Skip to main content
Log in

Synthesis, characterization and biological evaluation of coordination polymers synthesized from 2,5-bis(p-tolylcarbamoyl)terephthalic acid

  • Research Article
  • Published:
International Journal of Plastics Technology

Abstract

A novel ligand 2,5-bis(p-tolylcarbamoyl)terephthalic acid (3) was synthesized by using pyromellitic dianhydride (1) with p-toluidine (2). Novel coordination polymers 4(a-f) of this ligand were prepared by using various metal salts viz. Mn(II), Fe(II), Co(II), Ni(II), Cu(II) and Zn(II). The coordination polymers and ligand were characterized by physicochemical, thermogravimetric and spectroscopic techniques. Electronic spectral analysis and magnetic measurement studies were taken into account for the geometry of coordination polymers. Polymeric properties like, Number average molecular weight (\( \overline{\mathrm{Mn}} \)) and Degree of polymerization (DP) has also been carried out. Antimicrobial activity was carried out against various strains of bacteria and spores of fungi. Compounds (3 and 4a–f) were evaluated for their antibacterial activity against Gram-positive bacterial strains (Bacillus subtilis [BS] and Staphylococcus aureus [SA]) and Gram-negative bacterial strains (Salmonella typhimurium [ST] and Escherichia coli [EC]) utilizing the agar diffusion assay. Growth inhibition was compared with the standard drug ciprofloxacin. Compounds (3 and 4a–f) were also examined for antifungal activity against different fungal strains, i.e. Penicillium expansum [PE], Botryodiplodia theobromae [BT], Nigrospora sp. [NS], Trichothesium sp. [TS]. The antifungal drug, ketoconazole was used as a positive control.

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

Similar content being viewed by others

References

  1. Allendorf MD, Bauer CA, Bhaktaa RK, Houka RJT (2009) Luminescent metal–organic frameworks. Chem Soc Rev 38:1330–1352

    Article  CAS  Google Scholar 

  2. Ma S, Sun D, Forster PM, Yuan D, Zhuang W, Chen YS, Parisez JB, Zhou HC (2009) A three-dimensional porous metal − organic framework constructed from two-dimensional sheets via interdigitation exhibiting dynamic features. Inorg Chem 48:4616–4618

    Article  CAS  Google Scholar 

  3. Sun D, Xu QJ, Ma CY, Zhang N, Huang RB, Zheng LS (2010) Self-assembly, thermal stability and photoluminescence of two mixed-ligand silver(I) networks via 2D-2D and 2D-3D parallel interpenetration of (4,4) nets. Cryst Eng Comm 12:4161–4167

    Article  CAS  Google Scholar 

  4. Pan ZR, Xu J, Yao XQ, Li YZ, Guo ZJ, Zheng HG (2011) Syntheses, structures, magnetic and photoluminescence properties of metal–organic frameworks based on aromatic polycarboxylate acids. Cryst Eng Comm 13:1617–1624

    Article  CAS  Google Scholar 

  5. Sun D, Liu FJ, Huang RB, Zheng LS (2013) Structural diversity of Ag/3-nitrophthalate coordination polymers controlled by solvent and induction agent. Cryst Eng Comm 15:1185–1193

    Article  CAS  Google Scholar 

  6. Sun D, Wei ZH, Yang CF, Wang DF, Zhang N, Huang RB, Zheng LS (2011) pH-Dependent Ag(I) coordination architectures constructed from 4-cyanopyridine and phthalic acid: from discrete structure to 2D sheet. Cryst Eng Comm 13:1591–1601

    Article  CAS  Google Scholar 

  7. Zhao F, Jing S, Che Y, Zheng J (2012) Metal–ligand ratio-controlled assembly of two pairs of Co(II) complexes: syntheses, structures and magnetic properties. Cryst Eng Comm 14:4478–4485

    Article  CAS  Google Scholar 

  8. Li HH, Ma N, Li KH (2012) A 3d mesomeric supramolecular structure of a cu(ii) coordination polymer with 1,1′-biphenyl-2,2′,3,3′ tetracarboxylic acid and 5,5′-dimethyl-2,2′-bipyridine ligands. J Inorg Organomet Polym 22(6):1320–1324

    Article  CAS  Google Scholar 

  9. Tong ML, Hu S, Wang J, Kitagawa S, Ng SW (2005) Supramolecular isomerism in cadmium hydroxide phases. Temperature-dependent synthesis and structure of photoluminescent coordination polymers of ∞- and β-Cd2(OH)2(2,4-pyda). Cryst Growth Des 5:837–839

    Article  CAS  Google Scholar 

  10. Wu ST, Long LS, Huang RB, Zheng LS (2007) pH-dependent assembly of supramolecular architectures from 0D to 2D networks. Cryst Growth Des 7:1746–1752

