Skip to main content
SpringerLink
Log in

Synthesis, characterization and ion recognition studies of lower rim 1,3-di{rhodamine} conjugate of calix[4]arene

  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

An amido-linked rhodamine conjugate of calix[4]arene, L has been synthesized and characterized. Metal ion recognition properties of L have been studied by emission and absorption techniques with 14 different metal ions including the transition ones. Results show that, L exhibits ratiometric emission intensity towards Hg2+, Fe2+, Fe3+, Cu2+, Pb2+ and Zn2+. Composition of the complex formed in the solution has been found to be 1:2 (L:Mn + ), based on the Job’s plot. The L can also act as a chemosensor for Hg2+ through naked eye detection. Fluorescence quenching observed at 485 nm follows an order, Hg2+ > > Fe3+ ~ Cu2+ > Zn2+ > Pb2+ > Ca2+, while the enhancement observed at 580 nm follows, Hg2+ > > Fe2+ ~ Pb2+ > Zn2+. Mode of interaction of Mn +  with L is by the ring opening of spirolactam moiety.

An amido-linked rhodamine conjugate of calix[4]arene, L has been synthesized and characterized and was shown to exhibit ratiometric emission towards Hg2+, Fe2+, Fe3+, Cu2+, Pb2+ and Zn2+. L can act as a chemosensor for Hg2+ by showing a colour change and by forming a 1:2 L:M n+ complex while opening the spirolactam moiety.

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

Scheme 1
Figure 1
Figure 2
Scheme 2
Figure 3
Figure 4
Figure 5
Figure 6
Figure 7
Figure 8
Figure 9

Similar content being viewed by others

References

  1. (a) Kubin R F and Fletcher A N 1982 J. Lumin. 27 455; (b) Kojima H, Hirotani M, Nakatsubo N, Kikuchi K, Urano Y, Higuchi T, Hirata Y and Nagano T 2001 Anal. Chem. 73 1967; (c) Chen X, Nam S–W, Jou M J, Kim Y, Sung-Jin Kim S–J, Park S and Yoon J 2008 Org. Lett. 10 5235; (d) Yang H, Zhou Z, Huang K, Yu M, Li F, Yi T and Huang C 2007 Org. Lett. 9 4729

  2. (a) Lohar S, Banerjee A, Sahana A, Banik A, Mukhopadhyay S K and Das D 2013 Anal. Methods 5 442; (b) Wang Z, Wu D, Wu G, Yang N and Wu A 2013 J. Hazard. Mater. 244 621; (c) Chen X, Pradhan T, Wang F, Kim J S and Yoon J 2012 Chem. Rev. 112 1910; (d) Jun M E and Ahn K H 2010 Org. Lett. 12 2790

  3. Shiraishi Y, Sumiya S, Kohno Y and Hirai T 2008 J. Org. Chem. 73 8571

    Article  CAS  Google Scholar 

  4. (a) Dujols V, Ford F and Czarnik A W 1997 J. Am. Chem. Soc. 119 7386; (b) Chen X, Jou M J, Lee H, Kou S, Lim J, Nam S-W, Park S, Kim K-M and Yoon J 2009 Sensors Actuators B 137 597

  5. Kwon J Y, Jang Y J, Lee Y J, Kim K M, Seo M S, Nam W and Yoon J 2005 J. Am. Chem. Soc. 127 10107

    Article  CAS  Google Scholar 

  6. (a) Othman A B, Lee J W, Wu J-S, Kim J S, Abidi R, Thuery P, Strub J M, Dorsselaer A V and Vicens J 2007 J. Org. Chem. 72 7634; (b) Lee Y H, Lee M H, Zhang J F and Kim J S 2010 J. Org. Chem. 75 7159

  7. Zheng X Y, Zhang W J, Mu L, Zeng X, Xue S F, Tao Z and Yamatob T 2010 J. Incl. Phenom. Macrocycl. Chem. 68 139

    Article  CAS  Google Scholar 

  8. Collins E M, McKervey M A, Madigan E, Moran M B, Owens M, Ferguson G and Harris S J 1991 J. Chem. Soc. Perkin Trans. 1 3137

    Article  Google Scholar 

  9. Soh J H, Swamy K M K, Kim S K, Kim S, Lee S-H and Yoon J 2007 Tetrahedron Lett. 48 5966

    Article  CAS  Google Scholar 

  10. (a) Kim H N, Lee M H, Kim H J, Kim J S and Yoon J 2008 Chem. Soc. Rev. 37 1465; (b) Li C-Y, Zhou Y, Li Y-F, Kong X–F, Zou C–X and Weng C 2013 Anal. Chim. Acta. 774 79

    Google Scholar 

  11. (a) Benesi H A and Hildebrand J H 1949 J. Am. Chem. Soc. 71 2703; (b) Mukhopadhyay M, Banerjee D, Koll A, Mandal A, Filarowski A, Fitzmaurice D, Das R and Mukherjee S 2005 J. Photochem. Photobiol. A: Chem. 125 94

    Google Scholar 

Download references

Acknowledgements

CPR gratefully acknowledges the financial support from the Department of Science and Technology (DST), the Council of Scientific and Industrial Research (CSIR), New Delhi and Department of Atomic Energy (DAE) Board of Research in Nuclear Sciences (BRNS). JPC gratefully acknowledges CSIR for his research fellowships. JD gratefully acknowledges Defense Research and Development Laboratory (DRDL) for allowing him to register for Ph.D. programme at Indian Institute of Technology Bombay. We thank Dr. J K Khedkar for extending help during the revision process.

Author information

Authors and Affiliations

  1. Bioinorganic Laboratory, Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076, India

    JUGUN PRAKASH CHINTA, JAYARAMAN DESSINGOU & CHEBROLU PULLA RAO

Authors
  1. JUGUN PRAKASH CHINTA
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. JAYARAMAN DESSINGOU
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. CHEBROLU PULLA RAO
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to CHEBROLU PULLA RAO.

Rights and permissions

Reprints and permissions

About this article

Cite this article

CHINTA, J.P., DESSINGOU, J. & RAO, C.P. Synthesis, characterization and ion recognition studies of lower rim 1,3-di{rhodamine} conjugate of calix[4]arene. J Chem Sci 125, 1455–1461 (2013). https://doi.org/10.1007/s12039-013-0500-0

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-013-0500-0

Keywords

Search

Navigation