Abstract
Fluorescent chemosensors are highly valuable in a variety of fields including environmental chemistry, analytical chemistry and biomedical science. They have provided accurate, online and low-cost detection of toxic heavy metal ions, anions and enzymes with high selectivity and sensitivity. Coumarins, with the structure of benzopyrone, have many advantages including high fluorescence quantum yield, large Stokes shift, excellent light stability and less toxicity. By far coumarin has been used as fluorescent probes of pH, for detection of nitric oxide, nitroxide and hydrogen peroxide. Moreover, coumarin derivatives have served as good chemosensors of anions including cyanide, fluoride, pyrophosphate, acetate, benzoate and dihydrogenphosphate as well as various metal ions comprised of Hg(II), Cu(II), Zn(II), Ni(II), Ca(II), Pb(II), Mg(II), Fe(III), Al(III), Cr(III) and Ag(I). Several systems containing coumarin exhibited simultaneous sensitivity toward two or more different metal ions, e.g., Ca(II) and Mg(II), Ni(II) and Co(II), Cu(II) and Hg(II), Na(I) and K(I), Cu(II) and Ni(II), Hg(II) and Ag(I), Cu(II)/Ni(II)/Cd(II), Zn(II)/Cd(II)/Pb(II) or Ni(II)/Pd(II)/Ag(I). The sensing approach toward the ion has been discussed in detail along their detection limit to find the efficacy of the probe easier. Recently, scientists have been working on synthesizing novel fluorescence chemosensors with multiple-ion recognition ability to make the fluorescence sensing more effective and prolific.
Similar content being viewed by others
Availability of data and material
All the written material is new not a copy.
Code availability
No.
References
Ahmadi S, Dabbagh HA, Grieco P, Balalaie S (2020) A cystine-based dual chemosensor for fluorescent-colorimetric detection of CN(-) and fluorescent detection of Fe(3+) in aqueous media: synthesis, spectroscopic, and DFT studies. Spectrochim Acta Part-A Mol Biomol Spectrosc 228:117696
Ali R, Dwivedi SK, Mishra H, Misra A (2020) Imidazole-coumarin containing D-A type fluorescent probe: synthesis photophysical properties and sensing behavior for F− and CN− anion. Dyes Pigments 175:108163
An R, Hou Z, Li J-T, Yu H-N, Mou Y-H, Guo C (2018) Design, synthesis and biological evaluation of novel 4-substituted coumarin derivatives as antitumor agents. Molecules 23(9):2281
Anamika, Divya U, Ekta NJ, Shivali S (2018) Advances in synthesis and potentially bioactive of coumarin derivatives. Curr Org Chem 22(26):2509–2536
Aron AT, Ramos-Torres KM, Cotruvo JA Jr, Chang CJ (2015) Recognition-and reactivity-based fluorescent probes for studying transition metal signaling in living systems. Acc Chem Res 48(8):2434–2442
Aydıner B (2019) A chemodosimeter approach for selective colorimetric and fluorimetric cyanide detection using coumarin based fluorescent dyes. J Photochem Photobiol A Chem 382:111916
Branca JJV, Morucci G, Becatti M, Carrino D, Ghelardini C, Gulisano M, Di Cesare Mannelli L, Pacini A (2019) Cannabidiol protects dopaminergic neuronal cells from cadmium. Int J Environ Res Public Health 16(22):4420
Cao Z, Fan X, Yang Z, Zhang X, Ding N, Ding Y, Zhang W (2020) Solvent directed discrimination of metal ions using a coumarin-pyridine fluorescence receptor. Sens Actuators B Chem 310:127855
Chao SH, Suzuki Y, Zysk JR, Cheung WY (1984) Activation of calmodulin by various metal cations as a function of ionic radius. Mol Pharmacol 26(1):75–82
Chen H, Sun T, Qiao X-G, Tang Q-O, Zhao S-C, Zhou Z (2018) Red-emitting fluorescent probe for detecting hypochlorite acid in vitro and in vivo. Spectrochim Acta Part A Mol Biomol Spectrosc 204:196–202
Cheng S, Pan X, Shi M, Su T, Zhang C, Zhao W, Dong W (2020) A coumarin-connected carboxylic indolinium sensor for cyanide detection in absolute aqueous medium and its application in biological cell imaging. Spectrochim Acta Part A Mol Biomol Spectrosc 228:117710
Choong G, Liu Y, Templeton DM (2014) Interplay of calcium and cadmium in mediating cadmium toxicity. Chem Biol Interact 211:54–65
Danilewicz JC (2003) Review of reaction mechanisms of oxygen and proposed intermediate reduction products in wine: central role of iron and copper. Am J Enol Vitic 54(2):73–85
Darbre PD (2005) Aluminium, antiperspirants and breast cancer. J Inorg Biochem 99(9):1912–1919
Decottignies V, Filippi G, Bruchet A (2007) Characterisation of odour masking agents often used in the solid waste industry for odour abatement. Water Sci Technol 55(5):359–364
Dietrich O, Levin J, Ahmadi S-A, Plate A, Reiser MF, Bötzel K, Giese A, Ertl-Wagner B (2017) MR imaging differentiation of Fe2+ and Fe3+ based on relaxation and magnetic susceptibility properties. Neuroradiology 59(4):403–409
dos Santos Carlos F, da Silva LA, Zanlorenzi C, Nunes FS (2020) A novel macrocycle acridine-based fluorescent chemosensor for selective detection of Cd2+ in Brazilian sugarcane spirit and tobacco cigarette smoke extract. Inorgan Chim Acta 508:119634
Drexhage KH (1973) Structure and properties of laser dyes. In: Schäfer FP (ed) Dye lasers. Topics in applied physics, vol 1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-11579-4_4.
