Research Progress on Application of Fluorescent Sensors Based on Squaraine Dyes
- Corresponding author: XU Yongqian, xuyq@nwsuaf.edu.cn
Citation:
SHI Weining, XU Yongqian, SUN Shiguo, LI Hongjuan. Research Progress on Application of Fluorescent Sensors Based on Squaraine Dyes[J]. Chinese Journal of Applied Chemistry,
;2017, 34(12): 1433-1449.
doi:
10.11944/j.issn.1000-0518.2017.12.170327
Guo Z Q, Park S, Yoon J Y. Recent Progress in the Development of Near-Infrared Fluorescent Probes for Bioimaging Applications[J]. Chem Soc Rev, 2014,43(1):16-29. doi: 10.1039/C3CS60271K
Yuan L, Lin W Y, Zheng K B. Far-red to Near Infrared Analyte-Responsive Fluorescent Probes Based on Organic Fluorophore Platforms for Fluorescence Imaging[J]. Chem Soc Rev, 2013,42(2):622-661. doi: 10.1039/C2CS35313J
Takeda N, Parkinson B A. The Relationship Between Squaraine Dye Surface Morphology and Sensitization Behavior on SnS 2 Electrodes[J]. Electrochim Acta, 2000,45(28):4559-4564. doi: 10.1016/S0013-4686(00)00607-1
Tam A C. Optoacoustic Determination of Photocarrier Generation Efficiencies of Dye Films[J]. Appl Phys Lett, 1980,37(11):978-981. doi: 10.1063/1.91725
Law K Y, Bailey F C. Squaraine Chemistry:Effect of Synthesis on the Morphological and Xerographic Properties of Photoconductive Squaraines[J]. J Imaging Sci Technol, 1987,31(4):172-177.
Merritt V Y, Hovel H J. Organic Solar Cells of Hydroxy Squarylium[J]. Appl Phys Lett, 1976,29(7):414-415. doi: 10.1063/1.89101
Loutfy R O, Hsiao C K, Kazmaier P M. Photoconductivity of Organic Particle Dispersions-Squaraine Dyes[J]. Photogr Sci Eng, 1983,27(1):5-9.
Gravesteijn D J, Steenbergen C, Veen J V D. Single Wavelength Optical Recording in Pure, Solvent Coated Infrared Dye Layers[J]. Proc SPIE Int Soc Opt Eng, 1983,420(6):327-331.
Dirk C W, Kuzyk M G. Squarylium Dye-doped Polymer Systems as Quadratic Electrooptic Materials[J]. Chem Mater, 1990,2(1):4-6. doi: 10.1021/cm00007a002
Kuzyk M G, Paek U C, Dirk C W. Guest-host Polymer Fibers for Nonlinear Optics[J]. Appl Phys Lett, 1991,59(8):902-904. doi: 10.1063/1.105271
Chen C T, Marder S R, Cheng L T. Molecular First Hyperpolarizabilities of a New Class of Asymmetric Squaraine Dyes[J]. J Chem Soc, Chem Commun, 1994(3):259-260. doi: 10.1039/c39940000259
Jyothish K, Hariharan M, Ramaiah D. Chiral Supramolecular Assemblies of a Squaraine Dye in Solution and Thin Films:Concentration, Temperature, and Solvent-induced Chirality Inversion[J]. Chem-Eur J, 2007,13(20):5944-5951. doi: 10.1002/(ISSN)1521-3765
Zhang D, Zhao Y X, Qiao Z Y. Nano-confined Squaraine Dye Assemblies:New Photoacoustic and Near-Infrared Fluorescence Dual-Modular Imaging Probes in vivo[J]. Bioconjugate Chem, 2014,25(11):2021-2029. doi: 10.1021/bc5003983
