Synthesis and ultraviolet/aggregation-induced emission investigation of novel tetraphenylvinyl hydrazone derivatives: efficient multimodal chemosensors for fluoride ion

Abstract

Herein, three novel tetraphenylethylene hydrazone chemosensors TC12, SC16, and TC16 are prepared for the selective detection of F⁻. Two NH and one C=N units are incorporated into the sensors for better colorimetric responses, whereas the tetraphenyl unit is in charge of the aggregation-induced emission effect. Among them, compounds SC16 and TC16 form stable gels with some organic solvents. All the tetrahydrofuran/H₂O solutions of the three compounds exhibit aggregation-induced emission effect, whereby the fluorescence emission increases by varying degrees with the volume of poor solvent water. Moreover, good aggregation-induced emission effects are observed in the self-assembly of SC16 and TC16. As a sample chemosensor, TC12 in tetrahydrofuran responds to F⁻ selectively with high sensitivity, with the colorimetric and fluorometric detection limits of 8.25 × 10⁻⁷ mol·L^–1 and 2.69 × 10⁻⁷ mol·L^–1, respectively. The reversible gel-sol-gel phase transition and color changes indicate that both SC16-dimethyl sulfoxide and TC16-ethyl acetate gels specifically respond to F^– with good sensitivity. The detection results are well supported by ultraviolet-visible spectroscopy, fluorescent spectroscopy, and ¹H nuclear magnetic resonance. More importantly, the driving forces of gelation are visually clarified through the single crystal X-ray analysis of compound TOMe.

Graphical abstract

Keywords

organogelator / tetraphenylvinyldrazone / single crystal / aggregation-induced emission effect / ion sensing

References

[1] Ning K, Zheng S, He Y, Hu Y, Hao S, Cui Q, Chen H. Removal of fluoride from aqueous solutions through Fe(III) modified water treatment residues. Journal of Cleaner Production, 2023, 382: 135374

[2] Kang H, Zhang D, Chen X, Zhao H, Yang D, Li Y, Bao M, Wang Z. Preparation of MOF/polypyrrole and flower-like MnO₂ electrodes by electrodeposition: high-performance materials for hybrid capacitive deionization defluorination. Water Research, 2023, 229: 119441

[3] Hao C, Wang Y, He K, Gui H. Seasonal distribution of deep groundwater fluoride, geochemical factors and ecological risk for irrigation in the Shendong mining area, China. Frontiers in Environmental Science, 2022, 10: 1024797

[4] Tipping W J, Wilson L T, Blaseio S K, Tomkinson N C O, Faulds K, Graham D. Ratiometric sensing of fluoride ions using Raman spectroscopy. Chemical Communications, 2020, 56(92): 14463–14466

[5] Sahu S, Sikdar Y, Bag R, Maiti D K, Ceron-Carrasco J P, Goswami S. Visual detection of fluoride ion based on ICT mechanism. Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy, 2019, 213: 354–360

[6] Katiyar P, Pandey N, Sahu K K. Biological approaches of fluoride remediation: potential for environmental clean-up. Environmental Science and Pollution Research International, 2020, 27(12): 13044–13055

[7] Zhang L, Gao X, Chen X, Zhao M, Wu H, Liu Y. A smartphone integrated ratiometric fluorescent sensor for point-of-care testing of fluoride ions. Analytical and Bioanalytical Chemistry, 2022, 414(13): 3999–4009

[8] Sasaki Y, Lyu X, Zhang Z, Minami T. A minimized fluorescent chemosensor array utilizing carboxylate-attached polythiophenes on a chip for metal ions detection. Frontiers of Chemical Science and Engineering, 2022, 16(1): 72–80

[9] Zhou L, Chen Y, Shao B, Cheng J, Li X. Recent advances of small-molecule fluorescent probes for detecting biological hydrogen sulfide. Frontiers of Chemical Science and Engineering, 2022, 16(1): 34–63

[10] Park S, Ju J, Lee Y J, Lee S Y. A hydrazide organogelator for fluoride sensing with hyperchromicity and gel-to-sol transition. RSC Advances, 2020, 10(24): 14243–14248

[11] Razi S S, Gupta R C, Ali R, Dwivedi S K, Srivastava P, Misra A. A new D-π-A type intramolecular charge transfer Dyad system to detect F⁻: anion induced CO₂ sensing. Sensors and Actuators. B, Chemical, 2016, 236: 520–528

[12] Zhou Y, Wang X, Zhang W, Tang B, Li P. Recent advances in small molecule fluorescent probes for simultaneous imaging of two bioactive molecules in live cells and in vivo. Frontiers of Chemical Science and Engineering, 2022, 16(1): 4–33

