Advanced in Fluorescent Probes Based on Excited State Intramolecular Proton Transfer
- Corresponding author: XU Yongqian, xuyq@nwsuaf.edu.cn
Citation:
WANG Dejia, XU Yongqian, SUN Shiguo, LI Hongjuan. Advanced in Fluorescent Probes Based on Excited State Intramolecular Proton Transfer[J]. Chinese Journal of Applied Chemistry,
;2018, 35(1): 1-20.
doi:
10.11944/j.issn.1000-0518.2018.01.170328
Lee M H, Kim J S, Sessler J L. Small Molecule-based Ratiometric Fluorescence Probes for Cations, Anions, and Biomolecules[J]. Chem Soc Rev, 2015,44(13):4185-4191. doi: 10.1039/C4CS00280F
Berezin M Y, Achilefu S. Fluorescence Lifetime Measurements and Biological Imaging[J]. Chem Rev, 2010,110(5):2641-2684. doi: 10.1021/cr900343z
Wu J S, Liu W M, Ge J C. New Sensing Mechanisms for Design of Fluorescent Chemosensors Emerging in Recent Years[J]. Chem Soc Rev, 2011,40(7):3483-3495. doi: 10.1039/c0cs00224k
Kwon J E, Park S Y. Advanced Organic Optoelectronic Materials:Harnessing Excited-State Intramolecular Proton Transfer(ESIPT) Process[J]. Adv Mater, 2011,23(32):3615-3642. doi: 10.1002/adma.v23.32
Hsieh C C, Jiang C M, Chou P T. Recent Experimental Advances on Excited-State Intramolecular Proton Coupled Electron Transfer Reaction[J]. Acc Chem Res, 2010,43(10):1364-1374. doi: 10.1021/ar1000499
Tang K C, Chang M J, Lin T Y. Fine Tuning the Energetics of Excited-State Intramolecular Proton Transfer(ESIPT):White Light Generation in a Single ESIPT System[J]. J Am Chem Soc, 2011,133(44):17738-17745. doi: 10.1021/ja2062693
Luxami V, Kumar S. Molecular Half-subtractor Based on 3, 3'-Bis(1H-benzimidazolyl-2-yl)[1, 1']binaphthalenyl-2, 2'-diol[J]. New J Chem, 2008,32(12):2074-2079. doi: 10.1039/b805558k
HU Rui, GUO Xudong, YANG Guoqiang. Investigation on the Property of the ESIPT Compounds and Its Application as Fluorescence Chemical Sensor[J]. Imag Sci Photochem, 2013,31(5):335-348. doi: 10.7517/j.issn.1674-0475.2013.05.335
Wang J F, Li Y B, Patel N G. A Single Molecular Probe for Multi-analyte(Cr3+, Al3+ and Fe3+) Detection in Aqueous Medium and Its Biological Application[J]. Chem Commun, 2014,50(82):12258-12261. doi: 10.1039/C4CC04731A
Chu Q H, Medvetz D A, Pang Y. A Polymeric Colorimetric Sensor with Excited-State Intramolecular Proton Transfer for Anionic Species[J]. Chem Mater, 2007,19(26):6421-6429. doi: 10.1021/cm0713982
Ma J, Zhao J Z, Yang P. New Excited State Intramolecular Proton Transfer(ESIPT) Dyes Based on Naphthalimide and Observation of Long-lived Triplet Excited States[J]. Chem Commun, 2012,48(78):9720-9722. doi: 10.1039/c2cc35210a
Yang P, Zhao J Z, Wu W H. Accessing the Long-lived Triplet Excited States in Bodipy-conjugated 2-(2-Hydroxyphenyl) Benzothiazole/Benzoxazoles and Applications as Organic Triplet Photosensitizers for Photooxidations[J]. J Org Chem, 2012,77(14):6166-6178. doi: 10.1021/jo300943t
Kim T I, Kang H J, Han G. A Highly Selective Fluorescent ESIPT Probe for the Dual Specificity Phosphatase MKP-6[J]. Chem Commun, 2009,39:5895-5897.