Ellis PD, Strang P, Potter JD (1984) Cadmium-substituted skeletal troponin C. Cadmium-113 NMR spectroscopy and metal binding investigations. J Biol Chem 259(16):10348–10356
Elmas SNK, Gunay IB, Koran K, Ozen F, Aydin D, Arslan FN, Gorgulu AO, Yilmaz I (2019) An ultrasensitive and selective ‘turn off’fluorescent sensor with simple operation for the determination of trace copper (II) ions in water and various beverage samples. Supramol Chem 31(12):756–766
Elmas SNK, Dincer ZE, Erturk AS, Bostanci A, Karagoz A, Koca M, Sadi G, Yilmaz I (2020) A novel fluorescent probe based on isocoumarin for Hg2+ and Fe3+ ions and its application in live-cell imaging. Spectrochim Acta Part A Mol Biomol Spectrosc 224:117402
Emami S, Dadashpour S (2015) Current developments of coumarin-based anti-cancer agents in medicinal chemistry. Eur J Med Chem 102:611–630
Ergun E, Ergun Ü, İleri Ö, Küçükmüzevir MF (2018) An investigation of some Schiff base derivatives as chemosensors for Zn (II): the performance characteristics and potential applications. Spectrochim Acta Part A Mol Biomol Spectrosc 203:273–286
Fasco MJ, Hildebrandt EF, Suttie JW (1982) Evidence that warfarin anticoagulant action involves two distinct reductase activities. J Biol Chem 257(19):11210–11212
Fazio T, Warner CR (1990) A review of sulphites in foods: analytical methodology and reported findings. Food Addit Contam 7(4):433–454
Flatman RH, Eustaquio A, Li S-M, Heide L, Maxwell A (2006) Structure-activity relationships of aminocoumarin-type gyrase and topoisomerase IV inhibitors obtained by combinatorial biosynthesis. Antimicrob Agents Chemother 50(4):1136–1142
Francois F, Frederic M, Jean-Roger D, Arielle G, Florence B, Betsy C (2002) Coumarin in plants and fruits: implication in perfumery. Perfumer Flavorist 27(2):32–36
Gandioso A, Bresolí-Obach R, Nin-Hill A, Bosch M, Palau M, Galindo A, Contreras S, Rovira A, Rovira C, Nonell S, Marchan V (2018) Redesigning the coumarin scaffold into small bright fluorophores with far-red to near-infrared emission and large Stokes shifts useful for cell imaging. J Org Chem 83(3):1185–1195
Gong D, Tian Y, Yang C, Iqbal A, Wang Z, Liu W, Qin W, Zhu X, Guo H (2016) A fluorescence enhancement probe based on BODIPY for the discrimination of cysteine from homocysteine and glutathione. Biosens Bioelectron 85:178–183
Goswami S, Paul S, Manna A (2013) Selective “naked eye” detection of Al (III) and PPi in aqueous media on a rhodamine–isatin hybrid moiety. RSC Adv 3(27):10639–10643
Gu L, Zheng T, Xu Z, Song Y, Li H, Xia S, Shen L (2019) A novel bifunctional fluorescent and colorimetric probe for detection of mercury and fluoride ions. Spectrochim Acta Part A Mol Biomol Spectrosc 207:88–95
Guha S, Lohar S, Sahana A, Banerjee A, Safin DA, Babashkina MG, Mitoraj MP, Bolte M, Garcia Y, Mukhopadhyay SK, Das D (2013) A coumarin-based “turn-on” fluorescent sensor for the determination of Al3+: single crystal X-ray structure and cell staining properties. Dalton Trans 42(28):10198–10207
Gupta G, Sharma G, Koch B, Park S, Lee SS, Kim J (2013) Syntheses, characterization and molecular structures of novel Ru (II), Rh (III) and Ir (III) complexes and their possible roles as antitumour and cytotoxic agents. New J Chem 37(8):2573–2581
Gupta AS, Paul K, Luxami V (2018) A new ‘Turn-on’PET-CHEF based fluorescent sensor for Al3+ and CN− ions: applications in real samples. Anal Methods 10(9):983–990
Hara K, Sato T, Katoh R, Furube A, Ohga Y, Shinpo A, Suga S, Sayama K, Sugihara H, Arakawa H (2003) Molecular design of coumarin dyes for efficient dye-sensitized solar cells. J Phys Chem B 107(2):597–606
Hargrove AE, Nieto S, Zhang T, Sessler JL, Anslyn EV (2011) Artificial receptors for the recognition of phosphorylated molecules. Chem Rev 111(11):6603–6782