[13] Panja S, Adams D J. Stimuli responsive dynamic transformations in supramolecular gels. Chemical Society Reviews, 2021, 50(8): 5165–5200

[14] Huang Y, Yuan Y, Tu W, Zhang Y, Zhang M, Qu H. Preparation of efficient organogelators based on pyrazine-2,5-dicarboxylic acid showing room temperature mesophase. Tetrahedron, 2015, 71(21): 3221–3230

[15] Zhu M, Zhong M, Chen M, Huang S, Li Y, Cao F. A π-conjugated α-cyanostilbene dimer emitting strongly red fluorescence with a large Stokes’ shift of ca. 300 nm and used as a probe for selective detection of Cu²⁺. Optical Materials, 2022, 125: 112059

[16] Yadav E, Khatana A K, Sebastian S, Gupta M K. DAP derived fatty acid amide organogelators as novel carrier for drug incorporation and pH-responsive release. New Journal of Chemistry, 2021, 45(1): 415–422

[17] Sun H, Chuai J, Wei H, Zhang X, Yu H. Multi-functional organic gelator derived from phenyllactic acid for phenol removal and oil recovery. Journal of Hazardous Materials, 2019, 366: 46–53

[18] Wang N, Yao H, Tao Q, Sun J, Ma H, Wang Y, Zhou C, Fan H, Shao H, Qin A, Su D, Wang C, Chong H. TPE based aggregation induced emission fluorescent sensors for viscosity of liquid and mechanical properties of hydrogel. Chinese Chemical Letters, 2022, 33(1): 252–256

[19] Li J, Wang J, Li H, Song N, Wang D, Tang B. Supramolecular materials based on AIE luminogens (AIEgens): construction and applications. Chemical Society Reviews, 2020, 49(4): 1144–1172

[20] Chen Y, Lam J W Y, Kwok R T K, Liu B, Tang B Z. Aggregation-induced emission: fundamental understanding and future developments. Materials Horizons, 2019, 6(3): 428–433

[21] Wang H, Liu Q, Hu Y, Liu M, Huang X, Gao W, Wu H. A multiple stimuli-sensitive low-molecular-weight gel with an aggregate-induced emission effect for sol-gel transition detection. ChemistryOpen, 2018, 7(6): 457–462

[22] Yu X, Chen H, Shi X, Albouy P A, Guo J, Hu J, Li M. Liquid crystal gelators with photo-responsive and AIE properties. Materials Chemistry Frontiers, 2018, 2(12): 2245–2253

[23] Shao L, Fan S, Meng Y, Gan Y, Shao W, Wang Z, Chen D, Ouyang G. Design, synthesis, biological activities and 3D-QSAR studies of quinazolinone derivatives containing hydrazone structural units. New Journal of Chemistry, 2021, 45(10): 4626–4631

[24] Paruch K, Popiołek Ł, Biernasiuk A, Berecka-Rycerz A, Malm A, Gumieniczek A, Wujec M. Novel derivatives of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid hydrazide: synthesis, lipophilicity, and in vitro antimicrobial activity screening. Applied Sciences, 2021, 11(3): 1180

[25] Jeong M J, Park J H, Lee C J, Chang J Y. Discotic liquid crystalline hydrazone compounds: synthesis and mesomorphic properties. Organic Letters, 2006, 8(11): 2221–2224

[26] Oliveira W, Mezalira D Z, Westphal E. Acylhydrazones liquid crystals: effect of structure over thermal behaviour and molecular switching. Liquid Crystals, 2020, 48(1): 88–99

[27] Sgobbi L F, Pinho V D, Cabral M F, Burtoloso A C B, Machado S A S. Hydrazone molecules as mimics for acetylcholinesterase. A new route towards disposable biosensors for pesticides? Sensors and Actuators. B, Chemical, 2013, 182: 211–216

[28] Bai A, Zhang Y, Tian J, Huang Y, Yang J. Novel acylhydrazone based chemosensor: “on-off” fluorescent and chromogenic detection of F⁻ and Fe³⁺ with high selectivity and sensitivity. Tetrahedron, 2022, 120: 132900

[29] Huang Y, Li H, Li Z, Zhang Y, Cao W, Wang L, Liu S. Unusual C–I···O halogen bonding in triazole derivatives: gelation solvents at two extremes of polarity and formation of superorganogels. Langmuir, 2017, 33(1): 311–321

[30] Yuan Y, Zhang R, Cheng X, Xu S, Liu B. A FRET probe with AIEgen as the energy quencher: dual signal turn-on for self-validated caspase detection. Chemical Science, 2016, 7(7): 4245–4250

