Skip to main content
Log in

Highly Selective Sensing of Li+ in H2O/CH3CN via Fluorescence ‘Turn-on’ Response of a Coumarin-Indole Linked Dyad: an Experimental and Theoretical Study

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

Abstract

A coumarin-indole dyad, N-((7-hydroxy-2-oxo-2H-chromen-4-yl)methyl)-1H-indole-2-carboxamide has been synthesized and characterized by 1H-NMR and 13C-NMR. Effect of various metal ions on fluorescent behavior was also studied. The synthesized compound showed remarkable specificity towards Li+ in organo-aqueous medium over other metal ions. Coordination of the compound with Li+ induces a turn-on fluorescence response. The sensor exhibited good binding constant and low detection limit towards Li+. Experimental results have been verified with Density Functional Theory and Time Dependent Density Functional Theory calculations.

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

Access this article

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

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11

Similar content being viewed by others

References

  1. Bissel RA, de Silva AP, Gunaratne HQN, Lynch PLM, Maguire GEM, Sandanayake KRAS (1992) Chem Soc Rev 21:187–195.

  2. de Silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, McCoy CP, Rademacher JT, Rice TE (1997) Chem Rev 97:1515–1566.

  3. Desvergne JP, Czarnik AW (1997) Fluorescent Chemosensors for Ion, Molecule Recognition; Eds. Kluwer Academic Publishers, Dordrecht, The Nederlands

