Schiff bases of 1,5-diarylpent-4-ene-1,3-diones and their metal complexes: Synthesis, characterization and fluorescent studies

Authors

  • Muhammed Basheer Ummathur Department of Chemistry, KAHM Unity Women’s College, Manjeri, Kerala-676122, India https://orcid.org/0000-0002-9894-7176
  • Radhika Pallikkavil Department of Chemistry, University of Calicut, Kerala-673635, India
  • Krishnannair Krishnankutty Department of Chemistry, University of Calicut, Kerala-673635, India

DOI:

https://doi.org/10.2298/JSC200520062U

Keywords:

o-aminophenol, imine-enamine form, tetradentate coordination, spectral data.

Abstract

Four Schiff bases (H2L1 to H2L4) have been synthesized by the con­densation between o-aminophenol and unsaturated diketones (1,5-diarylpent-4--ene-1,3-diones). Analytical, IR, 1H NMR and mass spectral data revealed their existence in the imine-enamine form. Dibasic tetradentate coordination of the Schiff bases in their ML complexes [M = Cu(II), Ni(II), Co(II), Zn(II), Cd(II), and Hg(II)] has been established on the basis of physical, analytical and spectral data. The fluorescent studies of H2L4 show that fluorescence emission maxima shift with increase in polarity and hydrogen bonding ability of the solvent. Paramagnetic Cu(II), Ni(II) and Co(II) ions decrease the fluorescence intensity with increase in concentration of the metal ion while diamagnetic Zn(II), Cd(II) and Hg(II) ions have very little influence on the intensity of fluorescence of the Schiff base H2L4 .

References

N. E. Borisova, V. V. Roznyatovskii, M. D. Reshetova, Y. A. Ustynyuk, Russian J. Org. Chem. 41 (2005) 1005 (https://doi.org/10.1007/s11178-005-0285-9)

R. Pallikkavil, M. B. Ummathur, K. Krishnankutty, Arch. Appl. Sci. Res. 4 (2012) 2223

G. G. Mohamed, M. M. Omar, A. M. Hindy, Turk. J. Chem. 30 (2006) 361

K. Krishnankutty, P. Sayudevi, M. B. Ummathur, J. Serb. Chem. Soc. 72 (2007) 1075 (https://doi.org/10.2298/JSC0711075K)

P. D. Benny, J. L. Green, H. P. Engelbrecht, C. L. Barnes, S. S. Jurisson, Inorg. Chem. 44 (2005) 2381 (https://doi.org/10.1021/ic048670j)

T. D. Thangadurai, K. Natarajan, Synth. React. Inorg. Met.-Org. Chem. 31 (2000) 549 (https://doi.org/10.1081/SIM-100104786)

N. Raman, Y. Pitchaikaniraja, A. Kulandaisami, Proc. Ind. Acad. Sci. (Chem. Sci). 113 (2001) 183

K. Krishnankutty, M. B. Ummathur, P. Sayudevi, J. Argent. Chem. Soc. 96 (2008) 13

T. J. Saritha, P. Metilda, Int. J. Eng. Trends Appl. 5 (2018) 1

M. Ahmed, M. A. Qadir, M. I. Shafiq, M. Muddassar, Z. Q. Samra, A. Hameed, Arab. J. Chem. 12 (2019) 41 (https://dx.doi.org/10.1016/j.arabjc.2016.11.017)

K. Krishnankutty, V. D. John, Synth. React. Inorg. Met.-Org. Chem. 33 (2003) 343 (https://doi.org/10.1081/SIM-120017791)

J. L. Funk, J. B. Frye, J. N. Oyarzo, H. Zhang, B. N. Timmermann, J. Agric. Food Chem. 58 (2010) 842 (https://doi.org/10.1021/jf9027206)

V. D. John, M. B. Ummathur, K. Krishnankutty, J. Coord. Chem. 66 (2013) 1508 (https://doi.org/10.1080/00958972.2013.784281)

R. Pallikkavil, M. B. Ummathur, K. Krishnankutty, Res. J. Chem. Sci. 5 (2015) 40

C. F. Chignell, P. Bilski, K. J. Reszka, A. G. Motten, R. H. Sik, T. A. Dahl, Photochem. Photobiol. Sci. 59 (1994) 295 (https://doi.org/10.1111/j.1751-1097.1994.tb05037.x)