Hassan MZ, Osman H, Ali MA, Ahsan MJ (2016) Therapeutic potential of coumarins as antiviral agents. Eur J Med Chem 123:236–255
He X, Xie Q, Fan J, Xu C, Xu W, Li Y, Ding F, Deng H, Chen H, Shen J (2020) Dual-functional chemosensor with colorimetric/ratiometric response to Cu (II)/Zn (II) ions and its applications in bioimaging and molecular logic gates. Dyes Pigments 177:108255
Hossain SM, Singh K, Lakma A, Pradhan RN, Singh AK (2017) A schiff base ligand of coumarin derivative as an ICT-Based fluorescence chemosensor for Al3+. Sens Actuators B Chem 239:1109–1117
Hu Y, Yin J, Yoon J (2016) A multi-responsive cyanine-based colorimetric chemosensor containing dipicolylamine moieties for the detection of Zn(II) and Cu(II) ions. Sens Actuat B Chem 230:40–45
Hu C, Li J, Yan L (2019) A fluorescent probe for hypochlorite with colorimetric and fluorometric characteristics and imaging in living cells. Anal Biochem 566:32–36
Hu JH, Yin ZY, Gui K, Fu QQ, Yao Y, Fu XM, Liu HX (2020) A novel supramolecular polymer gel-based long-alkyl-chain-functionalized coumarin acylhydrazone for the sequential detection and separation of toxic ions. Soft Matter 16(4):1029–1033
Hua Y, Wei Q, Wu G, Sun Z-B, Shang Y-J (2020) Fluorescent determination of calcium ion using a coumarinyl pyrazoline scaffold and its application in living cells. Anal Lett 53(6):960–972
Hudnall TW, Chiu C-W, Gabbaï FP (2009) Fluoride ion recognition by chelating and cationic boranes. Acc Chem Res 42(2):388–397
Isaac A, Davis J, Livingstone C, Wain AJ, Compton RG (2006) Electroanalytical methods for the determination of sulfite in food and beverages. TrAC Trends Anal Chem 25(6):589–598
Jacobson KB, Turner JE (1980) The interaction of cadmium and certain other metal ions with proteins and nucleic acids. Toxicology 16(1):1–37
Jameel E, Umar T, Kumar J, Hoda N (2016) Coumarin: a privileged scaffold for the design and development of antineurodegenerative agents. Chem Biol Drug Des 87(1):21–38
Jin L, Tan X, Dai L, Zhao C, Wang W, Wang Q (2019) A novel coumarin-based fluorescent probe with fine selectivity and sensitivity for hypochlorite and its application in cell imaging. Talanta 202:190–197
Jo J, Lee D (2009) Turn-on fluorescence detection of cyanide in water: activation of latent fluorophores through remote hydrogen bonds that mimic peptide β-turn motif. J Am Chem Soc 131(44):16283–16291
Johnson AD, Curtis RM, Wallace KJ (2019) Low molecular weight fluorescent probes (LMFPs) to detect the group 12 metal triad. Chemosensors 7(2):22
Jonaghani MZ, Zali-Boeini H, Moradi H (2019) A coumarin based highly sensitive fluorescent chemosensor for selective detection of zinc ion. Spectrochim Acta Part A Mol Biomol Spectrosc 207:16–22
Jones G, Jackson WR, Choi CY, Bergmark WR (1985) Solvent effects on emission yield and lifetime for coumarin laser dyes, requirements for a rotatory decay mechanism. J Phys Chem 89(2):294–300
Jung Y, Jung J, Huh Y, Kim D (2018) Benzo [] coumarin-based fluorescent probes for bioimaging applications. J Anal Methods Chem 2018:11. Article ID 5249765. https://doi.org/10.1155/2018/5249765
Kashyap KS, Hira SK, Dey S (2019) Photo-physical aspects of BODIPY-coumarin conjugated sensor and detection of Al3+ in MCF-7 cell. Supramol Chem 31(11):695–702
Kathiravan MK, Salake AB, Chothe AS, Dudhe PB, Watode RP, Mukta MS, Gadhwe S (2012) The biology and chemistry of antifungal agents: a review. Bioorg Med Chem 20(19):5678–5698
Kaya EN, Yuksel F, Özpınar GA, Bulut M, Durmuş M (2014) 7-Oxy-3-(3, 4, 5-trimethoxyphenyl) coumarin substituted phthalonitrile derivatives as fluorescent sensors for detection of Fe3+ ions: experimental and theoretical study. Sensors Actuators B Chem 194:377–388
Keawwangchai T, Morakot N, Wanno B (2013) Fluorescent sensors based on BODIPY derivatives for aluminium ion recognition: an experimental and theoretical study. J Mol Model 19(3):1435–1444