    Book  Google Scholar 

  4. Prodi L, Bolletta F, Montalti M, Zaccheroni N (2000) Coord Chem Rev 205:59–83

  5. Valeur B, Leray I (2000) Coord Chem Rev 205:3–40

  6. de Silva AP, Fox DB, Huxley AJM, Moody TS (2000) Coord Chem Rev 205:41–57

  7. Bach RO (1985) Lithium-Current Applications in Science, Medicine and Technology. Wiley-Interscience, New York

    Google Scholar 

  8. Aurbach DJ (2000) Power Sources 89:206–218

    Article  CAS  Google Scholar 

  9. Lantelme F, Groult H, Kumagni N (2000) Electrochem. Acta 45:3171–3178

    CAS  Google Scholar 

  10. W. H. Meyer (1998) Adv Mater 10: 439–448.

  11. Yin J, Hua Y, Yoon J (2015) Chem Soc Rev 44:4619–4644.

  12. Jope RS (1999) Mol Psychiatry 4:117–128.

  13. Manji HK, Potter WZ, Lenox RH (1995) Arch Gen Psychiatry 52:531–543.

  14. Gupta VK, Jain AK, Maheshwari G (2007) Talanta 72:1469–1473

    Article  CAS  PubMed  Google Scholar 

  15. Gupta VK, Goyal RN, Jain AK, Sharma RA (2009) Electrochim Acta 54:3218–3224.

  16. Gupta VK, Singh AK, Ganjali MR, Norouzi P, Faridbod F, Mergu N (2013) Sens. Actuators B Chem 182:642–651

    Article  CAS  Google Scholar 

  17. Chen S, Fang YM, Xiao Q, Li J, Li SB, Chen HJ, Sun JJ, Yang HH (2012) Analyst 137:2021–2023

    Article  CAS  PubMed  Google Scholar 

  18. Mohadesi A, Taher MA (2007) Talanta 72:95–100

    Article  CAS  PubMed  Google Scholar 

  19. Mashhadizadeh MH, Pesteh M, Talakesh M, Sheikhshoaie I, Ardakani MM, Karimi MA (2008) Spectrochim Acta B 63:885–888.

  20. Cassella RJ, Magalhaes OIB, Couto MT, Lima ELS, Neves MAFS, Coutinho FMB (2005) Talanta 67:121–128

    Article  CAS  PubMed  Google Scholar 

  21. Ali A, Shen H, Yin X (1998) Anal Chim Acta 369:215–223.

  22. Ferreira SLC, Queiroz AS, Fernandes MS, dos Santos HC (2002) Spectrochim. Acta B 57:1939–1950

    Google Scholar 

  23. Li YP, Ming X, Zhang YH, Chang Z (2013) Inorg Chem Commun 33:6–9.

  24. Chen CH, Liao DJ, Wan CF, Wu AT (2013) Analyst 138:2527–2530

    Article  CAS  PubMed  Google Scholar 

  25. Gupta VK, Singh AK, Mergu N (2014) Electrochim Acta 117:405–412.

  26. Gupta VK, Singh AK, Kumawat LK (2014) Sens. Actuators B Chem. 195:98–108

    Article  CAS  Google Scholar 

  27. Gupta VK, Mergu N, Singh AK (2014) Sens. Actuators B Chem. 202:674–682

    Article  CAS  Google Scholar 

  28. Gupta VK, Mergu N, Kumawat LK, Singh AK (2015) Sens. Actuators B Chem. 207:216–223

    Article  CAS  Google Scholar 

  29. Kim KB, You DM, Jeon JH, Yeon YH, Kim JH, Kim C (2014) Tetrahedron Lett 55:1347–1352.

  30. Azadbakht R, Khanabadi J (2013) Tetrahedron 69:3206–3211

    Article  CAS  Google Scholar 

  31. Chaoxia G, Xiaofeng Y, Xiangyong W, Meishan P, Guangyou Z (2013) New J Chem 37:4163–4169.

  32. Zhou D, Sun C, Chen C, Cui X, Li W (2015) J Mol Struct 1079:315–320.

  33. Su Z, Chen K, Guo Y, Qi H, Yang X, Zhao M (2010) J Fluoresc 20:851–856.

  34. Ma Q, Zhang X, Zhao X, Jin Z, Mao G, Shen G, Yu R (2010) Anal Chim Acta 663:85–90.

  35. Chattopadhyay N, Mallick A, Sengupta S (2006) J Photochem Photobiol A 177:55–60

    Article  CAS  Google Scholar 

  36. Hyo SJ, Ji HH, Zee HK, Chul HK, Jong SK (2011) Org Lett 13:5056–5059.

  37. Kirubaharan CJ, Kalpana D, Lee YS (2012) Ind Eng Chem Res 51:7441–7446.

  38. Joshi S, Kumari S, Bhattacharjee R, Sarmah A, Sakhuja R, Pant DD (2015) Sens. Actuators B Chem. 220:1266–1278

    Article  CAS  Google Scholar 

  39. Ciampolini M, Nardi N, Valtancoli B, Micheloni M (1992) Coord Chem Rev 120:223–236.

  40. Kobiro K (1995) Coord Chem Rev 148:135–149

  41. Formica M, Fusi V, Micheloni M, Pontellini R, Romani P (1999) Coord Chem Rev 184:347–363.

  42. Cimpolini M, Formica M, Fusi V, Saint-Mauricec A, Micheloni M, Nardi N, Pontellini RR, Pina F, Romani P, Sabatini AM, Valtoncoli B (1999) Eur J Inorg Chem 1999:2261–2268

