Abstract
A novel naphthalene based fluorescence probe NBDH was designed and synthesized. Probe NBDH exhibited highly selective and sensitive responses towards Al3+ in HEPES-NaOH buffer solution (pH = 7.4). In addition, the detection of NBDH to Al3+ could be achieved through dual channels embodied in significant fluorescent turn-on signal and ratiometric absorbance response. The stoichiometry ratio of NBDH-Al3+ was 1:1 by fluorescence job’ plot and binging mechanism was further varified by the FT-IR, NMR titration and HRMS. Furthermore, NBDH was achieved in real sample detection, and a series of color test paper were developed for visual detecting Al3+ ions.
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Liu YJ, Tian FF, Fang XY, Jiang FL, Liu Y (2017) Fabrication of an acylhydrazone based fluorescence probe for Al3+. Sensors Actuators B Chem 240:916–925. https://doi.org/10.1016/j.snb.2016.09.051
Sasitharan K, Varghese A, George L (2017) Flavonol based surface modification of doped chalcogenide nanoflakes as an ultrasensitive fluorescence probe for Al3+ ion. Anal Chim Acta 992:94–104. https://doi.org/10.1016/j.aca.2017.08.045
Wen XY, Fan ZF (2016) Linear Schiff-base fluorescence probe with aggregation-induced emission characteristics for Al3+ detection and its application in live cell imaging. Anal Chim Acta 945:75–84. https://doi.org/10.1016/j.aca.2016.09.036
Zhang XX, Wang RJ, Liu G, Fan CB, Pu SZ (2016) A highly selective fluorescence probe for Al3+ based on a new diarylethene with a 6-(hydroxymethyl)picolinohydrazide unit. Tetrahedron 72:8449–8455. https://doi.org/10.1016/j.tet.2016.11.007
Dhineshkumar E, Iyappan M, Anbuselvan C (2018) Turn on macrocyclic chemosensor for Al3+ ion with facile synthesis and application in live cell imaging. Spectrochim Acta A Mol Biomol Spectrosc 199:209–219. https://doi.org/10.1016/j.saa.2018.03.053
Zhu Q, Li L, Mu L, Zeng X, Redshaw C, Wei G (2016) A ratiometric Al3+ ion probe based on the coumarin-quinoline FRET system. J Photochem Photobiol A 328:217–224. https://doi.org/10.1016/j.jphotochem.2016.06.006
Wang Y, Ma ZY, Zhang DL, Deng JL, Chen X, Xie CZ, Qiao X, Li QZ (2018) Xu JY, highly selective and sensitive turn-on fluorescent sensor for detection of Al3+ based on quinoline-base Schiff base. Spectrochim Acta A Mol Biomol Spectrosc 195:157–164. https://doi.org/10.1016/j.saa.2018.01.049
Pang BJ, Li CR, Yang ZY (2018) Design of a colorimetric and turn-on fluorescent probe for the detection of Al (III). J Photochem Photobiol A 356:159–165. https://doi.org/10.1016/j.jphotochem.2017.12046
Wu WN, Mao PD, Wang Y, Zhao XL, Jia L, Xu ZY (2016) Rhodamine 6G hydrazone bearing thiophene unit: a highly sensitive and selective offeon fluorescent chemosensor for Al3+. J Mol Struct 1122:24–28. https://doi.org/10.1016/j.molstruc.2016.05.074
Kumara M, Kumara A, Faizi MSH, Kumara S, Singh MK, Sahu SK, Kishor S, John RP (2018) A selective “turn-on” fluorescent chemosensor for detection of Al3+ in aqueous medium: experimental and theoretical studies. Sensors Actuators B Chem 260:888–899. https://doi.org/10.1016/j.snb.2018.01.098
Li DP, Han XJ, Yan ZQ, Cui Y, Miao JY, Zhao BX (2018) A far-red ratiometric fluorescent probe for SO2 derivatives based on the ESIPT enhanced FRET platform with improved performance. Dyes Pigments 151:95–101. https://doi.org/10.1016/j.dyepig.2017.12.056
