Generic placeholder image

Recent Innovations in Chemical Engineering


ISSN (Print): 2405-5204
ISSN (Online): 2405-5212

Review Article

Various Sensing Mechanisms for the Design of Naphthalimide based Chemosensors Emerging in Recent Years

Author(s): Duraisamy Udhayakumari*

Volume 13 , Issue 4 , 2020

Page: [262 - 289] Pages: 28

DOI: 10.2174/2405520413666200217125754

Price: $65


In the design of novel fluorescent chemosensors, investigation of new sensing mechanisms between recognition and signal reporting units is of increasing interest. In recent years, a smart chemosensor probe containing a 1,8-naphthalimide moiety could be developed as a fluorescent and colorimetric sensor for toxic anions, metal ions, biomolecules, nitroaromatics, and acids and be further applied to monitor the relevant biological applications. In this field, several problems and challenges still exist. This critical review is mainly focused on various sensing mechanisms that have emerged in the past few years, such as Photo-Induced Electron Transfer (PET), Intramolecular Charge Transfer (ICT), Fluorescence Resonance Energy Transfer (FRET), Excited-State Intramolecular Proton Transfer (ESIPT), hydrogen bonding and displacement approach. The review concludes with some current and future perspectives, including the use of the naphthalimides for sensing anions, metal ions, biomolecules, nitroaromatics and acids and their potential uses in various fields.

Keywords: Sensing mechanism, chemical sensor, naphthalimide, visual change, bioimaging, fluorescence resonance energy transfer (FRET).