    Article  Google Scholar 

  43. Obare SO, Murphy CJ (2001) Inorg Chem 40:6080–6082.

  44. Gunnlaugsson T, Bichell B, Nolan C (2002) Tetrahedron Lett 43:4989–4992.

  45. Benco JS, Nienaber HA, McGimpsey WG (2004) J. Photochem. Photobiol. A 162:289–296

    Article  CAS  Google Scholar 

  46. King SH, Han SK, Park SH, Yoon CM, Keum SR (1999) Dyes Pigments 43:21–25

    Article  Google Scholar 

  47. Gunnlaugsson T, Bichell B, Nolan C (2004) Tetrahedron 60:5799–5806

    Article  CAS  Google Scholar 

  48. Nakane Y, Takeda T, Hoshino N, Sakai KI, Akutagawa T (2015) J Phys Chem A 119:6223–6231.

  49. Bissell RA, de Silva AP, Gunaratne HQN, Lynch PLM, Maguire GEM, Sandanayake KRAS (1992) Chem Soc Rev 21:187–195.

  50. Kumari S, Joshi S, SMA S, Agarwal D, Panda SS, Pant DD, Sakhuja R (2015) Aus. J Chem 68:1415–1426

    CAS  Google Scholar 

  51. Kumari S, Joshi S, Cordova-Sintjago TC, Pant DD, Sakhuja R (2016) Sens. Actuators B: Chem 229:599–608

    Article  CAS  Google Scholar 

  52. Mishra H, Pant D, Pant TC, Tripathi HB (2006) J Photochem Photobiol A Chem 177:197–204

    Article  CAS  Google Scholar 

  53. Ranjitha C, Vijayana KK, Praveena VK, Saleesh NS (2010) Spectrochim. Acta Part A 75:1610–1616

    Article  Google Scholar 

  54. Frisch MJ (2009) Gaussian 09, Revision D.01, Gaussian, Inc., Wallingford CT

  55. Becke AD (1993) J Chem Phys 98:5648–5652.

  56. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785–789.

  57. Stratmann RE, Scuseria GE, Frisch MJ (1998) J Chem Phys 109:8218–8224

  58. Casida M E, Jamorski C, Casida KC, Salahub DR (1998) J Chem Phys 108: 4439–4445.

  59. Miertuš S, Scrocco E, Tomasi J (1981) Chem Phys 55:117–129.

  60. Miertuš S, Tomasi J (1982) Chem Phys 65:239–241.

  61. Lin W, Long L, Feng J, Wang B, Guo C (2007) Eur J Org Chem 26: 4301–4304

  62. Onderwater RCA, Venhorst J, Commandeur JNM, Vermeulen NPE (1999) Chem Res Toxicol 12:555–559.

  63. Zhang F, Wang L, Chang SH, Huang KL, Chi Y, Hung WY, Chen CM, Lee GH, Chou PT (2013) Dalton Trans 42:7111–7119.

  64. Neupane LN, Kim JM, Lohani CR, Lee KH (2012) J Mater Chem 22: 4003–4008.

  65. Yang MH, Thirupathi P, Lee KH (2011) Org Lett 13:5028–5031.

  66. Benesi HA, Hilderbrand JH (1949) J Am Chem Soc 71:2703–2707.

  67. Sun YL, Wu AT (2013) J Fluoresc 23: 629–634.

  68. Bryan AJ, de Silva AP, de Silva SA, Rupasinghe RADD, Sandanayake KRAS (1989) Biosensors 4:169–179

    Article  CAS  Google Scholar 

  69. Bissell RA, de Silva AP, Gunaratne HQN, Lynch PLM, Maguire GE M, Sandanayake KRAS (1992) Chem Soc Rev 21:187–195.

  70. He H, Mortellaro MA, Leiner MJP, Young ST, Fraatz RJ, Tusa JK (2003) Anal Chem 75:549–555.

  71. Suresh M, Mandal AK, Saha S, Suresh E, Mandoli A, Liddo RD, Parnigotto PP, Das A (2010) Org Lett 12: 5406–5409.

  72. Yin S, Zhang J, Feng HK, Zhao Z, Xu L, Qiu H, Tang B (2012) Dyes Pigments 95:174–179.

  73. Jayabharathi J, Thanikachalam V, Jayamoorthy K (2012) Spectrochim Acta A 95:143–147.

Download references

Acknowledgments

The authors acknowledge the Department of Science & Technology (DST), New Delhi, for research funding (SB/FT/CS-033/2012). SK is thankful to University Grants Commission (UGC), New Delhi for Senior Research Fellowship.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Rajeev Sakhuja.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kumari, S., Joshi, S., Sarmah, A. et al. Highly Selective Sensing of Li+ in H2O/CH3CN via Fluorescence ‘Turn-on’ Response of a Coumarin-Indole Linked Dyad: an Experimental and Theoretical Study. J Fluoresc 26, 2177–2185 (2016). https://doi.org/10.1007/s10895-016-1913-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-016-1913-1

Keywords

Navigation