Kinga K, Anna E-P, Elzbieta B (2016) Sunscreening and photosensitizing properties of coumarins and their derivatives. Lett Drug Des Discov 13(5):465–474
Kontogiorgis CA, Hadjipavlou-Litina DJ (2005) Synthesis and antiinflammatory activity of coumarin derivatives. J Med Chem 48(20):6400–6408
Kubier A, Wilkin RT, Pichler T (2019) Cadmium in soils and groundwater: a review. Appl Geochem 108:104388
Kursunlu AN (2015) A fluorescent “turn on” chemosensor based on Bodipy–anthraquinone for Al (III) ions: synthesis and complexation/spectroscopic studies. RSC Adv 5(51):41025–41032
Kuyucak N, Akcil A (2013) Cyanide and removal options from effluents in gold mining and metallurgical processes. Miner Eng 50:13–29
Kwon HY, Liu X, Choi EG, Lee JY, Choi SY, Kim JY, Wang L, Park SJ, Kim B, Lee YA, Kim JJ, Kang NY, Chang YT (2019) Development of a universal fluorescent probe for gram-positive bacteria. Angew Chem Int Ed 58(25):8426–8431
Lai J, Moxey A, Nowak G, Vashum K, Bailey K, McEvoy M, (2000) J Affect Disord, 56, 189; (b) JH Weiss, SL Sensi and JY Koh. Trends Pharmacol Sci 21, 395
Laisalmi M, Kokki H, Soikkeli A, Markkanen H, Yli-Hankala A, Rosenberg P, Lindgren L (2006) Effects of cigarette smoking on serum fluoride concentrations and renal function integrity after 1 MAC-h sevoflurane anaesthesia. Acta Anaesthesiol Scand 50(8):982–987
Laitos JG (2012) Cyanide, mining, and the environment. Pace Environ Law Rev 30(3):869. https://digitalcommons.pace.edu/pelr/vol30/iss3/2
Langer GA, Nudd LM (1983) Effects of cations, phospholipases, and neuraminidase on calcium binding to"gas-dissected" membranes from cultured cardiac cells. Circ Res 53(4):482–490
Lee MH, Kim JS, Sessler JL (2015) Small molecule-based ratiometric fluorescence probes for cations, anions, and biomolecules. Chem Soc Rev 44(13):4185–4191
Li C-R, Li S-L, Yang Z-Y (2017) Development of a coumarin-furan conjugate as Zn2+ ratiometric fluorescent probe in ethanol-water system. Spectrochim Acta Part A Mol Biomol Spectrosc 174:214–222
Li H, Sun X, Zheng T, Xu Z, Song Y, Gu X (2019a) Coumarin-based multifunctional chemosensor for arginine/lysine and Cu2+/Al3+ ions and its Cu2+ complex as colorimetric and fluorescent sensor for biothiols. Sens Actuators B Chem 279:400–409
Li L, Zhang M, Chang K, Kang Y, Ren G, Hou X, Liu W, Wang H, Wang B, Diao H (2019b) A novel fluorescent off–on probe for the sensitive and selective detection of fluoride ions. RSC Adv 9(55):32308–32312
Li S, Cao D, Meng X, Hu Z, Li Z, Yuan C, Zhou T, Han X, Ma W (2020a) A novel fluorescent chemosensor based on coumarin and quinolinyl-benzothiazole for sequential recognition of Cu2+ and PPi and its applicability in live cell imaging. Spectrochim Acta Part A Mol Biomol Spectrosc 230:118022
Li S, Cao D, Meng X, Hu Z, Li Z, Yuan C, Zhou T, Han X, Ma W (2020b) A novel schiff base fluorescent probe based on coumarin and benzothiazole for sequential detection of Al3+ and PPi and its applicability in live cell imaging. J Photochem Photobiol A Chem 392:112427
Lin W, Yuan L, Cao X, Tan W, Feng Y (2008) A Coumarin-based chromogenic sensor for transition-metal ions showing ion-dependent bathochromic shift. Eur J Org Chem 29:4981–4987. https://doi.org/10.1002/ejoc.200800667
Lin Q, Zheng F, Lu T-T, Liu J, Li H, Wei T-B, Yao H, Zhang Y-M (2017) A novel imidazophenazine-based metallogel act as reversible H2PO4− sensor and rewritable fluorescent display material. Sens Actuat B Chem 251:250–255
Liu Z, Peng C, Lu Z, Yang X, Pei M, Zhang G (2015) A novel fluorescent sensor derived from benzimidazo [2, 1-a] benz [de] isoquinoline-7-one-12-carboxylic acid for Cu2+, Cd2+ and PPi. Dyes Pigm 123:85–91
Liu S-Y, Xiong H, Yang J-Q, Yang S-H, Li Y, Yang W-C, Yang G-F (2018) Discovery of butyrylcholinesterase-activated near-infrared fluorogenic probe for live-cell and in vivo imaging. ACS Sens 3(10):2118–2128