Graphical Abstract
Inamuddin S, Hussain A, Mohammad AK. Zinc selective nano-hybrid cation exchanger carboxymethyl cellulose Zr(IV) tungstate: Sol gel synthesis, physicochemical characterization, & applications. Polym Compos 2017; 38: 2057-66.
Inamuddin TA, Rangreez AK. Synthesis of single-walled carbon nanotubes cerium(IV) phosphate composite cation exchanger: Ion exchange studies & its application as ion-selective membrane electrode for determination of Cd(II) ions. Polym Compos 2017; 38: 1005-13.
Khan AA, Parwaz K, Hussein MA, Neppolian B, Asiri AM. Preparation of new & novel poly(2-anisidine) zirconium tungstate nanocomposite: Thermal, electrical & ion-selective studies. Chin J Chem Eng 2019; 27: 459-66.
Eltayeb NE, Khan A. Design & preparation of a new & novel composite with CNTs & its sensor applications. J Mat Res Technol 2019; 8: 2238-46.
Khan A, Khan AAP, Khan I, et al. Facial synthesis of highly active polymer vanadium molybdate nanocomposite: Improved thermoelectric and antimicrobial studies. J Phys Chem Solids 2019; 131: 148-55.
Bianchi A, Bowman-James K, Garcia-Espana E. Supramolecular chemistry of anions. New York, USA: Wiley-VCH 1997.
Zhou Y, Xu Z, Yoon J. Fluorescent and colorimetric chemosensors for detection of nucleotides, FAD and NADH: highlighted research during 2004-2010. Chem Soc Rev 2011; 40(5): 2222-35.
[] [PMID: 21336366]
Kaur B, Kaur N, Kumar S. Colorimetric metal ion sensors – A comprehensive review of the years 2011-2016. Coord Chem Rev 2018; 358: 13-69.
Akhgari F, Fattahi H, Oskoei YM. Recent advances in nanomaterial-based sensors for detection of trace nitroaromatic explosives, Sens. Actuator B-Chem 2015; 221: 867-78.
Curiel D, Más-Montoya M, Sánchez G. Complexation & sensing of dicarboxylate anions & dicarboxylic acids. Coord Chem Rev 2015; 284: 19-66.
Carter KP, Young AM, Palmer AE. Fluorescent sensors for measuring metal ions in living systems. Chem Rev 2014; 114(8): 4564-601.
[] [PMID: 24588137]
Udhayakumari D, Velmathi S, Venkatesan P, Wu SP. Anthracene coupled thiourea as a colorimetric sensor for F−/Cu2+ & fluorescent sensor for Hg2+/picric acid. J Lumin 2017; 161: 411-6.
Basu A. Metals in medicine: An overview. Sci Rev Chem Commun 2015; 5: 77-87.
Panchenko PA, Fedorova OA, Fedorov YV. Fluorescent & colorimetric chemosensors for cations based on1, 8-naphthalimide derivatives: Design principles & optical signalling mechanisms. Russ Chem Rev 2014; 83: 155-82.
Udhayakumari D, Naha S, Velmathi S. Colorimetric & fluorescent chemosensors for Cu2+. A comprehensive review from the years 2013-2015. Anal Methods 2017; 9: 552-78.
Osredkar J, Sustar N. Copper & zinc, biological role & significance of copper/zinc imbalance. J Clin Toxicol 2011; S3: 1-18.
Willis MS, Monaghan SA, Miller ML, et al. Zinc-induced copper deficiency: a report of three cases initially recognized on bone marrow examination. Am J Clin Pathol 2005; 123(1): 125-31.
[] [PMID: 15762288]
Plum LM, Rink L, Haase H. The essential toxin: impact of zinc on human health. Int J Environ Res Public Health 2010; 7(4): 1342-65.
[] [PMID: 20617034]
Sharma RK, Agrawal M, Marshall F. Heavy metal contamination of soil and vegetables in suburban areas of Varanasi, India. Ecotoxicol Environ Saf 2007; 66(2): 258-66.
[] [PMID: 16466660]
Udhayakumari D. Chromogenic & fluorogenic chemosensors for lethal cyanide ion: A comprehensive review of the year 2016. Sens Actuators B Chem 2018; 259: 1022-57.
Duke RM, Veale EB, Pfeffer FM, Kruger PE, Gunnlaugsson T. Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors. Chem Soc Rev 2010; 39(10): 3936-53.
[] [PMID: 20818454]
Duke RM, Gunnlaugsson T. 3-Urea-1, 8-naphthal-imides are good chemosensors: A highly selective dual colorimetric & fluorescent ICT based anion sensor for fluoride. Tetrahedron Lett 2011; 52: 1503-5.