Hu R, Feng J, Hu D H. A Rapid Aqueous Fluoride Ion Sensor with Dual Output Modes[J]. Angew Chem Int Ed, 2010,49(29):4915-4918. doi: 10.1002/anie.v49:29
Li X, Tao R R, Hong L J. Visualizing Peroxynitrite Fluxes in Endothelial Cells Reveals the Dynamic Progression of Brain Vascular Injury[J]. J Am Chem Soc, 2015,137(38):12296-12303. doi: 10.1021/jacs.5b06865
Sinha S, Chowdhury B, Ghosh P. A Highly Sensitive ESIPT-based Ratiometric Fluorescence Sensor for Selective Detection of Al3+[J]. Inorg Chem, 2016,55(18):9212-9220. doi: 10.1021/acs.inorgchem.6b01170
Tang L J, Shi J Z, Huang Z L. An ESIPT-based Fluorescent Probe for Selective Detection of Homocysteine and Its Application in Live-Cell Imaging[J]. Tetrahedron Lett, 2016,57(47):5227-5231. doi: 10.1016/j.tetlet.2016.10.034
Klymchenko A S, Shvadchak V V, Yushchenko D A. Excited-State Intramolecular Proton Transfer Distinguishes Microenvironments in Singleand Double-stranded DNA[J]. J Phys Chem B, 2008,112(38):12050-12055. doi: 10.1021/jp8058068
Dziuba D, Postupalenko V Y, Spadafora M. A Universal Nucleoside with Strong Two-band Switchable Fluorescence and Sensitivity to the Environment for Investigating DNA Interactions[J]. J Am Chem Soc, 2012,134(24):10209-10213. doi: 10.1021/ja3030388
Kenfack C A, Klymchenko A S, Duportail G. Ab Initio Study of the Solvent H-Bonding Effect on ESIPT Reaction and Electronic Transitions of 3-Hydroxychromone Derivatives[J]. Phys Chem Chem Phys, 2012,14(25):8910-8918. doi: 10.1039/c2cp40869d
Paul B K, Guchhait N. 1-Hydroxy-2-naphthaldehyde:A Prospective Excited-State Intramolecular Proton Transfer(ESIPT) Probe with Multi-faceted Applications[J]. J Lumin, 2012,132(8):2194-2208. doi: 10.1016/j.jlumin.2012.03.036
Hadjoudis E, Mavridis I M. Photochromism and Thermochromism of Schiff Bases in the Solid State:Structural Aspects[J]. Chem Soc Rev, 2004,33(9):579-88.
Han D Y, Kim J M, Kim J H. ESIPT-based Anthraquinonylcalix[4] crown Chemosensor for In3+[J]. Tetrahedron Lett, 2010,51(15):1947-1951. doi: 10.1016/j.tetlet.2010.02.006
Schmidtke S J, Underwood D F, Blank D A. Following the Solvent Directly During Ultrafast Excited State Proton Transfer[J]. J Am Chem Soc, 2004,126(28):8620-8621. doi: 10.1021/ja048639g
Chien T C, Dias L G, Arantes G M. 1-(2-Quinolyl)-2-naphthol:A New Intra-Intermolecular Photoacid Photobase Molecule[J]. J Photochem Photobiol A, 2008,194(1):37-48. doi: 10.1016/j.jphotochem.2007.07.012
SakaiK I, Takahashi S, Kobayashi A. Excited State Intramolecular Proton Transfer(ESIPT) in Six-coordinated Zinc(Ⅱ)-Quinoxaline Complexes with Ligand Hydrogen Bonds:Their Fluorescent Properties Sensitive to Axial Positions[J]. Dalton Trans, 2010,39(8):1989-1995. doi: 10.1039/b919613g
ZHANG Peng, ZHANG Youming, LIN Qi. Principle and the Research Progress of Fluorescent Chemosensors for Cations Recognition[J]. Chinese J Org Chem, 2014,37(7):1300-1321.