Kang L, Xing ZY, Ma XY, Liu YT, Zhang Y (2016) A highly selective colorimetric and fluorescent turn-on chemosensor for Al3+ based on naphthalimide derivative. Spectrochim Acta A Mol Biomol Spectrosc 167:59–65. https://doi.org/10.1016/j.saa.2016.05.030
Li NN, Ma YQ, Zeng S, Liu YT, Sun XJ, Xing ZY (2017) A highly selective colorimetric and fluorescent turn-on chemosensor for Zn2+ and its logic gate behavior. Synth Met 232:17–24. https://doi.org/10.1016/j.synthmet.2017.07.017
Naskar B, Modak R, Sikdar Y, Maiti DK, Bauzá A, Frontera A, Katarkar A, Chaudhuri K, Goswami S (2017) Fluorescent sensing of Al3+ by benzophenone based Schiff base chemosensor and live cell imaging applications: impact of keto-enol tautomerism. Sensors Actuators B Chem 239:1194–1204. https://doi.org/10.1016/j.snb.2016.08.148
Kang L, Liu YT, Li NN, Dang XX, Xing ZY, Li JL, Zhang Y (2017) A schiff-base receptor based naphthalimide derivative: highly selective and colorimetric fluorescent turn-on sensor for Al3+. J Lumin 186:48–52. https://doi.org/10.1016/j.jlumin.2016.12.056
Zhang XX, Wang RJ, Liu G, Fang CB, Pu SZ (2016) A highly selective fluorescence probe for Al3+ based on a new diarylethene with a 6-(hydroxymethyl)picolinohydrazide unit. Tetrahedron 72:8449–8455. https://doi.org/10.1016/j.tet.2016.11.007
Li NN, Zeng S, Li MQ, Ma YQ, Sun XJ, Xing ZY, Li JL (2018) A highly selective naphthalimide-based chemosensor: “naked-eye” colorimetric and fluorescent turn-on recognition of Al3+ and its application in practical samples, test paper and logic gate. J Fluoresc 28:347–357. https://doi.org/10.1007/s10895-017-2197-9
Maniyazagana M, Mariadasseb R, Nachiappanb M, Jeyakanthanb J, Lokanath NK, Naveenc S, Sivaramand G, Muthurajaa P, Manisankar P, Stalina T (2018) Synthesis of rhodamine based organic nanorods for efficient chemosensor probe for Al (III) ions and its biological applications. Sensors Actuators B Chem 254:795–804. https://doi.org/10.1016/j.snb.2017.07.106
Zhou YM, Zhang JL, Zhou H, Hu XY, Zhang L, Zhang M (2013) A highly selective fluorescent probe for Al3+ based on 4-aminoantipyrine. Spectrochim Acta A Mol Biomol Spectrosc 106:68–72. https://doi.org/10.1016/j.saa.2012.12.084
Sen B, Sheet SK, Thounaojam R, Jamatia R, Pal AK, Aguan K, Khatua S (2017) A coumarin based Schiff base probe for selective fluorescence detection of Al3+ and its application in live cell imaging. Spectrochim Acta A Mol Biomol Spectrosc 173:537–543. https://doi.org/10.1016/j.saa.2016.10.005
Diao QP, Ma PY, Lv LL, Li TC, Sun Y, Wang XH, Song DQ (2016) A water-soluble and reversible fluorescent probe for Al3+ and F− in living cells. Sensors Actuators B Chem 229:138–144. https://doi.org/10.1016/j.snb.2016.01.136
Janakipriya S, Chereddy NR, Korrapati P, Thennarasu S, Mandal AB (2016) Selective interactions of trivalent cations Fe3+, Al3+ and Cr3+ turn on fluorescence in a naphthalimide based single molecular probe. Spectrochim Acta A Mol Biomol Spectrosc 153:465–470. https://doi.org/10.1016/j.saa.2015.08.044
Yue XL, Li CR, Yang ZY (2017) A novel Schiff-base fluorescent probe based on 1,8-naphthyridine and naphthalimide for Al3+. Inorg Chim Acta 464:167–171. https://doi.org/10.1016/j.ica.2017.05.032
Gupta A, Kumar N (2016) A review of mechanisms for fluorescent “turn-on” probes to detect Al3+ ions. RSC Adv 6:106413–106434. https://doi.org/10.1039/c6ra23682k