Li Z, Zhou Y, Yin K, Yu Z, Li Y, Ren J. A new fluorescence turn-on type chemosensor for Fe3+ based on naphthalimide & coumarin. Dyes Pigm 2014; 105: 7-11.
Liu D, Zhu H, Deng X, et al. A 1,8-naphthalimide-based fluorescent sensor with high selectivity and sensitivity for Hg2+ in aqueous solution and living cells. Anal Methods 2019; 11: 3150-4.
Roy S, Saha S, Majumdar R, Dighe RR, Chakravarty AR. Photocytotoxic 3d-metal scorpionates with a 1,8-naphthalimide chromophore showing photoinduced DNA and protein cleavage activity. Inorg Chem 2009; 48(19): 9501-9.
[] [PMID: 19719144]
Veale EB, Frimannsson DO, Lawler M, Gunnlaugsson T. 4-Amino-1,8-naphthalimide-based Tröger’s bases as high affinity DNA targeting fluorescent supramolecular scaffolds. Org Lett 2009; 11(18): 4040-3.
[] [PMID: 19681640]
Dai L, Wu D, Qiao Q, Yin W, Yin J, Xu Z. A naphthalimide-based fluorescent sensor for halogenated solvents. Chem Commun (Camb) 2016; 52(10): 2095-8.
[] [PMID: 26691881]
Zhao LY, Mi QL, Wang GK, et al. 1,8-Naphthalimide-based ‘turn-on’ fluorescent sensor for the detection of zinc ion in aqueous media & its applications for bioimaging. Tetrahedron Lett 2013; (54)2013: 3353-8.
Wang W, Wen Q, Zhang Y, et al. Simple naphthalimide-based fluorescent sensor for highly sensitive and selective detection of Cd2+ and Cu2+ in aqueous solution and living cells. Dalton Trans 2013; 42(5): 1827-33.
[] [PMID: 23165407]
Jia T, Fu C, Huang C, Yang H, Jia N. Highly sensitive naphthalimide-based fluorescence polarization probe for detecting cancer cells. ACS Appl Mater Interfaces 2015; 7(18): 10013-21.
[] [PMID: 25898141]
Grabchev I, Petkov C, Bojinov V. 1,8-Naphthalimides as blue emitting fluorophores for polymer materials. Macromol Mater Eng 2002; 287: 904-8.
McGehee MD, Heeger AJ. Semiconducting (Conjugated) polymers as materials for solid-state lasers. Adv Mater 2000; 12: 1655-68.
Bojinov V, Grabchev I. A new method for synthesis of 4-allyloxy-1,8-naphthalimide derivatives for use as fluorescent bright- enters. Dyes Pigm 2001; 51: 57-61.
Ryan GJ, Quinn S, Gunnlaugsson T. Highly effective DNA photocleavage by novel “rigid” Ru(bpy)(3)-4-nitro- and -4-amino-1,8-naphthalimide conjugates. Inorg Chem 2008; 47(2): 401-3.
[] [PMID: 18078333]
Braña MF, Ramos A. Naphthalimides as anti-cancer agents: synthesis and biological activity. Curr Med Chem Anticancer Agents 2001; 1(3): 237-55.
[] [PMID: 12678756]
Bojinov V, Konstantinova T. Synthesis of polymerizable 1,8-naphthalimidedyes containing hindered amine fragment. Dyes Pigm 2002; 54: 239-45.
Yu MM, Du WW, Zhou W, et al. A 1,8-naphthali-mide-based chemosensor with an off-on fluorescence & lifetime imaging response for intracellular Cr3+ & further for S2¯. Dyes Pigm 2016; 126: 279-85.
Qian X, Xiao Y, Xu Y, Guo X, Qian J, Zhu W. “Alive” dyes as fluorescent sensors: fluorophore, mechanism, receptor and images in living cells. Chem Commun (Camb) 2010; 46(35): 6418-36.
[] [PMID: 20589288]
Tao ZF, Qian X. Naphthalimide hydroperoxides as photonucleases: Substituent effects & structural basis. Dyes Pigm 1999; 43: 139-45.
Xu Z, Yoon J, Spring DR. A selective and ratiometric Cu2+ fluorescent probe based on naphthalimide excimer-monomer switching. Chem Commun (Camb) 2010; 46(15): 2563-5.
[] [PMID: 20461870]
Sun W, Li W, Li J, Zhang J, Du L, Li M. Naphthalimide-based fluorescent off/on probes for the detection of thiols 2012;68 2012; 5363-7.
Choundhary NF, Connelly NG, Hitchcock PB, Leigh GJ. New compounds of tetradentate Schiff bases with vanadium(IV) & vanadium(V). J Chem Soc, Dalton Trans 1999; 4437-46.
Vigato PA, Tamburini S. The challenge of cyclic & acyclic schiff bases & related derivatives. Coord Chem Rev 2004; 248: 1717-2128.