[31] Xu G, Tang Y, Ma Y, Xu A, Lin W. A new aggregation-induced emission fluorescent probe for rapid detection of nitroreductase and its application in living cells. Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy, 2018, 188: 197–201

[32] Xu Y, Cao J, Li Q, Li J, He K, Shen T, Liu X, Yuan C, Zeng B, Dai L. Novel azobenzene-based amphiphilic copolymers: synthesis, self-assembly behavior and multiple-stimuli-responsive properties. RSC Advances, 2018, 8(29): 16103–16113

[33] Huang Y, Tu W, Yuan Y, Fan D. Novel organogelators based on pyrazine-2,5-dicarboxylic acid derivatives and their mesomorphic behaviors. Tetrahedron, 2014, 70(6): 1274–1282

[34] Sinnokrot M O, Valeev E F, Sherrill C D. Estimates of the ab initio limit for pi-pi interactions: the benzene dimer. Journal of the American Chemical Society, 2002, 124(36): 10887–10893

[35] Ray S, Das A. Studies on the π–π stacking features of imidazole units present in a series of 5-amino-1-alkylimidazole-4-carboxamides. Journal of Molecular Structure, 2015, 1089: 146–152

[36] Wang X, Cui W, Li B, Zhang X, Zhang Y, Huang Y. Supramolecular self-assembly of two-component systems comprising aromatic amides/Schiff base and tartaric acid. Frontiers of Chemical Science and Engineering, 2020, 14(6): 1112–1121

[37] Chow H, Wang G. Enhanced gelation property due to intra-molecular hydrogen bonding in a new series of bis(amino acid)-functionalized pyridine-2,6-dicarboxamide organogelators. Tetrahedron, 2007, 63(31): 7407–7418

[38] Zhang H, Tao F, Cui Y, Xu Z. The aggregation induced fluorescence effect enhanced by a reasonable length of carbon chain. Journal of Molecular Liquids, 2020, 302: 112550

[39] Wang H, Shen X, Ge J, Deng Y, Ding F, Wang Z, Zhu W, Hu L, He J, Gu X. Rational design of AIE-based carbazole derivatives for lipid droplet-specific imaging in living cells. Chemicke Zvesti, 2023, 77(1): 563–569

[40] Ge S, Li B, Meng X, Yan H, Yang M, Dong B, Lu Y. Aggregation-induced emission, multiple chromisms and self-organization of N-substituted-1,8-naphthalimides. Dyes and Pigments, 2018, 148: 147–153

[41] Shang H, Ding Z, Shen Y, Yang B, Liu M, Jiang S. Multi-color tunable circularly polarized luminescence in one single AIE system. Chemical Science, 2020, 11(8): 2169–2174

[42] Choi Y, Lee S S, Jung J H. Unusual fluorescence and sol-gel transition properties of a pyridine-based polymeric gel formed via the hydrazone reaction. Journal of Materials Chemistry. C, Materials for Optical and Electronic Devices, 2016, 4(41): 9646–9650

[43] Xu Y, Xue P, Xu D, Zhang X, Liu X, Zhou H, Jia J, Yang X, Wang F, Lu R. Multicolor fluorescent switches in gel systems controlled by alkoxyl chain and solvent. Organic & Biomolecular Chemistry, 2010, 8(19): 4289–4296

[44] Raju V, Kumar R S, Kumar S K A, Madhu G, Bothra S, Sahoo S K. A ninhydrin-thiosemicarbazone based highly selective and sensitive chromogenic sensor for Hg²⁺ and F⁻ ions. Journal of Chemical Sciences, 2020, 132(1): 89

[45] Panja S, Bhattacharya S, Ghosh K. Cholesterol-appended benzimidazolium salts: synthesis, aggregation, sensing, dye adsorption, and semiconducting properties. Langmuir, 2017, 33(33): 8277–8288

[46] Anand T, Sivaraman G, Iniya M, Siva A, Chellappa D. Aminobenzohydrazide based colorimetric and ‘turn-on’ fluorescence chemosensor for selective recognition of fluoride. Analytica Chimica Acta, 2015, 876: 1–8

[47] Liu Y, Li Z, Zhang H, Wang H, Li C. Colorimetric sensor and inverse fluorescent behavior of anions by calix[4]arene possessing imidazo[4,5-f]-1,10-phenanthroline groups and its Ru(II) complex. Supramolecular Chemistry, 2008, 20(4): 419–426

Competing interests

The authors declare that they have no competing interests.

Acknowledgements

This work was financially supported by the National Key Research and Development Program of China (Grant No. 2018YFA0903700)

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://doi.org/10.1007/s11705-023-2366-0 and is accessible for authorized users.

RIGHTS & PERMISSIONS

2023 Higher Education Press