Wang RJ, Wang NS, Pu SZ, Zhang XX, Liu G, Dai YF (2017) A acid/base gated photochromic and fluorescent sensor based on a diarylethene with a 2-(1H-dithienobenzoimidazole)phenol unit. Dyes Pigments 146:445–454. https://doi.org/10.1016/j.dyepig.2017.07.036
Liu HY, Zhang BB, Tan CY, Liu F, Cao JK, Tan Y, Jiang YY (2016) Simultaneous bioimaging recognition of Al3+ and Cu2+ in living-cell, and further detection of F− and S2− by a simple fluorogenic benzimidazole-based chemosensor. Talanta 161:309–319. https://doi.org/10.1016/j.talanta.2016.08.061
Feng ET, Lu RM, Fan CB, Zheng CH, Pu SZ (2017) A fluorescent sensor for Al3+ based on a photochromic diarylethene with a hydrazinobenzothiazole Schiff base unit. Tetrahedron Lett 58:1390–1394. https://doi.org/10.1016/j.tetlet.2017.02.067
Maniyazagan M, Mariadasse R, Nachiappan M, Jeyakanthan J, Lokanathc NK, Naveen S, Sivaraman G, Muthuraja P, Manisankar P, Stalin T (2018) Synthesis of rhodamine based organic nanorods for efficientchemosensor probe for Al (III) ions and its biological applications. Sensors Actuators B Chem 254:795–804. https://doi.org/10.1016/j.snb.2017.07.106
Singh R, Samanta S, Mullick P, Ramesh A, Das G (2018) Al3+ sensing through different turn-on emission signals Vis-a-Vis two different excitations: applications in biological and environmental realms. Anal Chim Acta 1025:172–180. https://doi.org/10.1016/j.aca.2018.03.053
Sarkar D, Ghosh P, Gharami S, Mondal TK, Murmu N (2017) A novel coumarin based molecular switch for the sequential detectionof Al3+ and F−: application in lung cancer live cell imaging andconstruction of logic gate. Sensors Actuators B Chem 242:338–346. https://doi.org/10.1016/j.snb.2016.11.059
Liao Z, Liu Y, Han SF, Wang D, Zheng JQ, Zheng XJ, Jin LP (2017) A novel acylhydrazone-based derivative as dual-mode chemosensorfor Al3+, Zn2+ and Fe3+ and its applications in cell imaging. Sensors Actuators B Chem 244:914–921. https://doi.org/10.1016/j.snb.2017.01.074
Yao DH, Huang XW, Guo FQ, Xie PH (2018) A new fluorescent enhancement chemosensor for Al3+ and Fe3+ based on naphthyridine and benzothiazole groups. Sensors Actuators B Chem 256:276–281. https://doi.org/10.1016/j.snb.2017.10.080
Rai A, Singh AK, Tripathi K, Sonkar AK, Chauhan BS, Srikrishna S, James TD, Mishra L (2018) A quick and selective rhodamine based “smart probe” for “signal-on”optical detection of Cu2+ and Al3+ in water, cell imaging, computational studies and solid state analysis. Sensors Actuators B Chem 266:95–105. https://doi.org/10.1016/j.snb.2018.02.019
Sen B, Sheet SK, Thounaojam R, Jamatia R, Pal AK, Aguan K, Khatua S (2017) A coumarin based Schiff base probe for selective fluorescence detection of Al3+ and its application in live cell imaging. Spectrochim Acta A Mol Biomol Spectrosc 173:537–543. https://doi.org/10.1016/j.saa.2016.10.005
Yue XL, Wang ZQ, Li CR, Yang ZY (2018) A highly selective and sensitive fluorescent chemosensor and its application for rapid on-site detection of Al3+. Spectrochim Acta A Mol Biomol Spectrosc 193:415–421. https://doi.org/10.1016/j.saa.2017.12.053
Xu JC, Zhang Y, Zeng LT, Liu JB, Kinsella JM, Sheng RL (2016) A simple naphthalene-based fluorescent probe for high selective detection of formaldehyde in toffees and HeLa cells via aza-cope reaction. Talanta 160:645–652. https://doi.org/10.1016/j.talanta.2016.08.010