Liu S-Y, Xiong H, Li R-R, Yang W-C, Yang G-F (2019) Activity-based near-infrared fluorogenic probe for enabling in vitro and in vivo profiling of neutrophil elastase. Anal Chem 91(6):3877–3884
Long C, Hu J-H, Fu Q-Q, Ni P-W (2019) A new colorimetric and fluorescent probe based on Rhodamine B hydrazone derivatives for cyanide and Cu2+ in aqueous media and its application in real life. Spectrochim Acta Part A Mol Biomol Spectrosc 219:297–306
MacAyeal JR (1999) The comprehensive environmental response, compensation, and liability act: the correct paradigm of strict liability and the problem of individual causation. UCLA J Environ Law Policy 18:217
Machado S, Stawiński W, Slonina P, Pinto AR, Grosso JP, Nouws HPA, Albergaria JT, Delerue-Matos C (2013) Application of green zero-valent iron nanoparticles to the remediation of soils contaminated with ibuprofen. Sci Total Environ 461–462:323–329
Madhu S, Ravikanth M (2014) Boron-dipyrromethene based reversible and reusable selective chemosensor for fluoride detection. Inorg Chem 53(3):1646–1653
Marcu MG, Chadli A, Bouhouche I, Catelli M, Neckers LM (2000) The heat shock protein 90 antagonist novobiocin interacts with a previously unrecognized ATP-binding domain in the carboxyl terminus of the chaperone. J Biol Chem 275(47):37181–37186
Maria JM, Saleta V-R, Andre F, Eugenio U, Lourdes S, Fernanda B (2017) Heterocyclic antioxidants in nature: coumarins. Curr Org Chem 21(4):311–324
Meng X, Li S, Ma W, Wang J, Hu Z, Cao D (2018) Highly sensitive and selective chemosensor for Cu2+ and H2PO4- based on coumarin fluorophore. Dyes Pigm 154:194–198
Mohammad H, Islam ASM, Prodhan C, Chaudhuri K, Ali M (2018) A hydrazone based probe for selective sensing of Al (III) and Al (III)-probe complex mediated secondary sensing of PPi: framing of molecular logic circuit and memory device and computational studies. Photochem Photobiol Sci 17(2):200–212
Myasnikova RM, Davydova TS, Simonov VI (1973) Crystal-structure of coumarin. Kristallografiya 18(4):720–724
Naila A, Meerdink G, Jayasena V, Sulaiman AZ, Ajit AB, Berta G (2019) review on global metal accumulators—mechanism, enhancement, commercial application, and research trend. Environ Sci Pollut Res 26(26):26449–26471
Outten CE, O’Halloran TV (2001) Femtomolar sensitivity of metalloregulatory proteins controlling zinc homeostasis. Science 292(5526):2488–2492
Pankaj W, Priti J, Santosh R, Jadhav HRA (2018) Quinoline, coumarin and other heterocyclic analogs based HIV-1 integrase inhibitors. Curr Drug Discov Technol 15(1):2–19
Purser S, Moore PR, Swallow S, Gouverneur V (2008) Fluorine in medicinal chemistry. Chem Soc Rev 37(2):320–330
Rahman F-U, Ali A, Khalil SK, Guo R, Zhang P, Wang H, Li Z-T, Zhang D-W (2017) Tuning sensitivity of a simple hydrazone for selective fluorescent “turn on” chemo-sensing of Al3+ and its application in living cells imaging. Talanta 164:307–313
Razavi SM (2011) Plant coumarins as allelopathic agents. Int J Biol Chem 5(1):86–90
Reynolds GA, Drexhage KH (1975) New coumarin dyes with rigidized structure for flashlamp-pumped dye lasers. Opt Commun 13(3):222–225
Rivadehi S, Reid EF, Hogan CF, Bhosale SV, Langford SJ (2012) Fluoride-selective optical sensor based on the dipyrrolyl-tetrathiafulvalene chromophore. Org Biomol Chem 10(4):705–709
Sahana A, Banerjee A, Lohar S, Banik A, Mukhopadhyay SK, Safin DA, Babashkina MG, Bolte M, Garcia Y, Das D (2013) FRET based tri-color emissive rhodamine–pyrene conjugate as an Al3+ selective colorimetric and fluorescence sensor for living cell imaging. Dalton Trans 42(37):13311–13314
Salleh WMNHW, Ahmad F (2017) Phytochemistry and biological activities of the genus Ocotea (Lauraceae): a review on recent research results (2000–2016). J Appl Pharm Sci 7(5):204–218
