SpringerLink
Log in

Synthesis and Evaluation of a Schiff-Based Fluorescent Chemosensors for the Selective and Sensitive Detection of Cu2+ in Aqueous Media with Fluorescence Off-On Responses

  • ORIGINAL ARTICLE
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

Copper being an essential nutrient; also pose a risk for human health in excessive amount. A simple and convenient method for the detection of trace amount of copper was employed using an optical probe R1 based on Schiff base. The probe was synthesized by Schiff base condensation of benzyl amine and 2-hydroxy-1-napthaldehyde and characterized by single X-ray diffraction, 1H NMR and FTIR. By screening its fluorescence response in a mixture of DMSO and H2O (20:80, v/v) R1 displayed a pronounced enhancement in fluorescence only upon treatment with copper. Other examined metal ions such as alkali, alkaline and transition had no influence. Within a wide pH range 5–12 R1 could selectively detect copper by interrupting ICT mechanism that results in CHEF. From Job’s plot analysis a 2:1 binding stoichiometry was revealed. The fluorescence response was linear in the range 1–10 × 10−9 M with detection limit 30 × 10−9 M. Association constant was determined as 1 × 1011 M−2 by Benesi-Hilderbrand plot. As a fast responsive probe it possesses good reproducibility and was employed for detection of copper in different water samples.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14
Fig. 15
Fig. 16
Fig. 17

Similar content being viewed by others

References

  1. Ivo G, Jean-Marc C, Valmadimir B (2004) New green fluorescent polyvinylcarbazole copolymer with 1,8-naphthalimide side chains as chemosensor for iron cations. Polym Adv Technol 15:382–386

    Article  Google Scholar 

  2. Zhanxian L, Lifeng Z, **aoya L, Yonghai N, Jianhong C, Liube W, Mingming Y (2012) A fluorescent color/intensity changed chemosensor for Fe3+ by photo induced electron transfer (PET) inhibition of fluoranthene derivative. Dyes Pigments 94:60–65

    Article  Google Scholar 

  3. Mani V, Shu-Pao W (2012) A BODIPY-based colorimetric and fluorometric chemosensor for Hg (II) ions and its application to living cell imaging. Org Biomol Chem 10:5410–5416

    Article  Google Scholar 

  4. Li J, Ling W, Bo Z, Rui-Yong W, Gui Y (2011) A fluorescence turn-on Hg2+ probe based on rhodamine with excellent sensitivity and selectivity in living cells. Open J Inorg Chem 1:16–22

    Article  CAS  Google Scholar 

  5. Ghandhi S, Thangaraj A, Durajsamy C (2012) Development of a pyrene based “turn on” fluorescent chemosensor for Hg2+. RSC Adv 2:10605–10609

    Article  Google Scholar 

  6. Qianni G, Qingbin Z, **aoxiao Z, **n Z (2014) Highly sensitive detection of mercury (II) in aqueous media by tetraphenylporphyrin with a metal ion receptor. Supramol Chem 26:836–842

    Article  Google Scholar 

  7. Arunabha T, Dipendu M, Pranab D, Bijan M, Sundargopal G (2014) Synthesis of triazole linked fluorescent amino acid and carbohydrate bio-conjugates: a highly sensitive and skeleton selective multi-responsive chemosensor for Cu (II) and Pb (II)/Hg (II) ions. RSC Adv 4:1918–1928

    Article  Google Scholar 

  8. Keyur DB, Hrishikesh SG, Bharat AM, Disha JV, Debdeep M, Vinod KJ (2012) Calix receptor edifice; scrupulous turn off fluorescent sensor for Fe (III), Co (II) and Cu (II). J Fluoresc 22:1493–1500

    Article  Google Scholar 

  9. Shi-Rong L, Shu-Pao W (2011) An NBD-based sensitive and selective fluorescent sensor for copper (II) ion. J Fluoresc 21:1599–1605

    Article  Google Scholar 

  10. Zhihong X, Like Z, Rui G, Tiancheng X, Chanzeng W, Zhi Z, Fengling Y (2011) A highly sensitive and selective colorimetric and off–on fluorescent chemosensor for Cu2+ based on rhodamine B derivative. Sensors Actuators B Chem 156:546–552

    Article  Google Scholar 

  11. Muhammad S, Ki-Hwan L (2014) Selective fluorescence detection of Cu2+ in aqueous solution and living cells. J Lumin 145:843–848

    Article  Google Scholar 

  12. Rakesh KM, Pallavi S (2007) Novel copper (II)-selective electrode based on 2,2′: 5′,2″-terthiophene in PVC matrix. Int J Electrochem Sci 2:832–847

    Google Scholar 

  13. Najua DT, Luqman AC, Zwani Z, Suraya AR (2008) Adsorption of copper from aqueous solutions by elais guineensis kernel activated carbon. J Eng Sci Technol 3:180–189

