Skip to main content
SpringerLink
Log in

Terthiophene-functionalized mesoporous silica-based fluorescence sensor for the detection of trace methyl orange in aqueous media

  • Original Paper
  • Published:
Microchimica Acta Aims and scope Submit manuscript

Abstract

A terthiophene-functionalized mesoporous SBA-15 silica, i.e., TTU-SBA-15, was successfully developed and used as a highly selective and ultrasensitive fluorescence sensor for methyl orange (MO) detection. When the concentration of MO was increased, the fluorescence emission intensity of TTU-SBA-15 suspensions at 452 nm gradually decreased at an excitation wavelength of 368 nm, and the color of the suspension solutions changed obviously from blue to dark under 365 nm UV light. The fluorescence intensity at 452 nm was linearly proportional to the concentration of MO in the range 0.20 − 2.0 μM, with a detection limit of 0.092 μM. Competitive pollutants, variations in pH, and sample recycling had subtle or negligible effects on the detection of MO. TTU-SBA-15 was applied to the determination of MO in tap water, and recoveries from spiked samples were in the range 98.3 − 103.0%. This study provides a convenient and effective strategy to realize highly sensitive and selective sensors that could target dyes via the functional modification of mesoporous materials.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 1

Similar content being viewed by others

References

  1. Abdi J, Vossoughi M, Mahmoodi NM, Alemzadeh I (2017) Synthesis of amine-modified zeolitic imidazolate framework-8, ultrasound-assisted dye removal and modeling. Ultrason Sonochem 39:550–564

    Article  CAS  PubMed  Google Scholar 

  2. Li X, Wang Y, Zhang P, Ge W (2021) Highly sensitivity, selectivity chemosensor for methyl orange using upconversion NaBiF4: Yb/Tm nanosheets. J Solid State Chem 301:12230

    Article  Google Scholar 

  3. Sun HM, Ju CG, Zhao YW, Wang CY, Wu Y (2020) Preparation of SiO2@ZIF-67/CNTs and research on its adsorption performance at low-temperature. Colloid Surface A 603:125205

    Article  CAS  Google Scholar 

  4. Derami HG, Gupta P, Gupta R, Rathi P, Morrissey JJ, Singamaneni S (2020) Palladium nanoparticle-decorated mesoporous polydopamine/bacterial nanocellulose as a catalytically active universal dye removal ultrafiltration membrane. ACS Appl Nano Mater 3:5437–5448

    Article  Google Scholar 

  5. Sena S, Demirer GN (2003) Anaerobic treatment of real textile wastewater with a fluidized bed reactor. Water Res 37:1868–1878

    Article  Google Scholar 

  6. Hassanzadeh-Tabrizi SA, Motlagh MM, Salahshour S (2016) Synthesis of ZnO/CuO nanocomposite immobilized on c-Al2O3 and application for removal of methyl orange. Appl Surf Sci 384:237–243

    Article  CAS  Google Scholar 

  7. Ranjith KS, Manivel P, Rajendrakumar RT, Uyar T (2017) Multifunctional ZnO nanorod-reduced graphene oxide hybrids nanocomposites for effective water remediation: effective sunlight driven degradation of organic dyes and rapid heavy metal adsorption. Chem Eng J 325:588–600

    Article  CAS  Google Scholar 

  8. Parmar B, Bisht KK, Rajput G, Suresh E (2021) Recent advances in metal–organic frameworks as adsorbent materials for hazardous dye molecules. Dalton Trans 50:3083–3108

    Article  CAS  PubMed  Google Scholar 

  9. Shan Z, Lu MS, Curry DE, Beale S (2017) Regenerative nanobots based on magnetic layered double hydroxide for azo dye removal and degradation. Chem Commun 53:10456–10458

    Article  CAS  Google Scholar 

  10. Meng S, Yu S, Tang F, Hu X, Lu J, Fei X, Zhu M (2021) Fiber engineering of silica-based aerogels with surface specificity and regenerability for continuous removal of dye pollutants from wastewaters. Microporous Mesoporous Mater 314:110874

    Article  CAS  Google Scholar 

  11. Majee BP, Srivastava V, Mishra AK (2020) Surface-enhanced Raman scattering detection based on an interconnected network of vertically oriented semiconducting few-layer MoS2 Nanosheets. ACS Appl Nano Mater 3(5):4851–4858

    Article  CAS  Google Scholar 

  12. Nguyen TV, Vu DC, Pham VH, Bui H (2021) Improvement of SERS for detection of ultra-low concentration of methyl orange by nanostructured silicon decorated with Ag nanoparticles. Optik 231:166431

    Article  CAS  Google Scholar 

  13. Fang GZ, Wu Y, Dong XM (2013) Simultaneous determination of banned acid orange dyes and basic orange dyes in foodstuffs by liquid chromatography-tandem electrospray ionization mass spectrometry via negative/positive ion switching mode. J Agric Food Chem 61:3834–3841