Santhoshkumar S, Velmurugan K, Prabhu J, Radhakrishnan G, Nandhakumar R (2016) A naphthalene derived Schiff base as a selective fluorescent probe for Fe2+. Inorg Chim Acta 439:1–7. https://doi.org/10.1016/j.ica.2015.09.030
Sahana A, Banerjee A, Lohar S, Das S, Hauli I, Mukhopadhyay SK, Matalobos JS, Das D (2013) Naphthalene based highly selective OFF-ON-OFF type fluorescent probe for Al3+ and NO2 ions for living cell imaging at physiological pH. Inorg Chim Acta 398:64–71. https://doi.org/10.1016/j.ica.2012.12.012
Yue XL, Wang ZQ, Li CR, Yang ZY (2017) Naphthalene-derived Al3+-selective fluorescent chemosensor based on PET and ESIPT in aqueous solution. Tetrahedron Lett 58:4532–4537. https://doi.org/10.1016/j.tetlet.2017.10.044
Qin JC, Yang ZY, Yang P (2015) Recognition of Al3+ based on a naphthalene-based “off–on” chemosensor in near 100% aqueous media. Inorg Chim Acta 432:136–141. https://doi.org/10.1016/j.ica.2015.03.029
Roy A, Dey S, Halder S, Roy P (2017) Development of a new chemosensor for Al3+ ion: tuning of properties. J Lumin 192:504–512. https://doi.org/10.1016/j.jlumin.2017.07.020
Wang QM, Sun HF, Jin L, Wang WL, Zhang ZH, Chen YL (2018) A novel turn on and reversible sensor for Al3+ and its applications in bioimaging. J Lumin 203:113–120. https://doi.org/10.1016/j.jlumin.2018.06.047
Zhu JL, Zhang YH, Wang L, Sun TM, Wang M, Wang YP, Ma DY, Yang QQ, Tang YF (2016) A simple turn-on Schiff base fluorescence sensor for aluminum ion. Tetrahedron Lett 57:3535–3539. https://doi.org/10.1016/j.tetlet.2016.06.112
Das B, Dey S, Maiti GP, Bhattacharjee A, Dhara A, Jana A (2018) Hydrazinopyrimidine derived novel Al3+ chemosensor: molecular logic gate and biological applications. New J Chem 42:9424–9435. https://doi.org/10.1039/c7nj05095j
Jo TG, Jung JM, Han J, Lim MH, Kim C (2017) A single fluorescent chemosensor for multiple targets of Cu2+, Fe2+/3+ and Al3+ in living cells and a near-perfect aqueous solution. RSC Adv 7:28723–28732. https://doi.org/10.1039/c7ra05565j
Wen XY, Fan ZF (2016) Linear Schiff-base fluorescence probe with aggregation-induced emission characteristics for Al3+ detection and its application in live cell imaging. Anal Chim Acta 945:75–84. https://doi.org/10.1016/j.aca.2016.09.036
Li CR, Li SL, Yang ZY (2016) A chromone-derived Schiff-base as Al3+ “turn-on” fluorescent probe based on photoinduced electron-transfer (PET) and C=N isomerization. Tetrahedron Lett 57:4898–4904. https://doi.org/10.1016/j.tetlet.2016.09.058
Yue XL, Li CR, Yang ZY (2017) A novel Schiff-base fluorescent probe based on 1,8-naphthyridine and naphthalimide for Al3+. Inorg Chim Acta 464:167–171. https://doi.org/10.1016/j.ica.2017.05.032
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+. Sensors Actuators B Chem 239:1109–1117. https://doi.org/10.1016/j.snb.2016.08.093
Naskar B, Modak R, Sikdar Y, Maiti DK, Bauzá A, Frontera A, Katarkar A, Chaudhuri K, Goswami S (2017) Fluorescent sensing of Al3+ by benzophenone based Schiff base chemosensor and live cell imaging applications: impact of keto-enol tautomerism. Sensors Actuators B Chem 239:1194–1204. https://doi.org/10.1016/j.snb.2016.08.148
Li W, Tian XH, Huang B, Li HJ, Zhao XY, Gao S, Zheng J, Zhang XZ, Zhou HP, Tian YP, Wu JY (2016) Triphenylamine-based Schiff bases as the high sensitive Al3+ or Zn2+ fluorescence turn-on probe: mechanism and application in vitro and in vivo. Biosens Bioelectron 77:530–536. https://doi.org/10.1016/j.bios.2015.09.059