Gao M, Yu F B, Lv C J. Fluorescent Chemical Probes for Accurate Tumor Diagnosis and Targeting Therapy[J]. Chem Soc Rev, 2017,46(8):2237-2271. doi: 10.1039/C6CS00908E
Sinkeldam R W, Greco N J, Tor Y. Fluorescent Analogs of Biomolecular Building Blocks:Design, Properties, and Applications[J]. Chem Rev, 2010,110(5):2579-2619. doi: 10.1021/cr900301e
Xu, PangY. Zn2+-Triggered Excited-State Intramolecular Proton Transfer:A Sensitive Probe with Near-infrared Emission from Bis(benzoxazole) Derivative[J]. Dalton Trans, 2011,40(7):1503-1509. doi: 10.1039/c0dt01376e
Huang L Y, Gu B, Su W. Proton Donor Modulating ESIPT-based Fluorescent Probes for Highly Sensitive and Selective Detection of Cu2+[J]. RSC Adv, 2015,5(93):76296-76301. doi: 10.1039/C5RA14443D
Chen X Q, Pradhan T H, Wang F. Fluorescent Chemosensors Based on Spiroring-opening of Xanthenes and Related Derivatives[J]. Chem Rev, 2012,112(3):1910-1956. doi: 10.1021/cr200201z
Xu Y Q, Xiao L L, Zhang Y F. Substituent Effect on Fluorophores Instead of Ionophores:Its Implication in Highly Selective Fluorescent Probes for Zn2+ over Cd2+[J]. RSC Adv, 2014,4(10):4827-4830. doi: 10.1039/c3ra46468g
Xu Y Q, Xiao L L, Sun S G. Switchable and Selective Detection of Zn2+ or Cd2+ in Living Cells Based on 3'-O-substituted Arrangement of Benzoxazole-derived Fluorescent Probes[J]. Chem Commun, 2014,50(56):7514-7516. doi: 10.1039/C4CC02335H
Gale P A, Caltagirone C. Anion Sensing by Small Molecules and Molecular Ensembles[J]. Chem Soc Rev, 2015,44(13):4212-4227. doi: 10.1039/C4CS00179F
Ashton T D, Jolliffe K A, Pfeffer F M. Luminescent Probes for the Bioimaging of Small Anionic Species in Vitro and in Vivo[J]. Chem Soc Rev, 2015,44(14):4547-4595. doi: 10.1039/C4CS00372A
Wu Y K, Peng X J, Fan J L. Fluorescence Sensing of Anions Based on Inhibition of Excited-State Intramolecular Proton Transfer[J]. J Org Chem, 2007,72(1):62-70. doi: 10.1021/jo061634c
Goswami S, Manna A, Paul S. Resonance-assisted Hydrogen Bonding Induced Nucleophilic Addition to Hamper ESIPT:Ratiometric Detection of Cyanide in Aqueous Media[J]. Chem Commun, 2013,49(28):2912-2914. doi: 10.1039/c3cc39256b
Porel M, Ramalingam V, Domaradzki M E. Chloride Sensing via Suppression of Excited State Intramolecular Proton Transfer in Squaramides[J]. Chem Commun, 2013,49(16):1633-1635. doi: 10.1039/c3cc38767d
Chen W H, Xing Y, Pang Y. A Highly Selective Pyrophosphate Sensor Based on ESIPT Turn-on in Water[J]. Org Lett, 2011,13(6):1362-1365. doi: 10.1021/ol200054w
Sedgwick A C, Sun X L, Kim G. Boronate Based Fluorescence(ESIPT) Probe for Peroxynitrite[J]. Chem Commun, 2016,52(83):12350-12352. doi: 10.1039/C6CC06829D
Pan Y M, Huang J, Han Y F. A New ESIPT-based Fluorescent Probe for Highly Selective and Sensitive Detection of HClO in Aqueous Solution[J]. Tetrahedron Lett, 2017,58(13):1301-1304. doi: 10.1016/j.tetlet.2017.02.043
Xiao L L, Sun S G, Pei Z C. A Ga3+ Self-assembled Fluorescent Probe for ATP Imaging in Vivo[J]. Biosens Bioelectron, 2015,65:166-170. doi: 10.1016/j.bios.2014.10.038
Chen X Q, Zhou Y, Peng X J. Fluorescent and Colorimetric Probes for Detection of Thiols[J]. Chem Soc Rev, 2010,39(6):2120-2135. doi: 10.1039/b925092a
Fernandez A, Vendrell M. Smart Fluorescent Probes for Imaging Macrophage Activity[J]. Chem Soc Rev, 2016,45(5):1182-1196. doi: 10.1039/C5CS00567A
Xiao L L, Tu J, Sun S G. A Fluorescent Probe for Hydrazine and Its in Vivo Applications[J]. RSC Adv, 2014,4(79):41807-41811. doi: 10.1039/C4RA08101C
Chen Z, Zhong X X, Qu W B. A Highly Selective HBT-based "Turn-On" Fluorescent Probe for Hydrazine Detection and Its Application[J]. Tetrahedron Lett, 2017,58(26):2596-2601. doi: 10.1016/j.tetlet.2017.05.071
Zhang D, Yang Z H, Li H J. A Simple Excited-State Intramolecular Proton Transfer Probe Based on a New Strategy of Thiol-azide Reaction for the Selective Sensing of Cysteine and Glutathione[J]. Chem Commun, 2016,52(4):749-752. doi: 10.1039/C5CC07298K