    Article  CAS  PubMed  Google Scholar 

  14. Witkowski B, Ganeczko M, Biesaga M (2017) Identification of orcein and selected natural dyes in 14th and 15th century liturgical paraments with high-performance liquid chromatography coupled to the electrospray ionization tandem mass spectrometry (HPLC-ESI/MS/MS). Microchem J 133:370–379

    Article  CAS  Google Scholar 

  15. Tropp J, Ihde MH, Azoulay JD (2020) A sensor array for the nanomolar detection of azo dyes in water. ACS Sen 5:1541–1547

    Article  CAS  Google Scholar 

  16. Liu TH, Ding LP, Zhao KR (2012) Single-layer assembly of pyrene end-capped terthiophene and its sensing performances to nitroaromatic explosives. J Mater Chem 22:1069–1077

    Article  CAS  Google Scholar 

  17. Wu M, Sun LJ, Miao KS, Wu YZ, Fan LJ (2018) Detection of Sudan dyes based on inner-filter effect with reusable conjugated polymer fibrous membranes. ACS Appl Mater Interfaces 10:8287–8295

    Article  CAS  PubMed  Google Scholar 

  18. Wang J, Liu HB, Tong Z, Ha CS (2015) Fluorescent/luminescent detection of natural amino acids by organometallic systems. Coord Chem Rev 303:139–184

    Article  CAS  Google Scholar 

  19. Hu Y, Gao Z (2020) Sensitive detection of Sudan dyes using tire-derived carbon dots as a fluorescent sensor. Spectrochim Acta A Mol Biomol Spectrosc 239:118514

    Article  CAS  PubMed  Google Scholar 

  20. Fang AJ, Long Q, Zhang Y (2016) Upconversion nanosensor for sensitive fluorescence detection of Sudan I-IV based on inner filter effect. Talanta 148:129–134

    Article  CAS  PubMed  Google Scholar 

  21. Ye XL, Zhang J, Chen H, Huang F (2014) Fluorescent nanomicelles for selective detection of Sudan dye in Pluronic F127 aqueous media. ACS Appl Mater Interfaces 6(7):5113–5121

    Article  CAS  PubMed  Google Scholar 

  22. Bogireddy NKR, Lara J, Fragoso LR, Agarwal V (2020) One-step hydrothermal preparation of highly stable N doped oxidized carbon dots for toxic organic pollutants sensing and bioimaging. Chem Eng J 401:126097

    Article  CAS  Google Scholar 

  23. Zhao DY, Feng JL, Huo QS (1998) Copolymer syntheses of mesoporous silica with periodic 50 to 300 angstrom pores. Science 279:548–552

    Article  CAS  PubMed  Google Scholar 

  24. Kim H, Rao BA, Jeong J, Angupillai S, Choi JS, Nam JO, Lee CS, Sona YA (2016) A rhodamine scaffold immobilized onto mesoporous silica as a fluorescent probe for the detection of Fe (III) and applications in bio-imaging and microfluidic chips. Sens Actuators B Chem 224:404–412

    Article  CAS  Google Scholar 

  25. Paul L, Mukherjee S, Chatterjee S, Bhaumik A (2019) Organically functionalized mesoporous SBA-15 type material bearing fluorescent sites for selective detection of HgII from aqueous medium. ACS Omega 4:17857–17863

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. Liu HB, Liang YH, Liang J (2020) Pyrene derivative-functionalized mesoporous silica–Cu2+ hybrid ensemble for fluorescence “turn-on” detection of H2S and logic gate application in aqueous media. Anal Bioanal Chem 412:905–913

    Article  CAS  PubMed  Google Scholar 

  27. Wan XJ, Yao S, Liu HY, Yao YW (2013) Selective fluorescence sensing of Hg2+ and Zn2+ ions through dual independent channels based on the site-specific functionalization of mesoporous silica nanoparticles. J Mater Chem A 1:10505–10512

    Article  CAS  Google Scholar 

  28. Dong ZP, Tian X, Chen YZ, Hou JR, Ma JT (2013) Rhodamine group modified SBA-15 fluorescent sensor for highly selective detection of Hg2+ and its application as an INHIBIT logic device. RSC Adv 3:2227–2233

    Article  CAS  Google Scholar 

  29. Zarabadi-Poor P, Badiei A, Yousefi AA, Barroso-Flores J (2013) Selective optical sensing of Hg (II) in aqueous media by H-acid/SBA-15: a combined experimental and theoretical study. J Phys Chem C 117:9281–9289

    Article  CAS  Google Scholar 

  30. Gao M, Zeng J, Liang K, Zhao D, Kong B (2020) Interfacial assembly of mesoporous silica based optical heterostructures for sensing applications. Adv Funct Mater 30:1906950

    Article  CAS  Google Scholar 

  31. Enshirah D (2017) Adsorption of heavy metals on functionalized-mesoporous silica: a review. Microporous Mesoporous Mater 247:145–157