Steven LB, John DL, Gloria H, et al. Syntheses & characterization of gold(III) tetradentate Schiff base complexes. X-ray crystal structures of [Au(sal2pn)] Cl2.5H2O & [Au(sal2en)] PF6. Inorg Chem 2001; 40: 972-6.
Chattopadhyay S, Drew MGB, Ghosh A. Methylene spacer-regulated structural variation in cobalt(ii/iii) complexes with bridging acetate & salen- or salpn-type schiff-base lig. Eur J Inorg Chem 2008; 10: 1693-701.
Lv M, Xu H. Overview of naphthalimide analogs as anticancer agents. Curr Med Chem 2009; 16(36): 4797-813.
[] [PMID: 19929786]
Ingrassia L, Lefranc F, Kiss R, Mijatovic T. Naphthalimides and azonafides as promising anti-cancer agents. Curr Med Chem 2009; 16(10): 1192-213.
[] [PMID: 19355879]
Georgiev NI, Bojinov VB, Nikolov PS. The design, synthesis & photophysical properties of two novel 1,8-naphthalimide fluorescent pH sensors based on PET & ICT. Dyes Pigm 2011; 88: 350-7.
Dimov SM, Georgiev NI, Asiri AM, Bojinov VB. Synthesis and sensor activity of a PET-based 1,8-naphthalimide Probe for Zn(2+) and pH determination. J Fluoresc 2014; 24(6): 1621-8.
[] [PMID: 25199470]
Kurishita Y, Kohira T, Ojida A, Hamachi I. Rational design of FRET-based ratiometric chemosensors for in vitro and in cell fluorescence analyses of nucleoside polyphosphates. J Am Chem Soc 2010; 132(38): 13290-9.
[] [PMID: 20812684]
Yuan X, Xu X, Zhao C, et al. A novel colorimetric & fluorometric fluoride ion probe based on photoinduced electron transfer signaling mechanism. Sens Actuators B Chem 2017; 253: 1096-105.
Wu H-L, Aderinto SO, Xu Y-L, Zhang H, Fan X-Y. A highly selective fluorescent chemosensor for the detection of picrate anion based on 1, 8-naphthalimide derivatives. J Appl Spectrosc 2017; 84: 25-30.
Meka RK, Heagy MD. Selective modulation of ICT & PET processes in N-aryl-1,8-naphthalimide derivatives: Applications in reaction based fluorogenic sensing of sulfide. J Org Chem 2017; 82: 12153-61.
[] [PMID: 29090913]
Xu Y, Mao S, Peng H, et al. A fluorescent sensor for selective recognition of Al3+ based on naphthalimide Schiff-base in aqueous media. J Lumin 2017; 192: 56-63.
Wang F, Xu Y, Aderinto SO, Peng H, Zhang H, Wu H. A new highly effective fluorescent probe for Al3+ ions & its application in practical samples. J Photochem Photobiol Chem 2017; 332: 273-82.
Kavitha R, Stalin T. Dual emission, & pH based naphthalimide derivative fluorescent sensor for the detection of Bi3+. Sens Actuators B Chem 2017; 247: 632-40.
Aderinto SO, New A. Highly potent 1,8-naphthali-mide-based fluorescence “turn off” chemosensor capable of Cu2+ detection in China’s yellow river water samples. J Chin Chem Soc (Taipei) 2017; 64: 1432-45.
Staneva D, Vasileva-Tonkova E, Bosch P, Grabchev I. A new green fluorescent tripod based on 1,8-naphthalimide. Detection ability for metal cations & protons & antimicrobial activity. J Photochem Photobiol Chem 2017; 344: 143-8.
Liu J, Qian Y. A novel pyridylvinyl naphthalimide-rhodamine dye: Synthesis, naked-eye visible & ratiometric chemodosimeter for Hg2+/Fe3+. J Lumin 2017; 187: 33-9.
Hu H, Wang F, Yu L, Sugimura K, Zhou J, Nishio Y. Synthesis of novel fluorescent cellulose derivatives & their applications in detection of nitroaromatic compounds, synthesis of novel fluorescent cellulose derivatives & their applications in detection of nitroaromatic compounds. ACS Sustain Chem& Eng 2017; 6: 1436-45.
Yoon SA, Lee J, Lee MH. A ratiometric fluorescent probe for Zn2+ based on pyrene-appendednaphtha-limide- dipicolylamine. Sens Actuators B Chem 2018; 258: 50-5.
Panchenko PA, Fedorov YV, Fedorova OA. Selective fluorometric sensing of Hg2+ in aqueous solution by the inhibition of PET from dithia-15-crown-5 ether receptor conjugated to 4-amino-1,8-naphthalimide fluorophore. Photochem Photobiol 2018; 364: 124-9.
Bi A, Gao T, Cao X, et al. A novel naphthalimide-based probe for ultrafast, highly selective & sensitive detection of formaldehyde. Sens Actuators B Chem 2018; 255: 3292-7.
