中文
Announcement
More
Progress in Chemistry 2006, Vol. 18 Issue (0203): 252-261 Previous Articles   Next Articles

• Review •

Synthesis and Applications of Rhodamine Fluorescent Dyes

Fanyong Yan1; Ligong Chen1*; Xilong Yan1; Fengyan Ge1; Erhong Duan2   

  1. 1.College of Chemical Engineering, Tianjin University, Tianjin 300072, China;2. R&D Center for Petrochemical Technology, Tianjin University, Tianjin 300072, China 
  • Received: Revised: Online: Published:
  • Contact: Ligong Chen
PDF ( 12188 ) Cited
Export

EndNote

Ris

BibTeX

The recent progress in the studies on rhodamines is reviewed. The structure, design idea, synthesis, effects and applications of rhodamines are discussed in detail.

CLC Number: 

[ 1 ] Haugland R P. Handbook of Fluorescent Probes and Research Chemicals , 9th ed. Eugene OR: Molecular Probes , 2002. 6 —18
[ 2 ] 黄晓峰(Huang X F) , 张远强(Zhang Y Q) , 张英起(Zhang Y Q) . 荧光探针技术( Fluorescence Probe Technology) . 北京(Beijing) : 人民军医出版社(People′s Military Medical Press) ,2004. 49 —53
[ 3 ] Lefevre C , Kang H C , Haugland R P , et al . Bioconj . Chem. ,1996 , 7 (4) : 482 —489
[ 4 ] 吴世康(Wu S K) . 化学进展(Progress in Chemistry) , 1996 , 8(2) : 118 —128
[ 5 ] 杨丙成(Yang B C) , 关亚风(Guan Y F) , 谭峰(Tan F) . 化学进展(Progress in Chemistry) , 2004 , 16 (6) : 871 —878
[ 6 ] 张华山(Zhang H S) , 王红(Wang H) , 赵嫒嫒(Zhao Y Y) . 分子探针与检测试剂(Molecular Probe &Detect Reagent) . 北京(Beijing) : 科学出版社(Science Press) , 2002. 326
[ 7 ] Dela Cruz J L , Blanchard G J . J . Phys. Chem. A , 2002 , 106(44) : 10718 —10724
[ 8 ] Ikeda H , Saito I , Kitagawa F. US 2004 101 839 , 2004
[ 9 ] Zhang Y Z, Haugland R P. US 5 868 261 , 1997
[10] Ghanadzadeh A , Zanjanchi M A. Spectrochimica Acta Part A ,2001 , 57 (9) : 1865 —1871
[11] Ghanadzadeh A , Sariri R , Bahrpaima K. Spectrochimica Acta Part A , 2001 , 57 (1) : 155 —161
[12] Meallier P , Moullet M, Chabaud F , et al . Dyes Pigm. , 1998 , 36(2) : 161 —167
[13] Ferguson M W, Beaumont P C , Jones S E , et al . Phys. Chem.Chem. Phys. , 1999 , 1 (2) : 261 —268
[14] Kang H C. US 5 846 737 , 1998
[15] Nguyen T, FrancisMB. Organic Letters. , 2003 , 5 (18) : 3245 —3248
[16] Haugland R P , Singer V L , Yue S T. US 6 399 392 , 2002
[17] Waggoner A S. “Fluorescent Probes for Cytometry”in Flow Cytometry and Sorting , 2nd ed. Wiley-Liss , 1990. 209 —225
[18] Vinayak R. Tetrahedron Lett . , 1999 , 40 (43) : 7611 —7613
[19] Rigler R , Widengren J , Mets U. Fluorescence Spectroscopy.Berlin : Springer , 1992. 13
[20] Keller R A , Ambrose W P , Goodwin P M, et al . Appl .Spectrosc. , 1996 , 50 (7) : 12A —32A
[21] Kohn F , Hofkens J , de Schryver F C. Chem. Phys. Lett . , 2000 ,321 (5/6) : 372 —378
[22] Renge I. J . Phys. Chem. A , 2001 , 105 (40) : 9094 —9103
[23] Pevenage D , van der Auveraer M, de Schryver F C. Langmuir ,1999 , 15 (24) : 8465 —8473
[24] Houghten R A , Dooly C T, Appel J R. Bioorg. Med. Chem.Lett . , 2004 , 14 (8) : 1947 —1951