Sheet SK, Sen B, Thounaojam R, Aguan K, Khatua S (2017) Highly selective light-up Al3+ sensing by a coumarin based Schiff base probe: subsequent phosphate sensing DNA binding and live cell imaging. J Photochem Photobiol A 332:101–111. https://doi.org/10.1016/j.jphotochem.2016.08.019
Pang BJ, Li CR, Yang ZY (2018) Design of a colorimetric and turn-on fluorescent probe for the detection of Al (III). J Photochem Photobiol A 356:159–165. https://doi.org/10.1016/j.jphotochem.2017.12.046
Wang Q, Wen XY, Fan ZF (2018) A Schiff base fluorescent chemsensor for the double detection of Al3+ and PPi through aggregation induced emission in environmental physiology. J Photochem Photobiol A 358:92–99. https://doi.org/10.1016/j.jphotochem.2018.03.004
Sen B, Sheet SK, Thounaojam R, Jamatia R, Pal AK, Aguan K, Khatua S (2017) A coumarin based Schiff base probe for selective fluorescence detection of Al3+ and its application in live cell imaging. Spectrochim Acta A Mol Biomol Spectrosc 173:537–543. https://doi.org/10.1016/j.saa.2016.10.005
Tajbakhsh M, Chalmardi GB, Bekhradnia A, Hosseinzadeh R, Hasani N, Amiri MA (2018) A newfluorene-based Schiff-base as fluorescent chemosensor for selective detection of Cr3+ and Al3+. Spectrochim Acta A Mol Biomol Spectrosc 189:22–31. https://doi.org/10.1016/j.saa.2017.08.007
Wang Y, Ma ZY, Zhang DL, Deng JL, Chen X, Xie CZ, Qiao X, Li QZ, Xu JY (2018) Highly selective and sensitive turn-on fluorescent sensor for detection of Al3+ based on quinoline-base Schiff base. Spectrochim Acta A Mol Biomol Spectrosc A 195:157–164. https://doi.org/10.1016/j.saa.2018.01.049
Qin JC, Cheng XY, Fang R, Wang MF, Yang ZY, Li TR, Li Y (2016) Two Schiff-base fluorescent sensors for selective sensing of aluminum (III): experimental and computational studies. Spectrochim Acta A Mol Biomol Spectrosc A 152:352–357. https://doi.org/10.1016/j.saa.2015.07.095
Zeng S, Li SJ, Sun XJ, Li MQ, Ma YQ, Xing ZY, Li JL (2018) A naphthalene-quinoline based chemosensor for fluorescent “turn-on” and absorbance-ratiometric detection of Al3+ and its application in cells imaging. Spectrochim Acta A Mol Biomol Spectrosc A 205:276–286. https://doi.org/10.1016/j.saa.2015.07.095
Tong L, Qian Y (2019) A naphthalimide–rhodamine chemodosimeter for hypochlorite based on TBET: high quantum yield and endogeous imaging in living cells. J Photochem Photobiol A 368:62–69. https://doi.org/10.1016/j.jphotochem.2018.09.027
Olmsted J (1979) Calorimetric determinations of absolute fluorescence quantum yields. J Phys Chem 83:2581–2584. https://doi.org/10.1021/j100483a006
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This work was supported by by the Research Science Foundation in Technology Innovation of Harbin (No. 2017RAQXJ022) and Postdoctoral Scientific Research Developmental Fund of Heilongjiang Province (No. LBH-Q14023).
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Sun, XJ., Ma, YQ., Fu, H. et al. A Highly Selective Fluorescence “Turn on” and Absorbance-Ratiometric Detection of Al3+ in Totally H2O and its Application in Test Paper. J Fluoresc 29, 577–586 (2019). https://doi.org/10.1007/s10895-019-02374-4
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DOI: https://doi.org/10.1007/s10895-019-02374-4