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Vol. 32 No. 8 (2020): Vol 32 Issue 8, 2020

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A Review on 2,6-Diformyl-4-methylphenol Derived Schiff Bases as Fluorescent Sensors

https://doi.org/10.14233/ajchem.2020.22644
Mrinal Sarkar
Department of Chemistry, Derozio Memorial College, Kolkata-700136, India

Corresponding Author(s) : Mrinal Sarkar

msarkar81@gmail.com

Asian Journal of Chemistry, Vol. 32 No. 8 (2020): Vol 32 Issue 8, 2020

Abstract

2,6-Diformyl-4-methylphenol fluorophore derived Schiff base sensors detect metal ions such as Zn2+, Al3+, Hg2+, Cd2+, Sn2+ and Cu2+ with high sensitivity and selectivity through changes in fluorescence intensity based on CHEF, ICT, FRET, ESIPT, C=N isomerization and PET mechanism. Several anions viz. HPO42–, H2PO4–, PO43–, AsO33–, H2AsO4–, AsO2–, PPi  (pyrophosphate), I–, F– and N3– were also detected through intermolecular hydrogen bonding (between sensor and anion) based on TICT, PET, CHEF, ESIPT and aggregation induced emission mechanism. Selectivity and sensitivity for these metal ions and anions were achieved by introducing various amines to core fluorophore 2,6-diformyl-4-methylphenol. Majority of  these fluorescent sensors were Zn2+ ion selective. Due to the filled d10 electronic configuration of Zn2+ ion usually does not show deactivation of excited state via any electron or energy transfer  mechanisms. Both solvent dependent and independent ten multi-ion selective sensors are found. This review will consolidate on 2,6-diformyl-4-methylphenol derived Schiff base fluorescent chemosensors. 