M. Griesser, V. Pistis, T. Suzuki, N. Tejera, D. A. Pratt, C. Schneider, J. Biol. Chem. 286 (2011) 1114 (https://doi.org/10.1074/jbc.M110.178806)

K.T. Kazantzis, K. Koutsonikoli, B. Mavroidi, M. Zachariadis, P. Alexiou, M. Pelecanou, K. Politopoulos, E. Alexandratou, M. Sagnou, Photochem. Photobiol. Sci. 19 (2020) 193 (https://doi.org/10.1039/C9PP00375D)

E. F. Oliveira, J. V. Tosati, R. Tikekar, A. R. Monteiro, N. Nitin, Postharvest Biol. Tec. 137 (2018) 86 (http://doi.org/10.1016/j.postharvbio.2017.11.014).

L. Nardo, A. Andreoni, M. Masson, T. Haukvik, H. H. Tonnesen, J. Fluoresc. 21 (2011) 627 (https://doi.org/10.1007/s10895-010-0750-x)

R. Ghosh, D. K. Palit, Photochem. Photobiol. Sci. 12 (2013) 987 (https://doi.org/10.1039/C3PP25429A)

M. Paul, P. Venugopalan, K. Krishnankutty, Asian J. Chem. 14 (2002) 1335

M. B. Ummathur, A. Krishnan, M. P. Ukken, J. Iran. Chem. Res. 3 (2010) 71 (http://jicr.iau-arak.ac.ir/article_517487_00fd978bde4e478354207cffc21a5c24.pdf)

M. P. Ukken, M. B. Ummathur, Arch. Appl. Sci. Res. 5 (2013) 247 (https://www.scholarsresearchlibrary.com/articles/synthesis-and-characterization-of-two-conjugated-bdiketones-and-their-metal-complexes.pdf)

L. J. Bellamy, The Infrared Spectra of Complex Molecules, Chapman and Hall, London, 1980

K. Nakamoto, Infrared Spectra of Inorganic and Coordination Compounds, Wiley, New York, 1970

A. Lycka, J. Jirman, A. Cee, Mag. Res. Chem. 28 (1990) 408 (https://doi.org/10.1002/mrc.1260280505)

H. Budzikiewicz, C. Djerassi, D. H. Williams, Mass Spectrometry of Organic Compounds, Holden Day, San Francisco, CA, 1967

K. Ray, T. Weyhermüller, F. Neese, K. Wieghardt, Inorg. Chem. 44 (2005) 5345 (https://doi.org/10.1021/ic0507565)

Y. Sasaki, Bull. Inst. Chem. Res., Kyoto Univ. 8 (1980) 187 (http://hdl.handle.net/2433/76881)

K. S. Melha, J. Coord. Chem. 61 (2008) 2053 (https://doi.org/10.1080/00958970701862167)

M. M. Enriquez, M. Fuciman, A. M. LaFountain, N. L. Wagner, R. R. Birge, H. A. Frank, J. Phys. Chem., B 114 (2010) 12416 (https://doi.org/10.1021/jp106113h)

P. H. Bong, Bull. Korean Chem. Soc. 21 (2000) 81

J. H. Chang, Y. M. Choi, Y. K. Shin, Bull. Korean Chem. Soc. 22 (2001) 527

M. C. DeRosa, R. J. Crutchley, Coord. Chem. Rev. 233 (2002) 351 (https://doi.org/10.1016/S0010-8545(02)00034-6)

R. Pallikkavil, M. B. Ummathur, K. Krishnankutty, Turk. J. Chem. 37 (2013) 889 (https://doi.org/10.3906/kim-1301-19).

Published

2021-01-30

How to Cite

[1]
M. B. Ummathur, R. Pallikkavil, and K. Krishnankutty, “Schiff bases of 1,5-diarylpent-4-ene-1,3-diones and their metal complexes: Synthesis, characterization and fluorescent studies”, J. Serb. Chem. Soc., vol. 86, no. 1, pp. 39-49, Jan. 2021.

Issue

Section

Inorganic Chemistry