19:3237-3243
47. [47]
  [47] Jiao C, Huang K W, Wu J. Org. Lett., 2011,13(4):632-635
48. [48]
  [48] Jiao C, Zhu L, Wu J. Chem. Eur. J., 2011,17(24):6610-6614
49. [49]
  [49] Zeng L, Jiao C, Huang X, et al. Org. Lett., 2011,13(22):6026-6029
50. [50]
  [50] Killoran J, Allen L, Gallagher J F, et al. Chem. Commun., 2002,17:1862-1863
51. [51]
  [51] Byrne A T, OConnor A E, Hall M, et al. Br. J. Cancer, 2009, 101:1565-1573
52. [52]
  [52] Zhao W, Carreira E M. Angew. Chem. Int. Ed., 2005,44(11):1677-1679
53. [53]
  [53] Zhang X, Yu H, Xiao Y. J. Org. Chem., 2012,77(1):669-673
54. [54]
  [54] Gresser R, Hartmann H, Wrackmeyer M, et al. Tetrahedron, 2011,67(37):7148-7155
55. [55]
  [55] Donyagina V F, Shimizu S, Kobayashi N, et al. Tetrahedron Lett., 2008,49(42):6152-6154
56. [56]
  [56] Gresser R, Hummert M, Hartmann H, et al. Chem. Eur. J., 2011,17(10):2939-2947
57. [57]
  [57] Lu H, Shimizu S, Mack J, et al. Chem. Asian J., 2011,6(4):1026-1037
58. [58]
  [58] Adarsh N, Shanmugasundaram M, Avirah R R, et al. Chem. Eur. J., 2012,18(40):12655-12662
1. [1]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
2. [2]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
3. [3]
  Xiaoning TANG , Shu XIA , Jie LEI , Xingfu YANG , Qiuyang LUO , Junnan LIU , An XUE . Fluorine-doped MnO₂ with oxygen vacancy for stabilizing Zn-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1671-1678. doi: 10.11862/CJIC.20240149
4. [4]
  Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
5. [5]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
6. [6]
  Xin XIONG , Qian CHEN , Quan XIE . First principles study of the photoelectric properties and magnetism of La and Yb doped AlN. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1519-1527. doi: 10.11862/CJIC.20240064
7. [7]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
8. [8]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
9. [9]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
10. [10]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
11. [11]
  Qiangqiang SUN , Pengcheng ZHAO , Ruoyu WU , Baoyue CAO . Multistage microporous bifunctional catalyst constructed by P-doped nickel-based sulfide ultra-thin nanosheets for energy-efficient hydrogen production from water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1151-1161. doi: 10.11862/CJIC.20230454
12. [12]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
13. [13]
  Cheng PENG , Jianwei WEI , Yating CHEN , Nan HU , Hui ZENG . First principles investigation about interference effects of electronic and optical properties of inorganic and lead-free perovskite Cs₃Bi₂X₉ (X=Cl, Br, I). Chinese Journal of Inorganic Chemistry, 2024, 40(3): 555-560. doi: 10.11862/CJIC.20230282
14. [14]
  Juntao Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-. doi: 10.3866/PKU.WHXB202312024
15. [15]
  Ming ZHENG , Yixiao ZHANG , Jian YANG , Pengfei GUAN , Xiudong LI . Energy storage and photoluminescence properties of Sm³⁺-doped Ba_0.85Ca_0.15Ti_0.90Zr_0.10O₃ lead-free multifunctional ferroelectric ceramics. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 686-692. doi: 10.11862/CJIC.20230388
16. [16]
  Xinxin JING , Weiduo WANG , Hesu MO , Peng TAN , Zhigang CHEN , Zhengying WU , Linbing SUN . Research progress on photothermal materials and their application in solar desalination. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1033-1064. doi: 10.11862/CJIC.20230371
17. [17]
  Doudou Qin , Junyang Ding , Chu Liang , Qian Liu , Ligang Feng , Yang Luo , Guangzhi Hu , Jun Luo , Xijun Liu . Addressing Challenges and Enhancing Performance of Manganese-based Cathode Materials in Aqueous Zinc-Ion Batteries. Acta Physico-Chimica Sinica, 2024, 40(10): 2310034-. doi: 10.3866/PKU.WHXB202310034
18. [18]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
19. [19]
  Jiahong ZHENG , Jiajun SHEN , Xin BAI . Preparation and electrochemical properties of nickel foam loaded NiMoO₄/NiMoS₄ composites. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 581-590. doi: 10.11862/CJIC.20230253
20. [20]
  Limei CHEN , Mengfei ZHAO , Lin CHEN , Ding LI , Wei LI , Weiye HAN , Hongbin WANG . Preparation and performance of paraffin/alkali modified diatomite/expanded graphite composite phase change thermal storage material. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 533-543. doi: 10.11862/CJIC.20230312

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(447)
HTML views(123)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142