    Article  CAS  Google Scholar 

  11. Lu WG, Jiang L, Lu TB (2010) Lanthanide contraction and temperature-dependent structures of lanthanide coordination polymers with imidazole-4,5-dicarboxylate and oxalate. Cryst Growth Des 10:4310–4318

    Article  CAS  Google Scholar 

  12. Hagrman PJ, Hagrman D, Zubieta J (1999) Organic–inorganic hybrid materials: from “simple” coordination polymers to organodiamine-templated molybdenum oxides. Angew Chem Int Ed 38(18):2638–2684

    Article  Google Scholar 

  13. Khlobystov AN, Blake AJ, Champness NR, Lemenovskii DA, Majouga AG, Zyk NV, Schröder M (2001) Supramolecular design of one-dimensional coordination polymers based on silver(I) complexes of aromatic nitrogen-donor ligands. Coord Chem Rev 222:155–192

    Article  CAS  Google Scholar 

  14. Yaghi OM, Keeffe MO, Ockwig NW, Chae HK, Eddaoudi M, Kim J (2003) Reticular synthesis and the design of new materials. Nature 423:705–714

    Article  CAS  Google Scholar 

  15. Moulton B, Zaworotko M (2001) From molecules to crystal engineering: supramolecular isomerism and polymorphism in network solids. Chem Rev 101:1629–1639

    Article  CAS  Google Scholar 

  16. Du M, Jiang XJ, Zhao XJ (2006) Controllable assembly of metal-directed coordination polymers under diverse conditions: a case study of the mii − H3tma/Bpt mixed-ligand system. Inorg Chem 45:3998–4006

    Article  CAS  Google Scholar 

  17. Paz FAA, Klinowski J (2004) Two- and three-dimensional cadmium − organic frameworks with trimesic acid and 4,4′-trimethylenedipyridine. Inorg Chem 43:3882–3893

    Article  CAS  Google Scholar 

  18. Abourahma H, Moulton B, Kravtsov V, Zaworotko MJ (2002) Supramolecular isomerism in coordination compounds: nanoscale molecular hexagons and chains. J Am Chem Soc 124:9990–9991

    Article  CAS  Google Scholar 

  19. Varughese S, Pedireddi VR (2006) A competitive molecular recognition study: syntheses and analysis of supramolecular assemblies of 3,5-dihydroxybenzoic acid and its bromo derivative with some n-donor compounds. Chem Eur J 12(6):1597–1600

    Article  CAS  Google Scholar 

  20. Wang XL, Qin C, Wang EB (2006) Polythreading of infinite 1d chains into different structural motifs: Two poly(pseudo-rotaxane) architectures constructed by concomitant coordinative and hydrogen bonds. Cryst Growth Des 6:439–443

    Article  CAS  Google Scholar 

  21. Yang GP, Wang YY, Ma LF, Liu JQ, Wu YP, Wu WP, Shi QZ (2007) Hydrothermal syntheses and characterizations of three coordination polymers based on mixed organic ligands. Eur J Inorg Chem 24:3892–3898

    Article  Google Scholar 

  22. Wang JJ, Gou L, Hu HM, Han ZX, Li DS, Xue GL, Yang ML, Shi QZ (2007) Ligand and pH-controlled Zn(II) bilayer coordination polymers based on biphenyl-3,3′,4,4′-tetracarboxylate. Cryst Growth Des 7:1514–1521

    Article  CAS  Google Scholar 

  23. Zang SQ, Su Y, Li YZ, Ni ZP, Zhu HZ, Meng QJ (2006) Interweaving of triple-helical and extended metal − o − metal single-helical chains with the same helix axis in a 3d metal − organic framework. Inorg Chem 45(10):3855–3857

    Article  CAS  Google Scholar 

  24. Duan X, Lin J, Li Y, Zhu C, Meng Q (2008) Syntheses, structures and properties of a series of organic–inorganic complexes based on methylenediisophthalic acid (H4MDIP). Cryst Eng Comm 10:207–216

    Article  CAS  Google Scholar 

  25. Zang S, Su Y, Duan C, Li Y, Zhu H, Meng Q (2006) Coexistence of chiral hydrophilic and achiral hydrophobic channels in one multi-helical-array metal–organic framework incorporating helical water cluster chains. Chem Commun 4997–4999

  26. Zang SQ, Su Y, Li YZ, Lin JG, Duan XY, Meng QJ, Gao S (2009) Four 2D metal–organic networks incorporating Cd-cluster SUBs: hydrothermal synthesis, structures and photoluminescent properties. Cryst Eng Comm 11:122–129