[25] Gee K R , Weinberg Eric S , Kozlowski D J . Bioorganic & Medicinal Chemistry Lett . , 2001 , 11 (16) : 2181 —2183
[26] Rucker V C , Foister S , Melander C , et al . J . Am. Chem. Soc. ,2003 , 125 : 1195 —1202
[27] Rucker V C , Dunn A R , Sharma S , et al . J . Phys. Chem. B ,2004 , 108 : 7490 —7494
[28] Breitenkamp K, Emrick T. J . Am. Chem. Soc. , 2003 , 125 :12070 —12071
[29] Rao T S , Zhang W, Xiao H , et al . Nucleosides , Nucleotides & Nucleic Acid , 2003 , 22 (5/8) : 1443 —1445
[30] Sando S , Abe H , Kool E T. J . Am. Chem. Soc. , 2004 , 126 :1081 —1087
[31] Smith GA. J . Chem. Soc. , Perkin Trans. Ⅱ, 1993 , 1195
[32] Berman E M, Hollis Showalter H D. J . Org. Chem. , 1989 , 54(23) : 5642 —5644
[33] Scala-Valéro C , Doizi D , Guillaumet G. Tetrahedron Lett . ,1999 , 40 (26) : 4803 —4806
[34] Mao F , Leung W Y, Haugland R P. US 6 130 101 , 2000
[35] Denis G, Abdelkrim H. US 0 212 126 , 2003
[36] Louis G, Villeneuve L , Glasson R , et al . US 5 773 460 , 1998
[37] 吴世康(Wu S K) . 化学进展( Progress in Chemistry) , 2005 ,17 (1) : 15 —39
[38] Bell K H , McCaffery L F. Australian J . Chem. , 1994 , 47 (10) :1925 —1933
[39] Benson S C , Lam J Y L , Upadhya K G, et al . US 5 936 087 ,1999
[40] Lam J Y L , Benson S C , Menchen S M. US 6 248 884 , 2001
[41] Sauer M, Han K T, Drexhage K H , et al . J . Fluoresc. , 1995 , 5(3) : 247 —261
[42] Drexhage K H , Martin G. Laser Focus , 1973 , 9 (3) : 35 —39
[43] Panchuk-Voloshina N , Haugland R P , Bishop-Stewart J . J .Histochem. &Cytochem. , 1999 , 47 (9) : 1179 —1188
[44] Herrmann R , Josel H P , Drexhage K H , et al . US 5 750 409 ,1998
[45] Lee L G, Graham R J , Werner W E , et al . US 6 372 907B1 ,2002
[46] Hammond P R. US 4 622 400 , 1986
[47] Liu J X, Diwu Z J , Haugland R P , et al . WO 0 212 195 , 2002
[48] Liu J X, Diwu Z J , Haugland R P , et al . Tetrahedron Lett . ,2003 , 44 (23) : 4355 —4359
[49] Hammond P R , Feeman J F , Field G F , et al . US 5 792 389 ,1998
[50] Hammond P R , Feeman J F. US 4 945 176 , 1990
[51] Liu J , Bhalgat M, Zhang C , et al . Bioorg. Med. Chem. Lett . ,1999 , 9 (22) : 3231 —3236
[52] Cai S X, Zhang H Z, Guastella J , et al . Bioorganic &Medicinal Chemistry Lett . , 2001 , 11 (1) : 39 —42
[53] Alder A , Barnard S M, Beckelmann D , et al . WO 9 711 067 ,1997
[54] Alder A , Barnard S. EP 623 599 , 1994
[55] Corries J E T, Trentham D R. US 5 434 272 , 1995
[56] Gee K R , Sun W C , Haugland R P , et al . Tetrahedron Lett . ,1996 , 37 (44) : 7905 —7908
[57] Josel H P , Herrmann R , Drexhage K H. US 6 184 379 , 2001
[58] Lee L , Benson S C , Rosenblum B B , et al . US 5 847 162 , 1998
[59] Burgess K, Burghart A , Chen J . Proc. SPIE Int . Soc. Opt .Eng. , 2000 , 3926 : 95 —105
[60] Burghart A , Thoresen L H , Chen J , et al . Chem. Commun. ,2000 , 2203 —2204
[61] Zhang Y Z, Haugland R P. US 5 686 261 , 1997
[62] Jiao G S , Castro J C , Thoresen L H. Organic Lett . , 2003 , 5(20) : 3675 —3677
