Abstract
A novel diarylethene-based fluorescent chemosensor containing a quinoline unit (1o) had been designed and synthesized. 1o showed good photochromic ability and fluorescence switching properties by alternating UV/vis light irradiation. The chemosensor showed high “Turn-off” fluorescent selectivity for Hg2+ by competitive tests of the fluorescence reaction in the presence other ions in acetonitrile solution. The stoichiometry between the compound 1o and Hg2+ was 1:1 by Job’s plot curve and HRMS analysis. In addition, the LOD for Hg2+ was calculated as 60 nM. The fluorescence emission can be back to the “Turn-on” state by adding EDTA. Based on these facts, a molecular logic gate that including four input signals (UV/vis and Hg2+/EDTA) and one output signal (fluorescent intensity at 491 nm) was designed.
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References
Maiti S, Prins LS (2017) A modular self-assembled sensing system for heavy metal ions with tunable sensitivity and selectivity. Tetrahedron 73:4950–4954
Li XM, Li X, Zhao H, Kang HM, Fan CB, Liu G, Pu SZ (2021) A novel diarylethene-rhodamine unit based chemosensor for fluorimetric and colorimetric detection of Hg2+. J Flouresc 31:1513–1523
Govindasamy V, Perumal S, Sekar I, Madheswaran B, Karuppannan S, Kuppannan SB (2021) Phenothiazine-thiophene hydrazide dyad: An efficient On-Off chemosensor for highly selective and sensitive detection of Hg2+ Ions. J Flouresc 31:667–674
Pan ZX, Xu ZX, Chen J, Hu LP, Li HQ, Zhang X, Gao XC, Wang MX, Zhang J (2020) Coumarin thiourea-based fluorescent turn-on Hg2+ probe that can be utilized in a broad pH range 1–11. J Flouresc 30:505–514
Vijayan AN, Liu ZM, Zhao HH, Zhang P (2019) Nicking enzyme-assisted signal-amplifiable Hg2+ detection using upconversion nanoparticles. Anal Chim Acta 1072:75–80
Zhao YP, Ma YY, Lin WY (2019) A near-infrared and two-photon ratiometric fluorescent probe with a large Stokes shift for sulfur dioxide derivatives detection and its applications in vitro and in vivo. Sensor Actuat B Chem 288:519–526
Zhang Y, Zeng GM, Tang L, Li YP, Chen ZM, Huang GH (2014) Quantitative detection of trace mercury in environmental media using a three-dimensional electrochemical sensor with an anionic intercalator. RSC Adv 4:18485–18492
Duan JL, Zhan JH (2015) Recent developments on nanomaterials-based optical sensors for Hg2+ detection. Sci China Mater 58:223–240
Chen GY, Wang W, Yuan Y, Dong J, Cui X, Huang X, Deng Y, Tang Z (2020) Ion-induced PCR strategy for mercury detection. Electrophoresis 41:1517–1522
Atta BM, Saleem M, Ali H, Bilal M, Fayyaz M (2020) Application of fluorescence spectroscopy in wheat crop: Early disease detection and associated molecular changes. J Flouresc 30:801–810
Rambabu A, Ganji N, Daravath S, Ramesh G (2020) An investigation on DNA binding, cleavage and antimicrobial properties of mononuclear Co(II), Ni(II) and Cu(II) complexes derived from N, O Donor Schiff Bases. J Flouresc 30:1397–1410
Carter KP, Young AM, Palmer AE (2014) Fluorescent sensoes for measuring metal ions in living systems. Chem Rev 114:4564–4601
Ruan YB, Xie J (2011) Unexpected highly selective fluorescence turn-on and ratiometric detection of Hg2+ based on fluorescein platform. Tetrahedron 67:8717–8723
