Skip to main content
Log in

“Estimation of Ground and Excited State Dipole Moments of aryl Boronic acid Derivative by Solvatochromic Shift Method”

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

Abstract

In the present work, the absorption and fluorescence spectra of newly synthesized aryl boronic acid derivative namely 2-Methylphenyl boronic acid (2MPBA) have been recorded in various solvents of different polarities. The ground state dipole moment of 2MPBA was obtained from quantum chemical calculations. Solvatochromic correlations were used to estimate the ground state (μ g ) and excited state (μ e ) dipole moments. The excited state dipole moments are observed to be greater than the ground state dipole moment and ground and excited state dipole moments are not parallel but subtend by an angle of 880. Further, the changes in dipole moment (Δμ) were calculated both from solvatochromic shift method and microscopic solvent polarity parameter (E N T ), and the value are compared. The spectral variations were analyzed by Kamlet-Taft parameters.

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.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Chaofeng D, Yunfeng C, Jianmei C, Binghe W (2010) Molecules 15:5768–5781

    Article  Google Scholar 

  2. Dennis G. Hall, Boronic acids: preparation and applications in organic synthesis 2nd completely revised edition (2011)

  3. Lackowicz JR (1983) Principle of fluorescence spectroscopy. Plenum Press, New York

    Book  Google Scholar 

  4. K. K. Rohtagi–Mukherjee Fundamentals of Photochemistry, Wiley Eastern Ltd., (1992)

  5. Koutek B (1978) Collect Czech Chem Commun 43:2368–2386

    Article  CAS  Google Scholar 

  6. Kawski A, Kuklinski B, Bojarski P (2007) Chem Phys Lett 448:208–212

    Article  CAS  Google Scholar 

  7. Raikar US, Renuka CG, Nadaf YF, Mulimani BG, Karguppikar AM, Soudagar MK (2006) Spectrochim Acta A 65:673–677

    Article  CAS  Google Scholar 

  8. Biradar DS, Siddlingeshwar B, Hanagodimath SM (2008) J Mol Struct 875:108–112

    Article  CAS  Google Scholar 

  9. Lippert E (1957) Z Elektrochem 61:962–975

    CAS  Google Scholar 

  10. Bakshiev NG (1964) Opt Spectrosk 16:821–832

    Google Scholar 

  11. L. Bilot, A. Kawski, Z. Naturforsch. 18A (1963) 10–256

  12. L. Bilot, A. Kawski, Z. Naturforsch. 17A (1962) 621–627

  13. Chamma A, Viallet P, Acad CR (1970) Sci Paris Ser C 270:1901–1904

    CAS  Google Scholar 

  14. Katritzky AR, Fara DC, Yang H, Tamm K, Tamm T, Karelson M (2004) Chem Rev 104(1):175–198

    Article  CAS  PubMed  Google Scholar 

  15. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 2nd ed., VCH, 1988.

  16. Raveendra M, Melavanki NR, Patil SB, Kapatkar NH, Ayachit SU, Thipperudrappa J, Nataraju AR (2011) J Mol Liq 2:105–110

    Google Scholar 

  17. Raveendra M, Melavanki HD, Patil SU, Kadadevarmath JS (2012) J Fluoresc 22:137–144

    Article  Google Scholar 

  18. Patil NR, Melavanki RM, Chougala BM, Shastri LA, Sanningannavar FM (2012) Int J Life Sc Pharm & Sci 2(2):139–149

    Google Scholar 

  19. Nagaraja D, Patil NR, Kusanur RA, Patil HD, Melavanki RM (2013) Int J Life Sc Pharm & Sci 3(1):54–64

    CAS  Google Scholar 

  20. Patil SN, Sanningannavar FM, Navati BS, Patil NR, Kusanur RA, Melavanki RM (2014) Int J Life Sc Pharm & Sci 4(1):12–20

    Google Scholar 

  21. Patil NR, Melavanki RM, Kapatkar SB, Ayachit NH, Saravanan J (2011) J Flurosec 21:1213–1222

    Article  CAS  Google Scholar 

  22. Kadadevarmath JS, Malimath GH, Patil NR, Geethanjali HS, Melavanki RM (2013) Can J Phys 91:1107–1113

    Article  CAS  Google Scholar 

  23. Thipperudrappa J (2014) Mapana J Sci 14(1):103–119

    Google Scholar 

  24. Thipperudrappa J, Biradar DS, Manohara SR, Hanagodimath SM, Inamadar SR, James RM (2008) Spectrochim Acta A Part A 69(3):991–997

    Article  CAS  Google Scholar 

  25. Raikar US, Tangod VB, Mastiholi BM, Sreenivasa S (2010) Afr J Pure and Appl Chem 4(9):188–197

    CAS  Google Scholar 

  26. Nagachandra KH, Mannekutla JR, Amarayya SM, Inamdar SR (2012) Eur J Chem 3(2):163–171

    Article  Google Scholar 

  27. Joshi S, Pant DD (2012) J Mol Liq 166:49–52

    Article  CAS  Google Scholar 

  28. Sıdır YG, Sıdır I (2013) Spectrochim Acta A 102:286–296

    Article  Google Scholar 

  29. Jayabharathi J, Thanikachalam V, Srinivasan N, Venkatesh M (2012) Spectrochim Acta A 90:125–130

    Article  CAS  Google Scholar 

  30. Zakerhamidi MS, Ahmadi-Kandjani S, Moghadam M, Ortyl E, Kucharski S (2011) J Mol Struc 996:95–100

    Article  CAS  Google Scholar 

  31. Gilani G, Hosseini SE, Moghadam M, Alizadeh E (2012) Spectrochim Acta A 89:231–237

    Article  Google Scholar 

  32. Kawaski A (1992) In: Rabeck JF (ed) Photochem and Photophys, 5th edn. CRC Press, Boca Raton, Ann Arbor Boston, pp 1–47

    Google Scholar 

  33. Kawaski A (1966) Acta Phys Polon 29:507–518

    Google Scholar 

  34. Reichardt C (1994) Chem Rev 94:2319–2358

    Article  CAS  Google Scholar 

  35. Ravi M, Soujnya T, Samanta A, Radhakrishnan TP, Chem J (1995) Soc Faraday Trans 91:2739–2742

    Article  Google Scholar 

  36. Kamlet MJ, Abboud JLM, Abraham MH, Taft RW (1983) J Org Chem 48:2877–2887

    Article  CAS  Google Scholar 

  37. Molander GA, Trice SLJ, Dreher SD (2010) J Am Chem Soc 132(50):17701–17703

    Article  CAS  PubMed Central  PubMed  Google Scholar 

Download references

Acknowledgments

Authors (GVM) and (NRP) thank the H.O.D., the Principal B V B College of Engineering & Technology, Hubli, India for financial support under Capacity Building Fund and K.L.E Society Management Belgaum for their encouragement. And another author (RMM) is also grateful to the H.O.D., Dr. Suguna, the Principal and the Management of M.S.R.I.T. for their continuous encouragement.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to N. R. Patil or R. M. Melavanki.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Muddapur, G.V., Patil, N.R., Patil, S.S. et al. “Estimation of Ground and Excited State Dipole Moments of aryl Boronic acid Derivative by Solvatochromic Shift Method”. J Fluoresc 24, 1651–1659 (2014). https://doi.org/10.1007/s10895-014-1452-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-014-1452-6

Keywords

Navigation