Sarih NM, Ciupa A, Moss S, Myers P, Slater AG, Abdullah Z, Tajuddin HA, Maher S (2020) Furo [3, 2-c] coumarin-derived Fe3+ selective fluorescence sensor: synthesis, fluorescence study and application to water analysis. Sci Rep 10(1):1–11
Schalekamp T, De Boer A (2010) Pharmacogenetics of oral anticoagulant therapy. Curr Pharm Des 16(2):187–203
Sedgwick AC, Wu L, Han H-H, Bull SD, He X-P, James TD, Sessler JL, Tang BZ, Tian H, Yoon J (2018) Excited-state intramolecular proton-transfer (ESIPT) based fluorescence sensors and imaging agents. Chem Soc Rev 47(23):8842–8880
Shan B, Tong X, Xiong W, Qiu W, Tang B, Lu R, Ma W, Luo Y, Zhang S (2015) A new kind of H-acid monoazo-anthraquinone reactive dyes with surprising colour. Dyes Pigm 123:44–54
Shangguan M, Jiang X, Lu Z, Zou W, Chen Y, Xu P, Pan Y, Hou L (2019) A coumarin-based fluorescent probe for hypochlorite ion detection in environmental water samples and living cells. Talanta 202:303–307
Sheng JR, Feng F, Qiang Y, Liang FG, Sen L, Wei F-H (2008) A coumarin-derived fluorescence chemosensors selective for copper (II). Anal Lett 41(12):2203–2213
Shiraishi Y, Yamada C, Hirai T (2019) A coumarin–dihydroperimidine dye as a fluorescent chemosensor for hypochlorite in 99% water. RSC Adv 9(49):28636–28641
Shyamal M, Mazumdar P, Maity S, Sahoo GP, Salgado-Morán G, Misra A (2016) Pyrene scaffold as real-time fluorescent turn-on chemosensor for selective detection of trace-level Al (III) and its aggregation-induced emission enhancement. J Phys Chem A 120(2):210–220
Skalnaya MG, Skalny AV (2018) Essential trace elements in human health: a physician’s view. Publishing House of Tomsk State University, Tomsk, p 224
Stefanachi A, Leonetti F, Pisani L, Catto M, Carotti A (2018) Coumarin: a natural, privileged and versatile scaffold for bioactive compounds. Molecules 23(2):250
Stiefel C, Schubert T, Morlock GE (2017) Bioprofiling of cosmetics with focus on streamlined coumarin analysis. ACS Omega 2(8):5242–5250
Su Z, Chen K, Guo Y, Qi H, Yang X-F, Zhao M (2010) A coumarin-based fluorescent chemosensor for Zn2+ in aqueous ethanol media. J Fluoresc 20(4):851–856
Su Z, Zhang H, Gao Y, Huo L, Wu Y, Ba X (2020) Coumarin-anchored halloysite nanotubes for highly selective detection and removal of Zn (II). Chem Eng J 393:124695
Sui B, Tang S, Liu T, Kim B, Belfield KD (2014) Novel BODIPY-based fluorescence turn-on sensor for Fe3+ and its bioimaging application in living cells. ACS Appl Mater Interfaces 6(21):18408–18412
Sun W, Guo S, Hu C, Fan J, Peng X (2016) Recent development of chemosensors based on cyanine platforms. Chem Rev 116(14):7768–7817
Tang Y, Huang Y, Chen Y, Lu L, Wang C, Sun T, Wang M, Zhu G, Yang Y, Zhang L, Zhu J (2019a) A coumarin derivative as a “turn-on” fluorescence probe toward Cd2+ in live cells. Spectrochim Acta Part A Mol Biomol Spectrosc 218:359–365
Tang Y, Li Y, Han J, Mao Y, Ni L, Wang Y (2019b) A coumarin based fluorescent probe for rapidly distinguishing of hypochlorite and copper (II) ion in organisms. Spectrochim Acta Part A Mol Biomol Spectrosc 208:299–308
Tang X, Zhu Z, Liu R, Ni L, Qiu Y, Han J, Wang Y (2019c) A novel OFF-ON-OFF fluorescence probe based on coumarin for Al3+ and F− detection and bioimaging in living cells. Spectrochim Acta Part A Mol Biomol Spectrosc 211:299–305
Tao P, Chen D, Xu Z, Song Y, Li H, Xian C (2020) A fluorescent probe for the dual detection of mercury ions and thiols based on a simple coumarin derivative. Color Technol 136(1):75–86
Tian G, Zhang Z, Li H, Li D, Wang X, Qin C (2020) Design, synthesis and application in analytical chemistry of photo-sensitive probes based on coumarin. Crit Rev Anal Chem 51:565–581