Keywords

Cell imaging Fluorescent chemosensor 2,6-Diformyl-4-methylphenol Selective multi-ion sensor
Sarkar, M. . (2020). A Review on 2,6-Diformyl-4-methylphenol Derived Schiff Bases as Fluorescent Sensors. Asian Journal of Chemistry, 32(8), 1837–1848. https://doi.org/10.14233/ajchem.2020.22644
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References
  1. A.W. Czarnik, Acc. Chem. Res., 27, 302 (1994); https://doi.org/10.1021/ar00046a003
  2. A.T. Wright and E.V. Anslyn, Chem. Soc. Rev., 35, 14 (2006); https://doi.org/10.1039/B505518K
  3. V. Amendola and L. Fabbrizzi, Chem. Commun., 513 (2009); https://doi.org/10.1039/b808264m
  4. L. Prodi, New J. Chem., 29, 20 (2005); https://doi.org/10.1039/b411758a
  5. J. Yoon, S.K. Kim, N.J. Singh and K.S. Kim, Chem. Soc. Rev., 35, 355 (2006); https://doi.org/10.1039/b513733k
  6. A.W. Czarnik, Instrumen. Sci. Technol., 22, 405 (1994);https://doi.org/10.1080/10739149408001201
  7. A.P.S. Gonzáles, M.A. Firmino, C.S. Nomura, F.R.P. Rocha, P.V. Oliveira and I. Gaubeur, Anal. Chim. Acta, 636, 198 (2009); https://doi.org/10.1016/j.aca.2009.01.047
  8. J.S. Becker, A. Matusch, C. Depboylu, J. Dobrowolska and M.V. Zoriy, Anal. Chem., 79, 6074 (2007); https://doi.org/10.1021/ac0700528
  9. Y. Liu, P. Liang and L. Guo, Talanta, 68, 25 (2005); https://doi.org/10.1016/j.talanta.2005.04.035
  10. A.A. Ensafi, T. Khayamian, A. Benvidi and E. Mirmomtaz, Anal. Chim. Acta, 561, 225 (2006); https://doi.org/10.1016/j.aca.2006.01.015
  11. Y.H. Hung, A.I. Bush and R.A. Cherny, J. Biol. Inorg. Chem., 15, 61 (2010); https://doi.org/10.1007/s00775-009-0600-y
  12. B.-C. Yin, B.-C. Ye, W. Tan, H. Wang and C.-C. Xie, J. Am. Chem. Soc., 131, 14624 (2009); https://doi.org/10.1021/ja9062426
  13. T.-W. Lin and S.-D. Huang, Anal. Chem., 73, 4319 (2001); https://doi.org/10.1021/ac010319h
  14. G. Sivaraman, T. Anand and D. Chellappa, RSC Adv., 3, 17029 (2013); https://doi.org/10.1039/c3ra42109k
  15. M. Suresh, A. Ghosh and A. Das, Chem. Commun., 3906 (2008); https://doi.org/10.1039/b807290f
  16. V. Bhalla, V. Vij, M. Kumar, P.R. Sharma and T. Kaur, Org. Lett., 14, 1012 (2012); https://doi.org/10.1021/ol203339c
  17. A. Kumar, A. Kumar and D.S. Pandey, Dalton Trans., 45, 8475 (2016); https://doi.org/10.1039/C6DT00747C
  18. P.S. Hariharan and S.P. Anthony, Anal. Chim. Acta, 848, 74 (2014); https://doi.org/10.1016/j.aca.2014.07.042
  19. K.-L. Han and G.-J. Zhao, Hydrogen Bonding and Transfer in the Excited State, Wiley (2010).
  20. A. Gupta and N. Kumar, RSC Adv., 6, 106413 (2016); https://doi.org/10.1039/C6RA23682K
  21. M. Formica, V. Fusi, L. Giorgi and M. Micheloni, Coord. Chem. Rev., 256, 170 (2012); https://doi.org/10.1016/j.ccr.2011.09.010
  22. J. Wu, W. Liu, J. Ge, H. Zhang and P. Wang, Chem. Soc. Rev., 40, 3483 (2011); https://doi.org/10.1039/c0cs00224k
  23. S. Anbu, R. Ravishankaran, M.F.C. Guedes da Silva, A.A. Karande and A.J.L. Pombeiro, Inorg. Chem., 53, 6655 (2014); https://doi.org/10.1021/ic500313m
  24. M. Sarkar, S. Banthia and A. Samanta, Tetrahedron Lett., 47, 7575 (2006); https://doi.org/10.1016/j.tetlet.2006.08.091
  25. P. Roy, K. Dhara, M. Manassero, J. Ratha and P. Banerjee, Inorg. Chem., 46, 6405 (2007); https://doi.org/10.1021/ic700420w
  26. K. Sarkar, K. Dhara, M. Nandi, P. Roy, A. Bhaumik and P. Banerjee, Adv. Funct. Mater., 19, 223 (2009); https://doi.org/10.1002/adfm.200800888
  27. A. Jana, P.K. Sukul, S.K. Mandal, S. Konar, S. Ray, K. Das, J.A. Golen, A.L. Rheingold, S. Mondal, T.K. Mondal, A.R. Khuda-Bukhsh and S.K. Kar, Analyst, 139, 495 (2014); https://doi.org/10.1039/C3AN01750H
  28. C. Patra, A.K. Bhanja, C. Sen, D. Ojha, D. Chattopadhyay, A. Mahapatra and C. Sinha, RSC Adv., 6, 53378 (2016); https://doi.org/10.1039/C6RA07089B
  29. A. Jana, B. Das, S.K. Mandal, S. Mabhai, A.R. Khuda-Bukhsh and S. Dey, New J. Chem., 40, 5976 (2016); https://doi.org/10.1039/C6NJ00234J
  30. T.A. Khan, M. Sheoran, V.N. Raj M.S. Jain, D. Gupta and S.G. Naik, Spectrochim. Acta A Mol. Biomol. Spectrosc., 189, 176 (2018); https://doi.org/10.1016/j.saa.2017.08.017