    Google Scholar 

  14. Aeju L, Jungwook C, Ok PK, Hyun** C, ** WK, Soo-Young Y, Kyeongsoon P (2013) A novel near-infrared fluorescence chemosensor for copper ion detection using click ligation and energy transfer. Chem Commun 49:5969–5971

    Article  Google Scholar 

  15. Yeong KJ, Chang UN, Ha LK, In HH, Cheal K (2013) A Selective colorimetric and fluorescent chemosensor based-on naphthol for detection of Al3+ and Cu2+. Dyes Pigments 99:6–13

    Article  Google Scholar 

  16. Cesar GF (2005) Relevance, essentiality and toxicity of trace elements in human health. Mol Asp Med 26:235–244

    Article  Google Scholar 

  17. Selvaraj R, Younghun K, Cheol KJ, Jongheop Y (2004) Removal of copper from aqueous solutions by aminated and protonated mesoporous aluminas: kinetics and equilibrium. J Colloid Interface Sci 273:14–21

    Article  Google Scholar 

  18. Pragnesh ND, Subrahmanyam N, Surendra S (2009) Kinetics and thermodynamics of copper ions removal from aqueous solution by use of activated charcoal. Indian J chem Technol 16:234–239

    Google Scholar 

  19. Chen Z, Yan S, Ning X, Yapeng L, Jiayuan X (2014) A novel highly sensitive and selective fluorescent sensor for imaging copper (II) in living cells. J Fluoresc 24:1331–1336

    Article  Google Scholar 

  20. Hsuan-Fu W, Shu-Pao W (2013) A Pyrene-based highly selective turn-on fluorescent sensor for copper (II) ions and its application in living cell imaging. Sensors Actuators B 181:743–748

    Article  Google Scholar 

  21. Tae GJ, Yu JN, Jae JL, Myoung ML, Sun YL, Cheal K (2015) A diaminomaleonitrile based selective colorimetric chemosensor for copper (II) and fluoride ions. New J Chem 39:2580–2587

    Article  Google Scholar 

  22. Juanmei Z, Li Z, Wen**g L, Dozhong S, Rilong Z, Dawei P (2011) Determination of trace copper in water samples by anodic strip** voltammetry at gold microelectrode. Int J Electrochem Sci 6:4690–4699

    Google Scholar 

  23. Jafer Ahmad A, Shajudha Begum A (2012) Adsorption of copper from aqueous solution by low cost adsorbent. Arch Appl Sci Res 4:1532–1539

    Google Scholar 

  24. Seul AL, Jae JL, Jong WS, Kil SM, Cheal K (2015) A colorimetric chemosensor for the sequential detection of copper (II) and cysteine. Dyes Pigments 116:131–138

    Article  Google Scholar 

  25. I-Ting H, Jean-Ho C, Wen-Sheng C (2011) Calix[4] arene with lower-rim β-amino α,β-unsaturated ketones containing bis-chelating sites as a highly selective fluorescence turn-On chemosensor for two copper (II) ions. Eur J Org Chem 2011:1472–1481

    Article  Google Scholar 

  26. Shu-Pao W, Zhen-Ming H, Shi-Rong L, Peter KC (2012) A pyrene-based highly selective turn-on fluorescent sensor for copper (II) ion and its application in live cell imaging. J Fluoresc 22:253–259

    Article  Google Scholar 

  27. Manoj K, Nagendra B, Vandana B (2010) Fluorescent chemosensor for Cu2+ ion based on iminoanthryl appended calix[4]arene. J Incl Phenom Macrocycl Chem 66:139–145

    Article  Google Scholar 

  28. Muthaiah S, Yen-Hsing W, Ashutosh S, Mandapati VRR, Hong-Cheu L (2013) Novel pyrene- and anthracene-based Schiff base derivatives as Cu2+ and Fe3+ fluorescence turn-on sensors and for aggregation induced emissions. J Mater Chem A 1:1310–1318

    Article  Google Scholar 

  29. Nur A, Emu H, Ibrahim Y, Alaaddin C (2009) A highly sensitive and selective fluorescent sensor for the determination of copper (II) based on a schiff base. Dyes Pigments 83:211–217

    Article  Google Scholar 

  30. Aixiang D, Fang T, Tao W, Xutang T, Jiaxizng Y (2015) A α-cyanostilbene-modified Schiff base as efficient turn-on fluorescent chemosensor for Zn2+. J Chem Sci 127:375–382

    Article  Google Scholar 

  31. Dehua Z, **aoyan Z (2013) Crystallization and characterization of a new fluorescent molecule based on Schiff base. JCPT 3:28–30