Goswami S, Manna A, Paul S. A Turn On ESIPT Probe for Rapid and Ratiometric Fluorogenic Detection of Homocysteine and Cysteine in Water with Live Cell-Imaging[J]. Tetrahedron Lett, 2014,55(2):490-494. doi: 10.1016/j.tetlet.2013.11.055
Liu X J, Tian H H, Yang L. A Sensitive and Selective Fluorescent Probe for the Detection of Hydrogen Peroxide with a Red Emission and a Large Stokes Shift[J]. Sens Actuators B, 2018,255:1160-1165. doi: 10.1016/j.snb.2017.05.151
Li G P, Zhu D J, Liu Q. Rapid Detection of Hydrogen Peroxide Based on Aggregation Induced Ratiometric Fluorescence Change[J]. Org Lett, 2013,15(4):924-927. doi: 10.1021/ol4000845
Wang L Q, Zang Q G, Chen W S. A Ratiometric Fluorescent Probe with Excited-State Intramolecular Proton Transfer for Benzoyl Peroxide[J]. RSC Adv, 2013,3(23):8674-8676. doi: 10.1039/c3ra41209a
Deng B B, Ren M G, Kong X Q. An ESIPT Based Fluorescent Probe for Imaging Hydrogen Sulfide with a Large Turn-On Fluorescence Signal[J]. RSC Adv, 2016,6(67):62406-62410. doi: 10.1039/C6RA12127F
Chen L Y, Wu D, Lim C S. A Two-photon Fluorescent Probe for Specific Detection of Hydrogen Sulfide Based on a Familiar ESIPT Fluorophore Bearing AIE Characteristics[J]. Chem Commun, 2017,53(35):4791-4794. doi: 10.1039/C7CC01695F
Yushchenko D A, Fauerbach J A, Thirunavukkuarasu S. Fluorescent Ratiometric MFC Probe Sensitive to Early Stages of α-Synuclein Aggregation[J]. J Am Chem Soc, 2010,132(23):7860-7861. doi: 10.1021/ja102838n
Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
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
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
Zhenhua Wang , Haoyang Feng , Xiaoyang Shao , Wenru Fan . Vitamins in Solid Propellants: Controlled Synthesis of Neutral Macromolecular Bonding Agents. University Chemistry, 2025, 40(4): 1-9. doi: 10.3866/PKU.DXHX202401007
Yu SU , Xinlian FAN , Yao YIN , Lin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126
Shanghua Li , Malin Li , Xiwen Chi , Xin Yin , Zhaodi Luo , Jihong Yu . 基于高离子迁移动力学的取向ZnQ分子筛保护层实现高稳定水系锌金属负极的构筑. Acta Physico-Chimica Sinica, 2025, 41(1): 2309003-. doi: 10.3866/PKU.WHXB202309003
Yuyao Wang , Zhitao Cao , Zeyu Du , Xinxin Cao , Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-. doi: 10.3866/PKU.WHXB202406014
Wenyan Dan , Weijie Li , Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060
Zhifang SU , Zongjie GUAN , Yu FANG . Process of electrocatalytic synthesis of small molecule substances by porous framework materials. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2373-2395. doi: 10.11862/CJIC.20240290
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
Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al2O3催化剂光热催化CO2甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
Zheqi Wang , Yawen Lin , Shunliu Deng , Huijun Zhang , Jinmei Zhou . Antiviral Strategies: A Brief Review of the Development History of Small Molecule Antiviral Drugs. University Chemistry, 2024, 39(9): 85-93. doi: 10.12461/PKU.DXHX202403108
Qiaojia GUO , Junkai CAI , Chunying DUAN . Effects of anions on the structural regulation of Zn-salen-modified metal-organic cage. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2203-2211. doi: 10.11862/CJIC.20240209
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
Yifeng Xu , Jiquan Liu , Bin Cui , Yan Li , Gang Xie , Ying Yang . “Xiao Li’s School Adventures: The Working Principles and Safety Risks of Lithium-ion Batteries”. University Chemistry, 2024, 39(9): 259-265. doi: 10.12461/PKU.DXHX202404009
Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu2+. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe3+ and Cu2+ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
Jiaxun Wu , Mingde Li , Li Dang . The R eaction of Metal Selenium Complexes with Olefins as a Tutorial Case Study for Analyzing Molecular Orbital Interaction Modes. University Chemistry, 2025, 40(3): 108-115. doi: 10.12461/PKU.DXHX202405098
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