[63] Corrie J E T, Craik J S. WO 9 509 170 , 1995
[64] Hideji I , Hisayuki K, Shigeaki M, et al . JP 103 975 (A) , 2000
[65] Nagano T, Kojima H. US 6 201 134 , 2001
[66] Kojima H , Hirotani M, Nagano T, et al . Anal . Chem. , 2001 ,73 (9) : 1967 —1973
[67] Nagano T, Kojima H , Kikuchi K. US 0 147 035 , 2004
[68] Hoekstra D , de Boer T, Klappe K, et al . Biochem. , 1984 , 23(24) : 5675 —5681
[69] Macdonald R I. J . Biol . Chem. , 1990 , 265 ( 23) : 13533 —13539
[70] Pozzi D , Lisi A , de Ros I , et al . Photochem. Photobiol . , 1993 ,57 (3) :426 —430
[71] Ramos S S , Vihena A F , Santos L , et al . Magn. Reson. Chem. ,2000 , 38 (6) : 475 —478
[72] Gaboury L , Giasson R , Li T, et al . US 5 556 992 , 1996
[73] Gaboury L , Giasson R , Li T, et al . US 5 773 460 , 1996
[74] 顾新华(Gu X H) , 戴光松(Dai G S) , 吴世康(Wu S K) . 感光科学与光化学( Photograph. Sci . Photochem. ) , 1995 , 13(1) : 78 —82
[75] Costela A , Arbeloa T L , Moreno I G, et al . J . Appl . Phys. ,1996 , 80 (6) : 3167 —3173
[76] Arbeloa T L , Costela A , Garcia I , et al . J . Lumin. , 1997 , 75(4) : 309 —317
[77] Arbeloa F L , Arbeloa T L , Costela A. Applied Physics B : Lasers and Optics , 1998 , 64 (6) : 651 —657
[78] Miljanic S , Cimerman Z, Frkanec L , et al . Analytica Chimica Acta , 2002 , 468 (1) : 13 —25
[79] Mayer U , Oberlinner A. US 4 647 675 , 1978
[80] Chiarello R H , Liu W, Yokabata K E. US 6 750 357B1 , 2004
[81] Drexhage K H , Jutta A J , Monika H S. WO 055 117A2 , 2002
[82] Dujols V , Ford F , Czarnik A W. J . Am. Chem. Soc. , 1997 ,119 (31) : 7386 —7387
[83] Thomas R , Sasamoto K. Anal . Commun. , 1998 , 35 (6) : 195 —197
[84] Yang X F , Guo X Q , Zhao YB. Talanta , 2002 , 57 (5) : 883 —890
[85] Arnost M J , Meneghinl F A , Palumbo P S , et al . EP 0 285 179 ,1988
[86] Morrison L E , Wang Y, Ju J , et al . Anal . Chem. , 1995 , 67(7) : 1197 —1203
[87] Haugland R P , Szalecki W. US 5 798 276 , 1998
[88] Tian H. J . Photochem. Photobiol . A: Chem. , 1995 , 91 : 125 —130
[89] Tian H , He Y, Chang C P. J . Mater. Chem. , 2000 , 10 (9) :2049 —2055
[90] Drexhage K H , Arden J , Deltau G. J . Lumi . , 1991 , 48/49 (1) :352 —358
[91] Tian H , Tang Y F , Chen K C. Dyes Pigm. , 1994 , 26 ( 3) :159 —165
[92] Tian H , Su J H , Chen K C , et al . Photogr. Sci . Photochem. ,1996 , 14 (4) : 355 —359
[93] Su J H , Tian H , Chen KC. Dyes Pigm. , 1996 , 31 (1) : 69 —77
[94] Pevenage D , van der Auweraer M, de Schryver F C. Chem.Phys. Lett . , 2000 , 319 (5/6) : 512 —520
[95] Huglin D , Seiffert W, Zimmermann H W. J . Photochem.Photobiol . B : Biology , 1995 , 31 (3) : 145 —158
[96] Ribou A C , Vigo J , Salmon J M. J . Photochem. Photobiol . A:Chem. , 2002 , 151 (1/3) : 49 —55
[97] Adam G C , Vanderwal C D , Sorensen E J , et al . Angew. Chem.Int . Ed. , 2003 , 42 : 5480 —5484
[98] Jiao G S , Thoresen L H , Burgess K. J . Am. Chem. Soc. ,2003 , 125 : 14668 —14669
[99] Han J W, Castro J C , Burgess K. Tetrahedron Letters , 2003 , 44 :9359 —9362