Ullah I, Li W, Lei S, Zhang Y, Zhang W, Farooq U, Ullah S, Ullah MW, Zhang X (2018) Simultaneous co-substitution of Sr2+/Fe3+ in hydroxyapatite nanoparticles for potential biomedical applications. Ceram Int 44(17):21338–21348
Valente A, Garcia MH (2014) Syntheses of macromolecular ruthenium compounds: a new approach for the search of anticancer drugs. Inorganics 2(1):96–114
Vally H, Misso NLA, Madan V (2009) Clinical effects of sulphite additives. Clin Exp Allergy 39(11):1643–1651
Vedamalai M, Wu SP (2012) A bodipy-based highly selective fluorescent chemosensor for Hg2+ ions and its application in living cell imaging. Eur J Org Chem 6:1158–1163
Vogel A (1820) Darstellung von Benzoesäure aus der Tonka-Bohne und aus den Meliloten-oder Steinklee-Blumen. Ann Phys 64(2):161–166
Wagner BD (2009) The use of coumarins as environmentally-sensitive fluorescent probes of heterogeneous inclusion systems. Molecules 14(1):210–237
Wang S, Men G, Zhao L, Hou Q, Jiang S (2010) Binaphthyl-derived salicylidene Schiff base for dual-channel sensing of Cu, Zn cations and integrated molecular logic gates. Sens Actuat B Chem 145(2):826–831
Wang L, Qin W, Tang X, Dou W, Liu W (2011) Development and applications of fluorescent indicators for Mg2+ and Zn2+. J Phys Chem A 115(9):1609–1616
Wang Y-H, Avula B, Nanayakkara NPD, Zhao J, Khan IA (2013) Cassia cinnamon as a source of coumarin in cinnamon-flavored food and food supplements in the United States. J Agric Food Chem 61(18):4470–4476
Wang L, Fang G, Cao D (2014) A reversible and reusable selective chemosensor for fluoride detection using a phenolic OH-containing BODIPY dye by both colorimetric ‘naked-eye’and fluorometric modes. J Fluoresc 24(6):1757–1766
Wang G-Q, Qin J-C, Li C-R, Yang Z-Y (2015) A highly selective fluorescent probe for Al3+ based on quinoline derivative. Spectrochim Acta Part A Mol Biomol Spectrosc 150:21–25
Wang K, Sun P, Chao X, Cao D, Mao Z, Liu Z (2018a) A coumarin Schiff’s base two-photon fluorescent probe for hypochlorite in living cells and zebrafish. RSC Adv 8(13):6904–6909
Wang C-X, Wu B, Zhou W, Wang Q, Yu H, Deng K, Li J-M, Zhuo R-X, Huang S-W (2018b) Turn-on fluorescent probe-encapsulated micelle as colloidally stable nano-chemosensor for highly selective detection of Al3+ in aqueous solution and living cell imaging. Sens Actuators B Chem 271:225–238
Wang Y, Ma Z-Y, Zhang D-L, Deng J-L, Chen X, Xie C-Z, Qiao X, Li Q-Z, Xu J-Y (2018c) Highly selective and sensitive turn-on fluorescent sensor for detection of Al3+ based on quinoline-base Schiff base. Spectrochim Acta Part A Mol Biomol Spectrosc 195:157–164
Wang Y, Hou X, Li Z, Zhou Q, Lei M, Hu S, Wu X, Li C, Xu Z, Wang Y (2018d) A pyrrole-containing hydrazone and its Cu2+ complex: an easily accessible optical chemosensor system for the successive detection of Zn2+/Cu2+ and pyrophosphate. Anal Methods 10(48):5790–5796
Wang N, Xin C, Li Z, Zhang G, Bai L, Gong Q, Xu C, Han X, Yu C, Li L, Huang W (2019a) A reversible fluorescent probe for directly monitoring protein-small molecules interaction utilizing vibration-induced emission. Dyes Pigm 163:425–432
Wang P, Zhou D, Chen B (2019b) A fluorescent dansyl-based peptide probe for highly selective and sensitive detect Cd2+ ions and its application in living cell imaging. Spectrochim Acta Part A Mol Biomol Spectrosc 207:276–283
Wang K-N, Zhu Y, Xing M, Cao D, Guan R, Zhao S, Liu Z, Mao Z-W (2019c) Two-photon fluorescence probes for mitochondria imaging and detection of sulfite/bisulfite in living cells. Sens Actuators B Chem 295:215–222
Wang X, Ding G, Duan Y, Wang M, Zhu G, Li X, Zhang Y, Qin X (2020) Novel ‘naked-eye’Bis-Schiff base fluorescent chemosensors for sensitive detection of Zn2+ and bio-imaging in living cells. Tetrahedron 76(16):131108
Wilkinsin GR (1976) The manufacture and use of selected inorganic cyanides. Kansas City: Midwest Research Institute (for the US EPA).