Jung M, Kim C, Harrison RG (2018) A dual sensor selective for Hg2+ and cysteine detection. Sensor Actuat B Chem 225:2756–2763
Wang QF, Xu YF, Hou YH, Wang YF, Yan MH, Zhang XY, Wang H (2016) Highly sensitive and selective fluorescence detection of Hg(II) ions based on R-phycoerythrin from Porphyra yezoensis. RSC Adv 6:114685–114689
Yin PC, Niu QF, Yang QS, Lan LX, Li TD (2019) A new naked-eye colorimetric and ratiometric fluorescent sensor for imaging Hg2+ in living cells. Tetrahedron 75:130687
Jin JY, Li X, Zhang JJ, Zhao P, Tian H (2013) Rational design of double-check mercury ion chemosensors based on photochromic compounds. Isr J Chem 53:288–293
Lee JH, Paik HM, Jang SP, Eom GH, Bae JM, Kim C, Kim Y, Kim SJ (2012) Construction of Hg-II complexes containing chelating 2,2’-dipyridylamine ligands: Anion effect, photoluminescence and catalytic activities. Inorg Chem Commun 15:212–215
Xi HC, Zhang ZP, Zhang WW, Li MQ, Lian C, Luo QF, Tian H, Zhu WH (2019) All-visible-light-activated dithienylethenes induced by intramolecular proton transfer. J Am Chem Soc 141:18467–18474
Chen SJ, Li WL, Li X, Zhu WH (2017) Aggregation-controlled photochromism based on a dithienylethene derivative with aggregation-induced emission. J Mater Chem C 5:2717–2722
Chen SJ, Guo ZQ, Zhu SQ, Shi WE, Zhu WH (2013) A multiaddressable photochromic bisthienylethene with sequence-dependent responses: Construction of an INHIBIT logic gate and a kepad lock. ACS Appl Mater Inter 5:5623–5629
Zhu WH, Song LW, Yang YH, Tian H (2012) Novel bisthienylethene containing ferrocenyl-substituted naphthalimide: A photo- and redox multi-addressable molecular switch. Eur J Histochem 18:13388–13394
Chen X, Zhu LL, Wang DL, Zou Q, Li X, Chen WB (2019) A unimolecular platform based on diarylethene with multiple stimuli-gated photochromism. Dyes Pigm 164:91–96
Wang S, Ding HC, Wang YS, Fan CB, Liu G, Pu SZ (2019) Novel multi-responsive fluorescence switch for Hg2+ and UV/vis lights based on diarylethene-rhodamine derivative. Tetrahedron 75:1517–1524
Zou Q, Li X, Agren H (2014) Configurable photochromism of an unsymmetrical dithienylethene derivative by Cu2+ ions or water. Dyes Pigm 111:1–7
Zou Q, Li X, Zhou J, Bai KK, Agren H (2014) Synthesis and photochromism of a spirooxazine derivative featuring a carbazole moiety: Fast thermal bleaching and excellent fatigue resistance. Dyes Pigm 107:174–181
Weng T, Zhang K, Wu B, Chen X, Zou Q, Zeng T, Zhu L (2019) Orthogonally incorporating dual-fluorescence control into gated photochromism for multifunctional molecular switching. Chem Eur J 25(67):15281–15287
Wang ZH, Zheng CH, Xu DM, Liao GM, Pu SZ (2021) A fluorescent sensor for Zn2+ and Cd2+ based on a diarylethene derivative with an indole-2-methylhydrazone moiety. J Photochem Photobiol A 424:113634
Zhang HF, Yin CX, Liu T, Zhang YB, Huo FJ (2017) Turn-on fluorescent probe detection of Ca2+ ions and applications to bioimaging. Spectrochim Acta A 180:211–216
Jiao Y, Liu X, Zhou L, He HY, Zhou P, Duan CY (2017) A schiff-base dual emission ratiometric fluorescent chemosensor for Hg2+ ions and its application in cellular imaging. Sensor Actuat B Chem 247:950–956
Feng YS, Kuai ZY, Song Y, Guo J, Yang QB, Shan YM, Li YX (2017) A novel turn-on thiooxofluorescein-based colorimetric and fluorescent sensor for Hg2+ and its application in living cells. Talanta 170:103–110