Johnson J R, Fu N, Arunkumar E. Squaraine Rotaxanes:Superior Substitutes for Cy-5 in Molecular Probes for Near-Infrared Fluorescence Cell Imaging[J]. Angew Chem, 2007,119(29):5624-5627. doi: 10.1002/(ISSN)1521-3757
Gassensmith J J, Arunkumar E, Barr L. Self-Assembly of Fluorescent Inclusion Complexes in Competitive Media Including the Interior of Living Cells[J]. J Am Chem Soc, 2007,129(48):15054-15059. doi: 10.1021/ja075567v
Thomas J, Sherman D B, Amiss T J. Synthesis and Biosensor Performance of a Near-IR Thiol-Reactive Fluorophore Based on Benzothiazolium Squaraine[J]. Bioconjugate Chem, 2007,18(6):1841-1846. doi: 10.1021/bc700146r
Ros-Lis J V, García B, Jiménez D. Squaraines as Fluoro-Chromogenic Probes for Thiol-Containing Compounds and Their Application to the Detection of Biorelevant Thiols[J]. J Am Chem Soc, 2004,126(13):4064-4065. doi: 10.1021/ja031987i
Snee P T, Somers R C, Nair G. A Ratiometric CdSe/ZnS Nanocrystal pH Sensor[J]. J Am Chem Soc, 2006,128(41):13320-13321. doi: 10.1021/ja0618999
Arunkumar E, Chithra P, Ajayaghosh A. A Controlled Supramolecular Approach Toward Cation-Specific Chemosensors:Alkaline Earth Metal Ion-Driven Exciton Signaling in Squaraine Tethered Podands[J]. J Am Chem Soc, 2004,126(21):6590-6598. doi: 10.1021/ja0393776
Das S, Thomas K G, Ramanathan R. Photochemistry of Squaraine Dyes.6.Solvent Hydrogen Bonding Effects on the Photophysical Properties of Bis (Benzothiazolylidene) Squaraines[J]. J Phys Chem, 1993,97(51):13625-13628. doi: 10.1021/j100153a033
Zhai D T, Xu W, Zhang L Y. The Role of "Disaggregation" in Optical Probe Development[J]. Chem Soc Rev, 2014,43(8):2402-2411. doi: 10.1039/c3cs60368g
Li B H, Li W W, Xu Y Q. A Simple Approach for the Discrimination of Surfactants Based on the Control of Squaraine Aggregation[J]. Chem Commun, 2015,51(78):14652-14655. doi: 10.1039/C5CC06086A
Volkova K D, Kovalska V B, Tatarets A L. Spectroscopic Study of Squaraines as Protein-Sensitive Fluorescent Dyes[J]. Dyes Pigm, 2007,72(3):285-292. doi: 10.1016/j.dyepig.2005.09.007
Wang B S, Fan J L, Sun S G. 1-(Carbamoylmethyl)-3H-indolium Squaraine Dyes:Synthesis, Spectra, Photo-Stability and Association with BSA[J]. Dyes Pigm, 2010,85(1):43-50.
Xu Y Q, Li Z Y, Malkovskiy A. Aggregation Control of Squaraines and Their Use as Near-Infrared Fluorescent Sensors for Protein[J]. J Phys Chem B, 2010,114(25):8574-8580. doi: 10.1021/jp1029536
Wang D C, Fan J L, Gao X Q. Carboxyl BODIPY Dyes from Bicarboxylic Anhydrides:One-Pot Preparation, Spectral Properties, Photostability, and Biolabeling[J]. J Org Chem, 2009,74(20):7675-7683. doi: 10.1021/jo901149y
Konermann L. Protein Unfolding and Denaturants. In Encyclopedia of Life Sciences[M]. Chichester:John Wiley & Sons Ltd, 2007.