    Article  Google Scholar 

  32. Wang J, Zhang X, Liu HB, Zhang D, Nong H, Wu P, Chen P, Li D (2020) Aggregation induced emission active fluorescent sensor for the sensitive detection of Hg2+ based on organic–inorganic hybrid mesoporous material. Spectrochim Acta A Mol Biomol Spectrosc 227:117585

    Article  CAS  PubMed  Google Scholar 

  33. Zhao LY, Li JY, Sui D, Wang Y (2017) Highly selective fluorescence chemosensors based on functionalized SBA-15 for detection of Ag+ in aqueous media. Sens Actuators B Chem 242:1043–1049

    Article  CAS  Google Scholar 

  34. Pal P, Rastogi SK, Gibson CM, Aston DE, Branen AL, Bitterwolf TE (2011) Fluorescence sensing of zinc(II) using ordered mesoporous silica material (MCM-41) functionalized with N-(quinolin-8-yl)-2-[3-(triethoxysilyl)pro-pylamino]acetamide. ACS Appl Mater Interfaces 3:279–286

    Article  CAS  PubMed  Google Scholar 

  35. Gao ZP, Qiao M, Tan MM, Peng HN, Ding LP (2020) Surface functionalization of mesoporous silica nanoparticles with pyronine derivative for selective detection of hydrogen sulfide in aqueous solution. Colloids Surf A 586:124194

    Article  CAS  Google Scholar 

  36. Huang J, Liu HB, Wang J (2021) Functionalized mesoporous silica as a fluorescence sensor for selective detection of Hg2+ in aqueous medium. Spectrochim Acta A Mol Biomol Spectrosc 246:118974

    Article  CAS  PubMed  Google Scholar 

  37. Lashgaria N, Badieia A, Ziarani GM (2017) A novel functionalized nanoporous SBA-15 as a selective fluorescent sensor for the detection of multianalytes (Fe3+ and Cr2O72−) in water. J Phys Chem Solids 103:238–248

    Article  Google Scholar 

  38. Wu HM, Xiao Y, Guo Y (2020) Functionalization of SBA-15 mesoporous materials with 2-acetylthiophene for adsorption of Cr(III) ions. Microporous Mesoporous Mater 292:109754

    Article  CAS  Google Scholar 

  39. Timin AS, Rumyantsev EV, Solomonov AV, Musabirov II, Sergeev SN, Ivanov SP, Berlier G, Balantseva E (2015) Preparation and characterization of organo-functionalized silicas for bilirubin removal. Colloids and Surfaces A: Physicochem Eng Aspects 464:65–77

    Article  CAS  Google Scholar 

  40. Wang C, Li QL, Wang B (2018) Fluorescent sensors based on AIEgenfunctionalised mesoporous silica nanoparticles for the detection of explosives and antibiotics. Inorg Chem Front 5:2183

    Article  CAS  Google Scholar 

  41. Ma C, Li P, Xia L, Qu F, Kong RM, Song ZL (2021) A novel ratiometric fluorescence nanoprobe for sensitive determination of uric acid based on CD@ZIF-CuNC nanocomposites. Microchim Acta 188:259

    Article  CAS  Google Scholar 

  42. Pyo K, Thanthirige VD, Kwak K, Pandurangan P, Ramakrishna G, Lee D (2015) Ultrabright luminescence from gold nanoclusters: rigidifying the Au(I)-thiolate shell. J Am Chem Soc 137(25):8244–8250

    Article  CAS  PubMed  Google Scholar 

  43. Wang J, Ma Q, Wang Y, Li Z, Li Z, Yuan Q (2018) New insights into the structure–performance relationships of mesoporous materials in analytical science. Chem Soc Rev 47:8766–8803

    Article  CAS  PubMed  Google Scholar 

Download references

Funding

This work was supported by the National Natural Science Foundation of China (NSFC) (Grant Nos. 21966006) and Natural Science Foundation of Guangxi Province (Grant No. 2018GXNSFAA050015).

Author information

Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Guangxi University, Nanning, 530004, People’s Republic of China

    Jing Huang, Jing Wang, Dong Li, Pengxiang Chen & Hai-Bo Liu

  2. Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, Guangxi University, Nanning, 530004, People’s Republic of China

    Jing Wang

Authors
  1. Jing Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jing Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Dong Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Pengxiang Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Hai-Bo Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Jing Wang or Hai-Bo Liu.

Ethics declarations

Conflict of interest

The authors declare no competing interests.

Additional information

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 15979 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Huang, J., Wang, J., Li, D. et al. Terthiophene-functionalized mesoporous silica-based fluorescence sensor for the detection of trace methyl orange in aqueous media. Microchim Acta 188, 410 (2021). https://doi.org/10.1007/s00604-021-05063-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00604-021-05063-x

Keywords

Search

Navigation