Miao ZR, Reisz JA, Mitroka SM, Pan J, Xian M, King SB (2015) A selective phosphine-based fluorescent probe for nitroxyl in living cells. Bioorg Med Chem Lett 25:16–19
Wu YL, Huang S, Zeng F, Wang J, Yu CM, Huang J, Xie HT, Wu SZ (2015) A ratiometric fluorescent system for carboxylesterase detection with AIE dots as FRET donors. Chem Commun 51:12791–12794
Li SS, Cao DL, Meng XJ, Hu ZY, Li ZC, Yuan CC, Zhou T, Han XH, Ma WB (2020) A novel fluorescent sensor for specific recognition of GSH based on the copper complex and its bioimaging in living cells. W B Bioorg Chem 10:18434–18439
Kawai S, Nakashima T, Atsumi K, Sakai T, Harigai M, Imamoto Y, Kamikubo H, Kataoka M, Kawai T (2007) Novel photochromic molecules based on 4,5-dithienyl thiazole with fast thermal bleaching rate. Chem Mater 19:3479–3483
Shahab S, Filippovich L, Kumar R, Darroudi M, Borzehandani MY, Gomar M, Hajikolaee FH (2015) Photochromic properties of the molecule Azure A chloride in polyvinyl alcohol matrix. J Mol Struct 1101:109–115
Chen LL, Zhang JQ, Wang QC, Zou L (2015) Photo-controllable and aggregation-induced emission based on photochromic bithienylethene. Dyes Pigm 123:112–115
Zhang LL, Zhu HK, Zhao CC, Gu XF (2017) A near-infrared fluorescent probe for monitoring fluvastatin-stimulated endogenous H2S production. Chin Chem Lett 28:218–221
Zhu LM, Xu JC, Sun Z, Fu BQ, Qin CQ, Zeng LT, Hu XC (2015) A twisted intramolecular charge transfer probe for rapid and specific detection of trace biological SO2 derivatives and bio-imaging applications. Chem Commun 51:1154–1156
Zhang T, Wu BY, Zou ZZ, Wu YX, Zheng JD, Wong WK, Wong KL (2016) A reversible biocompatible turn-on fluorescent probe for the detection of mercury (II). Luminescence 170:187–193
Hong MM, Lu SZ, Lv F, Xu DM (2016) A novel facilely prepared rhodamine-based Hg2+ fluorescent probe with three thiourea receptors. Dyes Pigm 127:94–99
Maity SB, Banerjee S, Sunwoo K, Kim JS, Bharadwaj PK (2015) A fluorescent chemosensor for Hg2+ and Cd2+ ions in aqueous medium under physiological pH and Its applications in imaging living cells. Inorg Chem 54:3929–3936
Yan FY, Cao DL, Yang N, Yu QH, Wang M, Chen L (2012) A selective turn-on fluorescent chemosensor based on rhodamine for Hg2+ and its application in live cell imaging. Sensor Actuat B Chem 162:313–320
Acknowledgements
The authors are grateful for financial support from the National Natural Science Foundation of China (41867052, 21861017, 41867053), the Project of the Science Fund of Jiangxi Education Office (GJJ211135), and the Scientific Research Foundation for PhD of Jiangxi Science and Technology Normal University (2021BSQD34).
Funding
This work was supported by the National Natural Science Foundation of China (41867052, 21861017, 41867053), the Project of the Science Fund of Jiangxi Education Office (GJJ211135), and the Scientific Research Foundation for PhD of Jiangxi Science and Technology Normal University (2021BSQD34).
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Mao, L., Li, X., Ding, H. et al. A Highly Selective Hg2+ Fluorescent Chemosensor Based On Photochromic Diarylethene With Quinoline Unit. J Fluoresc 32, 2119–2128 (2022). https://doi.org/10.1007/s10895-022-02930-5
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DOI: https://doi.org/10.1007/s10895-022-02930-5