Fernandez-Alonso S, Corrales T, Pablos JL, Catalina F. A Switchable fluorescence solid sensor for Hg2+ detection in aqueous media based on a photocrosslinked membrane functionalized with (benzimidazolyl)methyl-piperazine derivative of 1,8-naphthalimide. Sens Actuators B Chem 2018; 270: 256-62.
Lohar S, Maji A, Pal S, et al. Naphthalimide-based turn-on fluorosensor for aqueous sulfide ions for staining in living cells. Chem Select 2017; 2: 9977-83.
Liang X, Xu X, Qiao D, Yin Z, Shang L. The dual mechanism ICT-FRET-based fluorescent probe for the selective detection of hydrogen peroxide. Chem Asian J 2017; 12: 3187-94.
[] [PMID: 29063729]
Li N-N, Zeng S, Li M-Q, et al. A highly selective naphthalimide-based chemosensor: “naked-eye” colorimetric & fluorescent turn-on recognition of Al3+ & its application in practical samples, test paper & logic gate. J Fluoresc 2018; 28(1): 347-57.
[] [PMID: 29143241]
Kang L, Liu Y-T, Li N-N, et al. A schiff-base receptor based naphthalimide derivative: Highly selective & colorimetric fluorescentturn-on sensor for Al3+. J Lumin 2017; 186: 48-52.
Aderinto SO, Xu Y, Peng H. et al A highly selective fluorescent sensor for monitoring Cu2+ ion: Synthesis, characterization & photophysical properties. J Fluoresc 2017; 27(1): 79-87.
[] [PMID: 27639569]
Goel R, Sharma S, Paul K, Luxami V. Naphthalimide based chromo fluorescent sensor & DNA intercalator: Triggered by Hg2+/HSO4– cleavage reaction. Sens Actuators B Chem 2017; 246: 776-82.
Georgiev NI, Dimitrova MD, Krasteva PV, Bojinov VB. A novel water-soluble 1,8-naphthalimide as a fluorescent pH-probe & a molecular logic circuit. J Lumin 2017; 187: 383-91.
Hao Y, Zhang Y, Ruan K, et al. A naphthalimide-based chemodosimetric probe for ratiometric detection of hydrazine. Sens Actuators B Chem 2017; 244: 417-24.
Said AI, Georgiev NI, Bojinov VB. Synthesis of a single 1,8-naphthalimide fluorophore as a molecular logic lab for simultaneously detecting of Fe3+, Hg2+ and Cu2. Spectrochim Acta A Mol Biomol Spectrosc 2018; 196: 76-82.
[] [PMID: 29433042]
Mergu N, Moon JH, Kim H, Heo G, Son Y-A. Highly selective naphthalimide-benzothiazole hybrid-based colorimetric & turn on fluorescent chemosensor for cyanide & tryptophan detection in aqueous media. Sens Actuators B Chem 2018; 273: 143-52.
Bahta M, Ahmed N. A novel 1,8-naphthalimide as highly selective naked-eye & ratiometric fluorescent sensor for detection of Hg2+ ions. Sens Actuators B Chem 2019; 373: 154-61.
Wang W, Mao P-D, Wu W-N, et al. A novel colorimetric & ratiometric fluorescent Cu2+ sensor based on hydrazone bearing 1, 8-naphthalimide & pyrrole moieties. Sens Actuators B Chem 2017; 251: 813-20.
Liu J, Qian Y. A novel naphthalimide-rhodamine dye: Intramolecular fluorescence resonance energy transfer & ratiometric chemodosimeter for Hg2+ & Fe3+. Dyes Pigm 2017; 136: 782-90.
Xu N-Z, Liu M-M, Ye M-A, et al. A Rhodamine-Naphthalimide conjugated chemosensor for ratiometric detection Hg2+ in actual aqueous samples. J Lumin 2017; 188: 135-40.
Liang F-C, Kuo C-C, Chen B-Y, et al. RGB-switchable porous electrospun nanofiber chemoprobe-filter prepared from multifunctional copolymers for versatile sensing of pH & heavy metals. ACS Appl Mater Interfaces 2017; 9(19): 16381-96.
[] [PMID: 28441012]
Liu Y, Zhang J, Wang Y, Liu C, Zhang G, Liu W. A rapid & naked-eye visible FRET ratiometric fluorescent chemosensor for sensitive detection of toxic BF3. Sens Actuators B Chem 2017; 243: 940-5.
Sidhu JS, Singh A, Garg N, Singh N. Carbon dot based, naphthalimide coupled fret pair for highly selective ratiometric detection of thioredoxin reductase & cancer screening. ACS Appl Mater Interfaces 2017; 9(31): 25847-56.
[] [PMID: 28737377]