Xu Y Q, Malkovskiy A, Pang Y. A Graphene Binding-Promoted Fluorescence Enhancement for Bovine Serum Albumin Recognition[J]. Chem Commun, 2011,47(23):6662-6664. doi: 10.1039/c1cc11355k
Stankovich S, Dikin D A, Piner R D. Synthesis of Graphene-Based Nanosheets via Chemical Reduction of Exfoliated Graphite Oxide[J]. Carbon, 2007,45(7):1558-1565. doi: 10.1016/j.carbon.2007.02.034
Paredes J I, Villar-Rodil S, Martiínez-Alonso A. Graphene Oxide Dispersions in Organic Solvents[J]. Langmuir, 2008,24(19):10560-10564. doi: 10.1021/la801744a
Xu Y Q, Liu Q, Li X P. A Zwitterionic Squaraine Dye with a Large Stokes Shift for in vivo and Site-Selective Protein Sensing[J]. Chem Commun, 2012,48(92):11313-11315. doi: 10.1039/c2cc36285f
Jisha V S, Arun K T, Hariharan M. Site-selective Binding and Dual Mode Recognition of Serum Albumin by a Squaraine Dye[J]. J Am Chem Soc, 2006,128(18):6024-6025. doi: 10.1021/ja061301x
Zhang S G. Fabrication of Novel Biomaterials Through Molecular Self-Assembly[J]. Nat Biotechnol, 2003,21(10)1171. doi: 10.1038/nbt874
Astruc D, Boisselier E, Ornelas C. Dendrimers Designed for Functions:From Physical, Photophysical, and Supramolecular Properties to Applications in Sensing, Catalysis, Molecular Electronics, Photonics, and Nanomedicine[J]. Chem Rev, 2010,110(4):1857-1959. doi: 10.1021/cr900327d
Molla M R, Prasad P, Thayumanavan S. Protein-induced Supramolecular Disassembly of Amphiphilic Polypeptide Nanoassemblies[J]. J Am Chem Soc, 2015,137(23):7286-7289. doi: 10.1021/jacs.5b04285
Zhang Y W, Yue X L, Kim B. Bovine Serum Albumin Nanoparticles with Fluorogenic Near-IR-emitting Squaraine Dyes[J]. ACS Appl Mater Interfaces, 2013,5(17):8710-8717. doi: 10.1021/am402361w
Wang H, Zhuang J M, Raghupathi K R. A Supramolecular Dissociation Strategy for Protein Sensing[J]. Chem Commun, 2015,51(97):17265-17268. doi: 10.1039/C5CC07408H
Fan X P, He Q Y, Sun S G. Nanoparticles Self-Assembled from Multiple Interactions:A Novel Near-Infrared Fluorescent Sensor for the Detection of Serum Albumin in Human Sera and Turn-On Live-Cell Imaging[J]. Chem Commun, 2016,52(6):1178-1181. doi: 10.1039/C5CC08154H
Grandini P, Mancin F, Tecilla P. Exploiting the Self-Assembly Strategy for the Design of Selective CuⅡ Ion Chemosensors[J]. Angew Chem Int Ed, 1999,38(20):3061-3064. doi: 10.1002/(ISSN)1521-3773
Mancin F, Scrimin P, Tecilla P. Amphiphilic Metalloaggregates:Catalysis, Transport, and Sensing[J]. Coord Chem Rev, 2009,253(17):2150-2165.
Pallavicini P, Diaz-Fernandez Y A, Pasotti L. Micelles as Nanosized Containers for the Self-assembly of Multicomponent Fluorescent Sensors[J]. Coord Chem Rev, 2009,253(17):2226-2240.
Azagarsamy M A, Yesilyurt V, Thayumanavan S. Disassembly of Dendritic Micellar Containers due to Protein Binding[J]. J Am Chem Soc, 2010,132(13):4550-4551. doi: 10.1021/ja100746d
Ryu J H, Roy R, Ventura J. Redox-Sensitive Disassembly of Amphiphilic Copolymer Based Micelles[J]. Langmuir, 2010,26(10):7086-7092. doi: 10.1021/la904437u
González D C, Savariar E N, Thayumanavan S. Fluorescence Patterns from Supramolecular Polymer Assembly and Disassembly for Sensing Metallo-and Nonmetalloproteins[J]. J Am Chem Soc, 2009,131(22):7708-7716. doi: 10.1021/ja900579g
Savariar E N, Ghosh S, Thayumanavan S. Disassembly of Noncovalent Amphiphilic Polymers with Proteins and Utility in Pattern Sensing[J]. J Am Chem Soc, 2008,130(16):5416-5417. doi: 10.1021/ja800164z
Sandanaraj B S, Demont R, Thayumanavan S. Generating Patterns for Sensing Using a Single Receptor Scaffold[J]. J Am Chem Soc, 2007,129(12):3506-3507. doi: 10.1021/ja070229f
Nakahara Y, Kida T, Nakatsuji Y. A Novel Fluorescent Indicator for Ba2+ in Aqueous Micellar Solutions[J]. Chem Commun, 2004(2):224-225. doi: 10.1039/b311613a
Morikawa M, Yoshihara M, Endo T. ATP as Building Blocks for the Self-Assembly of Excitonic Nanowires[J]. J Am Chem Soc, 2005,127(5):1358-1359. doi: 10.1021/ja043844h
Xu Y Q, Malkovskiy A, Wang Q M. Molecular Assembly of a Squaraine Dye with Cationic Surfactant and Nucleotides:Its Impact on Aggregation and Fluorescence Response[J]. Org Biomol Chem, 2011,9(8):2878-2884. doi: 10.1039/c0ob01061h
Bush K T, Keller S H, Nigam S K. Genesis and Reversal of the Ischemic Phenotype in Epithelial Cells[J]. J Clin Invest, 2000,106(5):621-626. doi: 10.1172/JCI10968
Di Monte D A, Lavasani M, Manning-Bog A B. Environmental Factors in Parkinson's Disease[J]. Neurotoxicology, 2002,23(4):487-502.