  31. U.C. Saha, B. Chattopadhyay, K. Dhara, S.K. Mandal, S. Sarkar, A.R. Khuda-Bukhsh, M. Mukherjee, M. Helliwell and P. Chattopadhyay, Inorg. Chem., 50, 1213 (2011); https://doi.org/10.1021/ic1015252
  32. P. Roy, K. Dhara, M. Manassero and P. Banerjee, Inorg. Chim. Acta, 362, 2927 (2009); https://doi.org/10.1016/j.ica.2009.01.023
  33. K. Dhara, S. Karan, J. Ratha, P. Roy, G. Chandra, M. Manassero, B. Mallik and P. Banerjee, Chem. Asian J., 2, 1091 (2007); https://doi.org/10.1002/asia.200700152
  34. A.K. Bhanja, C. Patra, S. Mondal, S. Mishra, K.D. Saha and C. Sinha, Sens. Actuators B Chem., 252, 257 (2017); https://doi.org/10.1016/j.snb.2017.05.178
  35. S. Lohar, S. Pal, M. Mukherjee, A. Maji, P. Chattopadhyay and N. Demitri, RSC Adv., 7, 25528 (2017); https://doi.org/10.1039/C7RA02175E
  36. R. Purkait, A.D. Mahapatra, D. Chattopadhyay and C. Sinha, Spectrochim. Acta A Mol. Biomol. Spectrosc., 207, 164 (2019); https://doi.org/10.1016/j.saa.2018.09.019
  37. R. Purkait, S. Maity and C. Sinha, New J. Chem., 42, 6236 (2018); https://doi.org/10.1039/C7NJ04533F
  38. S. Lohar, A. Sengupta, A. Chattopadhyay, J.S. Matalobos and D. Das, Eur. J. Inorg. Chem., 2014, 5675 (2014); https://doi.org/10.1002/ejic.201402702
  39. S. Nandi and D. Das, ACS Sens., 1, 81 (2016); https://doi.org/10.1021/acssensors.5b00035
  40. B.K. Datta, D. Thiyagarajan, A. Ramesh and G. Das, Dalton Trans., 44, 13093 (2015); https://doi.org/10.1039/C5DT01468A
  41. R. Alam, T. Mistri, R. Bhowmick, A. Katarkar, K. Chaudhuri and M. Ali, RSC Adv., 5, 53940 (2015); https://doi.org/10.1039/C5RA08024J
  42. R. Purkait, S. Dey and C. Sinha, New J. Chem., 42, 16653 (2018); https://doi.org/10.1039/C8NJ03165G
  43. S. Adhikari, S. Mandal, A. Ghosh, S. Guria and D. Das, Dalton Trans., 44, 14388 (2015); https://doi.org/10.1039/C5DT02146D
  44. C. Kar, M.D. Adhikari, B.K. Datta, A. Ramesh and G. Das, Sens. Actuators B Chem., 188, 1132 (2013); https://doi.org/10.1016/j.snb.2013.08.005
  45. B. Naskar, R. Modak, D.K. Maiti, A. Bauzá, A. Frontera, P.K. Maiti, S. Mandal and S. Goswami, RSC Adv., 7, 11312 (2017); https://doi.org/10.1039/C6RA27017D
  46. V. Chandrasekhar, S. Das, R. Yadav, S. Hossain, G. Subramaniam, R. Parihar and P. Sen, Inorg. Chem., 51, 8664 (2012); https://doi.org/10.1021/ic301399a
  47. A. Banerjee, A. Sahana, S. Lohar, S. Panja, S.K. Mukhopadhyay and D. Das, RSC Adv., 4, 3887 (2014); https://doi.org/10.1039/C3RA45362F
  48. A.S.M. Islam, R. Alam, A. Katarkar, K. Chaudhuri and M. Ali, Analyst, 140, 2979 (2015); https://doi.org/10.1039/C5AN00236B
  49. S. Lohar, S. Pal, B. Sen, M. Mukherjee, S. Banerjee and P. Chattopadhyay, Anal. Chem., 86, 11357 (2014); https://doi.org/10.1021/ac503255f
  50. S. Anbu, S. Kamalraj, C. Jayabaskaran and P.S. Mukherjee, Inorg. Chem., 52, 8294 (2013); https://doi.org/10.1021/ic4011696
  51. A. Gogoi, S. Mukherjee, A. Ramesh and G. Das, Anal. Chem., 87, 6974 (2015); https://doi.org/10.1021/acs.analchem.5b01746
  52. A. Banerjee, A. Sahana, S. Lohar, B. Sarkar, S.K. Mukhopadhyay and D. Das, RSC Adv., 3, 14397 (2013); https://doi.org/10.1039/C3RA41591K
  53. U.C. Saha, S.K. Mandal, S. Pal, A.R. Khuda-Bukhsh, P. Chattopadhyay and K. Dhara, Biochem. Mol. Biol. Lett., 1, 065 (2015).
  54. M. Mukhopadhyay, D. Banerjee and S. Mukherjee, J. Phys. Chem. A, 110, 12743 (2006); https://doi.org/10.1021/jp063724r
  55. S. Mitra and S. Mukherjee, J. Lumin., 118, 1 (2006); https://doi.org/10.1016/j.jlumin.2005.04.014
  56. U.C. Saha, K. Dhara, B. Chattopadhyay, S.K. Mandal, S. Mondal, S. Sen, M. Mukherjee, S. van Smaalen and P. Chattopadhyay, Org. Lett., 13, 4510 (2011); https://doi.org/10.1021/ol201652r
  57. A. Sahana, A. Banerjee, S. Lohar, B. Sarkar, S.K. Mukhopadhyay and D. Das, Inorg. Chem., 52, 3627 (2013); https://doi.org/10.1021/ic3019953
  58. Z. Dong, X. Tian, Y. Chen, J. Hou, Y. Guo, J. Sun and J. Ma, Dyes Pigments, 97, 324 (2013); https://doi.org/10.1016/j.dyepig.2013.01.002
  59. K. Dhara, U.C. Saha, A. Dan, M. Manassero, P. Chattopadhyay and S. Sarkar, Chem. Commun., 46, 1754 (2010); https://doi.org/10.1039/b919937c
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