Kong F, Lin M, Qiu T. Multi-functional ratiometric fluorescent chemosensors of poly(N-isopropylacryl-amide) containing rhodamine 6G & 1,8-naphthali-mide moieties. Polymer (Guildf) 2018; 151: 117-24.
Yuan X, Leng T-H, Guo Z-Q, et al. A FRET-based dual-channel turn-on fluorescence probe for the detection of Hg2+ in living cells. Dyes Pigm 2019; 161: 403-10.
Adhikari S, Ta S, Ghosh A, et al. A 1,8 Naphthalimideanchor Rhodamine B Based FRET Probefor Ratiometric Detection of Cr3+ ion in Living Cells, Photochem Photobiol, A 2019; 372: 49-58.
Sidhu JS, Singh A, Garg N, Kaur N, Singh N. Gold conjugated carbon dots nano assembly: Fret paired fluorescence probe for cysteine recognition. Tetrahedron Lett 2019; 282: 515-22.
Rao C, Cao Z, Chen Y, et al. A new strategy for utilizing activated CH-group to construct a FRET platform for ratiometric sensing of cyanides. Tetrahedron Lett 2019; 6: 178-82.
Satta Y, Nishiyabu R, James TD, Kubo Y. A 1-hydroxy-2, 3, 1-benzodiazaborine-containing p-conjugated system: Synthesis, optical properties & solvent-dependent response toward anions. Tetrahedron 2017; 73: 2053-61.
Devi K, Sarma RJ. Naphthalimide-containing isomeric urea derivatives: Mechanoluminescence & fluoride recognition. Chem Photo Chem 2017; 1: 524-31.
Shumilova TA, Rüffer T, Lang H, Kataev EA. Straightforward design of fluorescent receptors for sulfate: Study of non-covalent interactions contributing to host-guest formation. Chemistry 2018; 24(7): 1500-4.
[] [PMID: 29027757]
Zhang Y, Guo X, Zheng M, et al. A 4,5-quinolimide-based fluorescent sensor for the turn-on detection of Cd2+ with live-cell imaging. Org Biomol Chem 2017; 15(10): 2211-6.
[] [PMID: 28221392]
Cao X, Zhao N, Lv H, et al. Strong blue emissive supramolecular self-assembly system based on naphthalimide derivatives, its ability of detection & removal of 2,4,6-trinitrophenol. Langmuir 2017; 33(31): 7788-98.
[] [PMID: 28718285]
Liu P-X, Chen H, Xu N, et al. A new “turn-on” fluorescent sensor for highly selective sensing of H2PO4. Inorg Chem Commun 2017; 79: 60-4.
Li K-B, Jia W-P, Han D-M, Liang D-X, He X-P, Chen G-R. Fluorogenic bis-triazolyl galactoprobe–metal complex forfull-aqueous analysis of sulfide ion. Sens Actuators B Chem 2017; 246: 197-201.
Li J, Yin C, Liu T, Wen Y, Huo F. A new mechanism-based fluorescent probe for the detection of ClO− by UV–vis, fluorescent spectra & its applications. Sens Actuators B Chem 2017; 252: 1112-7.
Shena S-L, Ning J-Y, Zhang X-F, Miao J-Y, Zhao B-X. Through-bond energy transfer-based ratiometric fluorescent probe for the imaging of HOCl in living cells. Sens Actuators B Chem 2017; 244: 907-13.
Li L, Li H, Liu G, Pu S. A novel fluorescent sensor for Al3+ based on a new diarylethene with a naphthalimide unit. J Photochem Photobiol Chem 2017; 338: 192-200.
Park SY, Kim W, Park S-H, et al. An endoplasmic reticulum-selective ratiometric fluorescent probe for imaging a copper pool. Chem Commun (Camb) 2017; 53(32): 4457-60.
[] [PMID: 28379247]
Kumar A, Chae PS. New 1,8-naphthalimide-conjugated sulfonamide probes for TNP sensing in water. Sens Actuators B Chem 2017; 240: 1-9.
Chen S, Tang Y, Zhan K, Sun D, Hou X. Chemiresistive nanosensors with convex/concave structures. Nano Today 2018; 20: 84-100.
Hou X, Jiang L. Learning from nature: building bio-inspired smart nanochannels. ACS Nano 2009; 3(11): 3339-42.
[] [PMID: 19928930]
Tian Y, Wen L, Hou X, Hou G, Jiang L. Bioinspired ion-transport properties of solid-state single nanochannels and their applications in sensing. ChemPhysChem 2012; 13(10): 2455-70.
[] [PMID: 22715160]
Tang Y, Cao L, Zhan K, et al. Performance analysis of solid state nanopore chemical sensors. Sens Actuators B Chem 2019; 286: 315-20.

Rights & Permissions Print Export Cite as
© 2022 Bentham Science Publishers | Privacy Policy