Feng R Z, Shi W N, Wang D J. Hierarchical Self-Assembly of Squaraine and Silica Nanoparticle Functionalized with Cationic Coordination Sites for Near Infrared Detection of ATP[J]. Sci Rep, 2017,7.
Xu Y Q, Li B H, Han P. Near-Infrared Fluorescent Detection of Glutathione via Reaction-Promoted Assembly of Squaraine-Analyte Adducts[J]. Analyst, 2013,138(4):1004-1007. doi: 10.1039/c2an36475a
He Q Y, Fan X P, Sun S G. Highly Selective Turn-On Detection of (strept) Avidin Based on Self-Assembled Near-Infrared Fluorescent Probes[J]. RSC Adv, 2015,5(48):38571-38576. doi: 10.1039/C5RA07185B
Xu Y Q, Li B H, Xiao L L. A Colorimetric and Near-Infrared Fluorescent Probe with High Sensitivity and Selectivity for Acid Phosphatase and Inhibitor Screening[J]. Chem Commun, 2014,50(63):8677-8680. doi: 10.1039/C3CC49254K
Zhou Q, Swager T M. Method for Enhancing the Sensitivity of Fluorescent Chemosensors:Energy Migration in Conjugated Polymers[J]. J Am Chem Soc, 1995,117(26):7017-7018. doi: 10.1021/ja00131a031
Tu J, Xiao L L, Jiang Y F. Near-Infrared Fluorescent Turn-On Detection of Paraquat Using an Assembly of Squaraine and Surfactants[J]. Sens Actuators B-Chem, 2015,215:382-387. doi: 10.1016/j.snb.2015.04.015
Tu J, Sun S G, Xu Y Q. A Novel Self-Assembled Platform for the Ratiometric Fluorescence Detection of Spermine[J]. Chem Commun, 2016,52(5):1040-1043. doi: 10.1039/C5CC07861J
Feng R Z, Xu Y Q, Zhao H W. A Novel Platform Self-Assembled from Squaraine-Embedded Zn(Ⅱ) Complexes for Selective Monitoring of ATP and Its Level Fluctuation in Mitotic Cells[J]. Analyst, 2016,141(11):3219-3223. doi: 10.1039/C6AN00646A
Xu Y Q, Li B H, Xiao L L. The Sphere-To-Rod Transition of Squaraine-Embedded Micelles:A Self-Assembly Platform Displays a Distinct Response to Cysteine and Homocysteine[J]. Chem Commun, 2013,49(70):7732-7734. doi: 10.1039/c3cc43223h
Xu Y Q, Li B H, Li W W. "ICT-not-quenching" Near Infrared Ratiometric Fluorescent Detection of Picric Acid in Aqueous Media[J]. Chem Commun, 2013,49(42):4764-4766. doi: 10.1039/c3cc41994k
Xu Y Q, Zhang D, Li B H. A Near Infrared Fluorescent Dye for Trivalent Ions Sensing and Working as a Molecular Keypad Lock[J]. RSC Adv, 2014,4(23):11634-11639. doi: 10.1039/c3ra47635a
Fan X P, Zhang D, Li H J. A BSA-Squaraine Hybrid System for Selectively Detecting Ag+ in Absolute PBS and Sequential Construction of Logic Functions[J]. Sensor Actuators B-Chem, 2017,245:290-296. doi: 10.1016/j.snb.2017.01.122
Jinghan ZHANG , Guanying CHEN . Progress in the application of rare-earth-doped upconversion nanoprobes in biological detection. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2335-2355. doi: 10.11862/CJIC.20240249
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
Han ZHANG , Jianfeng SUN , Jinsheng LIANG . Hydrothermal synthesis and luminescent properties of broadband near-infrared Na3CrF6 phosphor. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 349-356. doi: 10.11862/CJIC.20240098
Qi Wang , Yicong Gao , Feng Lu , Quli Fan . Preparation and Performance Characterization of the Second Near-Infrared Phototheranostic Probe: A New Design and Teaching Practice of Polymer Chemistry Comprehensive Experiment. University Chemistry, 2024, 39(11): 342-349. doi: 10.12461/PKU.DXHX202404141