    Article  Google Scholar 

  32. Lei L, Yong-Qiang D, Hong-Wei L, Wa B, Yuqing W (2010) Fluorescent chemosensor based on Schiff base for selective detection of zinc (II) in aqueous solution. Tetrahedron Lett 51:618–621

    Article  Google Scholar 

  33. Supriti S, Titas M, Basab C, Anuradha M, Anupam B, Jaromir M, Pabitra C (2012) A water soluble Al3+ selective colorimetric and fluorescent turn-on chemosensor and its application in living cell imaging. Analyst 137:3975–3981

    Article  Google Scholar 

  34. Mohamed NI, Salah EAS (2007) Synthesis, characterization and use of Schiff bases as fluorimetric analytical reagents. E-J Chem 4:531–535

    Article  Google Scholar 

  35. Vinod KG, Ashok KS, Lokesh KK (2014) A turn-on fluorescent chemosensor for Zn2+ions based on antipyrine schiff base. Sensors Actuators B Chem 204:507–514

    Article  Google Scholar 

  36. Reza A, Tayebe A, Hassan K, Majid R (2013) A new asymmetric Schiff base system as fluorescent chemosensor for Al3+ ion. Inorg Chem Commun 33:63–67

    Article  Google Scholar 

  37. Xavier A, Srividhya N (2014) Synthesis and study of Schiff base ligand. IOSR-J Appl Chem 17:6–15

    Article  Google Scholar 

  38. Vinod KG, Sudhir KS, Lokesh KK, Ajay KJ (2015) A highly selective colorimetric and turn-on fluorescent chemosensor based on 1-(2-pyridylazo)-2-naphthol for the detection of aluminium (III) ions. Sensors Actuators B Chem 209:15–24

    Article  Google Scholar 

  39. Sheldrick GM (2008) A short history of SHELXL. Acta Crystallogr A 64:112–122

    Article  CAS  Google Scholar 

  40. Westrip SP (2010) PublCIF: software for editing, validating and formatting crystallographic information files. J Appl Crystallogr 43:920–925

    Article  CAS  Google Scholar 

  41. Zhiyuan Z, Chunming S, Aifeng L, Zhenyu Z, Dongmei Z (2015) Highly selective detection of Cr (VI) in water matrix by a simple 1,8-Naphthalimide-based turn-on fluorescent sensor. J Fluoresc 25:335–340

    Article  Google Scholar 

  42. Olimpo G-B, Bruce KC, Claudio P, Natalia M, Marco TN, Natalia PM, Paulina P, Margarita EA (2014) Coumarin-based fluorescent probes for dual recognition of copper (II) and iron (III) ions and their application in bio-imaging. Sensors 14:1358–1371

    Article  Google Scholar 

  43. Hyo SJ, Pil SK, Jeong WL, Jae IK, Chang SH, Jong WK, Shihai Y, ** YL, Jung HL, Taiha J, Jong SK (2009) Coumarin-derived Cu2+-selective fluorescence sensor: synthesis, mechanisms, and applications in living cells. J Am Chem Soc 131:2008–2012

    Article  Google Scholar 

  44. Chunwei Y, Lingxin C, Jun Z, **hua L, ** L, Wenhai W, Bing Y (2011) “Off-On” based fluorescent chemosensor for Cu2+ in aqueous media and living cells. Talanta 85:1627–1633

    Article  Google Scholar 

  45. Yan-Qin W, Ying-Lai T, Fan Y, Yong-Rui Z, Bao-Hui Y (2007) A new selective fluorescent chemosensor for Cu (II) ion based on zinc porphyrin-dipyridylamino. Inorg Chem Commun 10:443–446

    Article  Google Scholar 

  46. Jiun-Ting Y, Wei-Chieh C, Shi-Rong L, Shu-Pao W (2014) A coumarin-based sensitive and selective fluorescent sensor for copper (II) ions. New J Chem 38:4434–4439

    Article  Google Scholar 

  47. Shu-Pao W, Tzu-Hao W, Shi-Rong L (2010) A highly selective turn-on fluorescent chemosensor for copper (II) ion. Tetrahedron 66:9655–9658

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Malakand, Chakdara, Lower Dir, KPK, Pakistan

    Maria Sadia, Robina Naz, Jehangir Khan & Rizwan Khan

Authors
  1. Maria Sadia
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Robina Naz
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jehangir Khan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Rizwan Khan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Maria Sadia.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sadia, M., Naz, R., Khan, J. et al. Synthesis and Evaluation of a Schiff-Based Fluorescent Chemosensors for the Selective and Sensitive Detection of Cu2+ in Aqueous Media with Fluorescence Off-On Responses. J Fluoresc 28, 1281–1294 (2018). https://doi.org/10.1007/s10895-018-2278-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-018-2278-4

Keywords

Search

Navigation