Wu J, Sheng R, Liu W, Wang P, Zhang H, Ma J (2012) Fluorescent sensors based on controllable conformational change for discrimination of Zn2+ over Cd2+. Tetrahedron 68(27–28):5458–5463
Wu D, Sedgwick AC, Gunnlaugsson T, Akkaya EU, Yoon J, James TD (2017) Fluorescent chemosensors: the past, present and future. Chem Soc Rev 46(23):7105–7123
Xia Y, Liu X, Wang D, Wang Z, Liu Q, Yu H, Zhang M, Song Y (2018) A fluorometric and mitochondrion-targetable probe for rapid, naked-eye test of hypochlorite in real samples. Chin Chem Lett 29(10):1517–1520
Xie X, Qin Y (2011) A dual functional near infrared fluorescent probe based on the bodipy fluorophores for selective detection of copper and aluminum ions. Sens Actuators B Chem 156(1):213–217
Xie J, Chen C, Ma X, Wu J (2016) Luminescence properties of a thermal-responsive organogel to various metal cations. Inorg Chem Commun 65:41–44
Xie X, Huo F, Chao J, Zhang Y, Yin C (2019) A dual electron-withdrawing enhanced selective/sensitive chemodosimeter for detection on bisulfate and its living cell imaging. Spectrochim Acta Part A Mol Biomol Spectrosc 220:117148
Xin-Mei P, Guri LVD, Cheng HZ (2013) Current developments of coumarin compounds in medicinal chemistry. Curr Pharm Des 19(21):3884–3930
Xu J, Li J, Liu C, Yang L, He G, Ni T, Fan A, Wang S, Wang Q (2019) Design and synthesis of a dinuclear copper (II) probe for selective fluorescence sensing of pyrophosphate. J Sensors 2019. https://doi.org/10.1155/2019/5349124
Yanfang S, Hualai W, Hui B (2020) A coumarin-based turn-on chemosensor for selective detection of Zn(II) and application in live cell imaging. Spectrochim Acta Part A Mol Biomol Spectrosc 228:117746
Yang S, Feng W, Feng G (2018) Development of a near-infrared fluorescent sensor with a large Stokes shift for sensing pyrophosphate in living cells and animals. Anal Chim Acta 1034:119–127
Yang Y-S, Liang C, Yang C, Zhang Y-P, Wang B-X, Liu J (2020) A novel coumarin-derived acylhydrazone Schiff base gelator for synthesis of organogels and identification of Fe3+. Spectrochim Acta Part A Mol Biomol Spectrosc 237:118391
Yin Z-Y, Hu J-H, Gui K, Fu Q-Q, Yao Y, Zhou F-L, Ma L-L, Zhang Z-P (2020) AIE based colorimetric and “turn-on” fluorescence Schiff base sensor for detecting Fe3+ in an aqueous media and its application. J Photochem Photobiol A Chem 396:112542
Young C (2001) Cyanide: social, industrial and economic aspects
Yu W, Qiang J, Yin J, Kambam S, Wang F, Wang Y, Chen X (2014) Ammonium-bearing dinuclear copper (II) complex: a highly selective and sensitive colorimetric probe for pyrophosphate. Org Lett 16(8):2220–2223
Zehra S, Khan RA, Alsalme A, Tabassum S (2019) Coumarin derived “turn on” fluorescent sensor for selective detection of cadmium (II) ion: spectroscopic studies and validation of sensing mechanism by DFT calculations. J Fluoresc 29(4):1029–1037
Zhang B, Diao Q, Ma P, Liu X, Song D, Wang X (2016) A sensitive fluorescent probe for Cu2+ based on rhodamine B derivatives and its application to drinking water examination and living cells imaging. Sens Actuat B Chem 225:579–585
Zhang H-L, Li W-T, Qu W-J, Wei T-B, Lin Q, Zhang Y-M, Yao H (2017) Mercaptooxazole–phenazine based blue fluorescent sensor for the ultra-sensitive detection of mercury(II) ions in aqueous solution. RSC Adv 7(75):47547–47551
Zhang Z, Liu Y, Wang E (2019a) A highly selective “turn-on” fluorescent probe for detecting Cu2+ in two different sensing mechanisms. Dyes Pigm 163:533–537
Zhang Q, Jiao Q, Zhang Q, Liu Z (2019b) A novel crown ether-acylhydrazone turn-on fluorescent chemosensor for Al3+ ion. Spectrochim Acta Part A Mol Biomol Spectrosc 211:1–8
Zhao C, Chen J, Cao D, Wang J, Ma W (2019) Novel coumarin-based containing denrons selective fluorescent chemosesor for sequential recognition of Cu2+ and PPi. Tetrahedron 75(13):1997–2003
Zhou X, Kim J, Liu Z, Jo S, Pak YL, Swamy KMK, Yoon J (2016) Selective fluorescent and colorimetric recognition of cyanide via altering hydrogen bonding interaction in aqueous solution and its application in bioimaging. Dyes Pigm 128:256–262
Zhu G, Huang Y, Wang C, Lu L, Sun T, Wang M, Tang Y, Shan D, Wen S, Zhu J (2019) A novel coumarin-based fluorescence chemosensor for Al3+ and its application in cell imaging. Spectrochim Acta Part A Mol Biomol Spectrosc 210:105–110
Acknowledgements
SA would like to thank to Higher Education Commission for their financial support in the form of NRPU-2017 (Project Number 9922).
Funding
No funding.
Author information
Authors and Affiliations
Contributions
Include all authors.
Corresponding author
Ethics declarations
Conflict of interest
The review article entitled “Recent advancements in fluorescent chemo-sensor for ion detection via coumarin derivatives’’ is carried out with the financial help from Higher Education Commission, Pakistan (Project number: 9922). All the authors involved in the write up of this article do not have any conflict of Interest. The complete details of authors is given as under:
Consent to participate
Not applicable.
Consent for publication
Yes you can publish it.
Ethics approval
Not applicable.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Mansha, A., Asad, S.A., Asim, S. et al. Review of recent advancements in fluorescent chemosensor for ion detection via coumarin derivatives. Chem. Pap. 76, 3303–3349 (2022). https://doi.org/10.1007/s11696-022-02092-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-022-02092-5