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
Xiaowei TANG , Shiquan XIAO , Jingwen SUN , Yu ZHU , Xiaoting CHEN , Haiyan ZHANG . A zinc complex for the detection of anthrax biomarker. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1850-1860. doi: 10.11862/CJIC.20240173
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
Jiahui CHEN , Tingting ZHENG , Xiuyun ZHANG , Wei LÜ . Research progress of near-infrared absorption inorganic nanomaterials in photothermal and photodynamic therapy of tumors. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2396-2414. doi: 10.11862/CJIC.20240106
Xinyi Hong , Tailing Xue , Zhou Xu , Enrong Xie , Mingkai Wu , Qingqing Wang , Lina Wu . Non-Site-Specific Fluorescent Labeling of Proteins as a Chemical Biology Experiment. University Chemistry, 2024, 39(4): 351-360. doi: 10.3866/PKU.DXHX202310010
Qin Hou , Jiayi Hou , Aiju Shi , Xingliang Xu , Yuanhong Zhang , Yijing Li , Juying Hou , Yanfang Wang . Preparation of Cuprous Iodide Coordination Polymer and Fluorescent Detection of Nitrite: A Comprehensive Chemical Design Experiment. University Chemistry, 2024, 39(8): 221-229. doi: 10.3866/PKU.DXHX202312056
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
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
Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb2+ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
Xinyu ZENG , Guhua TANG , Jianming OUYANG . Inhibitory effect of Desmodium styracifolium polysaccharides with different content of carboxyl groups on the growth, aggregation and cell adhesion of calcium oxalate crystals. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1563-1576. doi: 10.11862/CJIC.20230374
Yanyang Li , Zongpei Zhang , Kai Li , Shuangquan Zang . Ideological and Political Design for the Comprehensive Experiment of the Synthesis and Aggregation-Induced Emission (AIE) Performance Study of Salicylaldehyde Schiff-Base. University Chemistry, 2024, 39(2): 105-109. doi: 10.3866/PKU.DXHX202307020
Di Yang , Jiayi Wei , Hong Zhai , Xin Wang , Taiming Sun , Haole Song , Haiyan Wang . Rapid Detection of SARS-CoV-2 Using an Innovative “Magic Strip”. University Chemistry, 2024, 39(4): 373-381. doi: 10.3866/PKU.DXHX202312023
. . Chinese Journal of Inorganic Chemistry, 2024, 40(12): 0-0.
Qilong Fang , Yiqi Li , Jiangyihui Sheng , Quan Yuan , Jie Tan . Magical Pesticide Residue Detection Test Strips: Aptamer-based Lateral Flow Test Strips for Organophosphorus Pesticide Detection. University Chemistry, 2024, 39(5): 80-89. doi: 10.3866/PKU.DXHX202310004
Hong LI , Xiaoying DING , Cihang LIU , Jinghan ZHANG , Yanying RAO . Detection of iron and copper ions based on gold nanorod etching colorimetry. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 953-962. doi: 10.11862/CJIC.20230370
Yang YANG , Pengcheng LI , Zhan SHU , Nengrong TU , Zonghua WANG . Plasmon-enhanced upconversion luminescence and application of molecular detection. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 877-884. doi: 10.11862/CJIC.20230440