[1] Jing He, Jia Chen, Hongdeng Qiu. Synthesis of Traditional Chinese Medicines-Derived Carbon Dots for Bioimaging and Therapeutics [J]. Progress in Chemistry, 2023, 35(5): 655-682.
[2] Jianfeng Yan, Jindong Xu, Ruiying Zhang, Pin Zhou, Yaofeng Yuan, Yuanming Li. Nanocarbon Molecules — the Fascination of Synthetic Chemistry [J]. Progress in Chemistry, 2023, 35(5): 699-708.
[3] Xinyue Wang, Kang Jin. Chemical Synthesis of Peptides and Proteins [J]. Progress in Chemistry, 2023, 35(4): 526-542.
[4] Liu Yvfei, Zhang Mi, Lu Meng, Lan Yaqian. Covalent Organic Frameworks for Photocatalytic CO2 Reduction [J]. Progress in Chemistry, 2023, 35(3): 349-359.
[5] Zixuan Liao, Yuhui Wang, Jianping Zheng. Research Advance of Carbon-Dots Based Hydrophilic Room Temperature Phosphorescent Composites [J]. Progress in Chemistry, 2023, 35(2): 263-373.
[6] Yehjun Lim, Yanmei Li. Chemical Synthesis/Semisynthesis of Post-Translational Modified Tau Protein [J]. Progress in Chemistry, 2022, 34(8): 1645-1660.
[7] Peng Xu, Biao Yu. Challenges in Chemical Synthesis of Glycans and the Possible Problems Relevant to Condensed Matter Chemistry [J]. Progress in Chemistry, 2022, 34(7): 1548-1553.
[8] Deshan Zhang, Chenho Tung, Lizhu Wu. Artificial Photosynthesis [J]. Progress in Chemistry, 2022, 34(7): 1590-1599.
[9] Shuaiwei Peng, Zhuofu Tang, Bing Lei, Zhiyuan Feng, Honglei Guo, Guozhe Meng. Design and Application of Bionic Surface for Directional Liquid Transportation [J]. Progress in Chemistry, 2022, 34(6): 1321-1336.
[10] Fangyuan Li, Junhao Li, Yujie Wu, Kaixiang Shi, Quanbing Liu, Hongjie Peng. Design and Preparation of Electrode Nanomaterials with “Yolk-Shell”Structure for Lithium/Sodium-Ion/Lithium-Sulfur Batteries [J]. Progress in Chemistry, 2022, 34(6): 1369-1383.
[11] Shiyu Li, Yongguang Yin, Jianbo Shi, Guibin Jiang. Application of Covalent Organic Frameworks in Adsorptive Removal of Divalent Mercury from Water [J]. Progress in Chemistry, 2022, 34(5): 1017-1025.
[12] Xiaoqing Ma. Graphynes for Photocatalytic and Photoelectrochemical Applications [J]. Progress in Chemistry, 2022, 34(5): 1042-1060.
[13] Xiuli Shao, Siqi Wang, Xuan Zhang, Jun Li, Ningning Wang, Zheng Wang, Zhongyong Yuan. Fabrication and Application of MFI Zeolite Nanosheets [J]. Progress in Chemistry, 2022, 34(12): 2651-2666.
[14] Xueer Cai, Meiling Jian, Shaohong Zhou, Zefeng Wang, Kemin Wang, Jianbo Liu. Chemical Construction of Artificial Cells and Their Biomedical Applications [J]. Progress in Chemistry, 2022, 34(11): 2462-2475.
[15] Baoyou Yan, Xufei Li, Weiqiu Huang, Xinya Wang, Zhen Zhang, Bing Zhu. Synthesis of Metal-Organic Framework-NH2/CHO and Its Application in Adsorption Separation [J]. Progress in Chemistry, 2022, 34(11): 2417-2431.