    Article  CAS  Google Scholar 

  27. Mei CZ, Shan WW, Liu BT (2011) Synthesis, crystal structure and luminescent properties of one 3D Cd(II) coordination polymer [Cd(H3BPTC)2(bpy)]n (H4BPTC = 1,1′-biphenyl-2,2′,6,6′-tetracarboxylic acid, bpy = 4,4′-bipyridine). Spectrochim Acta A Mol Biomol Spectrosc 81(1):764–768

    Article  CAS  Google Scholar 

  28. Mei CZ, Wang JX, Shan WW (2011) Synthesis and crystal structure of an infinitesandwich-type Cu(i) coordination polymer:{[Cu(abpy)2](H3bptc)·(H2O)}n constructedby a tetracarboxylic acid. Chin J Struct Chem 8:1194–1198

    Google Scholar 

  29. Huang YG, Gong YQ, Jiang FL, Yuan DQ, Wu MY, Gao Q, Wei W, Hong MC (2007) Formation of an infinite three-dimensional water network by the hierarchic assembly of bilayer water nanotubes of octamers. Cryst Growth Des 7:1385–1387

    Article  CAS  Google Scholar 

  30. Patel YS, Patel HS, Srinivasulu B (2012) Synthesis, spectral, magnetic, thermal and biological aspects of pyromellitic dianhydride based co-ordination polymers. Int J Plast Technol 16(2):117–124

    Article  CAS  Google Scholar 

  31. Patel YS, Patel HS (2012) Co-ordination polymers derived from pyromellitic diamic acid: synthetic, spectral, magnetic, thermal and biological aspects. Elixir Appl Chem 44:7238–7242

    Google Scholar 

  32. Patel YS, Patel KD, Patel HS (2012) Spectral and antimicrobial studies on novel ligand and its co-ordination polymers Journal of Saudi Chemical Society. http://dx.doi.org/10.1016/j.jscs.2012.11.008

  33. Vanparia SF, Patel TS, Sojitra NA, Jagani CL, Dixit BC, Patel PS, Dixit RB (2010) Synthesis, characterization and antimicrobial study of novel 4-{[(8-hydroxyquinolin-5-yl)methyl]amino} benzenesulfonamide and its oxinates. Acta Chim Slov 57:660–667

    CAS  Google Scholar 

  34. Vogel AI (1961) A textbook of quantitative inorganic analysis, 3rd edn. Longman, London

    Google Scholar 

  35. Jeffery GH, Bassett J, Mentham J, Denney RC (1989) Vogel’s textbook of quantitative inorganic analysis, 5th edn. Longman, Harlow

    Google Scholar 

  36. Chatterjee SK, Gupta ND (1973) Effects of structure and composition on the titration curves of some synthetic copolymers in nonaqueous media. J Polym Sci Polym Chem Ed 11:1261–1270

    Article  CAS  Google Scholar 

  37. Alam S (2004) Synthesis, antibacterial and antifungal activity of some derivatives of 2-phenyl-chromen- 4-one. J Chem Sci 116:325–332

    Article  CAS  Google Scholar 

  38. Pelzar MJ, Chan ECS, Krieg NR (1998) Antibiotics and other chemotherapeutic agents in microbiology, 5th edn. Blackwell Science, New York

    Google Scholar 

  39. Silverstein RM, Webste FX (2004) Spectrometric identification of organic compounds, 6th edn. John Wiley & Sons, New York

    Google Scholar 

  40. Panchal PK, Pansuriya PB, Patel MN (2006) In-vitro biological evaluation of some ONS and NS donor Schiff’s bases and their metal complexes. J Enz Inhib Med Chem 21:453–458

    Article  CAS  Google Scholar 

  41. Nakamoto K (1978) Infrared and raman spectra of inorganic and coordination compounds, 3rd edn. Wiley, New York

    Google Scholar 

  42. Lever ABP (1984) Electronic spectra of dn inorganic electronic spectroscopy, 2nd edn. Elsevier, Amsterdam

    Google Scholar 

  43. Malik A, Parveen S, Ahamad T, Alshehri SM, Singh PK, Nishat N (2010) Coordination polymer: synthesis spectral characterization and thermal behaviour of starch-urea based biodegradable polymer and its PolymerMetal complexes. Bioinorg Chem Appl. doi:10.1155/2010/848130

    Google Scholar 

  44. Soliman EM, El-Shabasy M (1994) Synthesis, characterization and electrical conductivity properties of homo- and hetero-di and trimetallic complexes of mixed azo dyes. J Mater Sci 29:4505–4509

    Article  CAS  Google Scholar 

  45. Lewis J, Wilkins RS (1960) Modern co-ordination chemistry. Wiley Interscience, New York

    Google Scholar 

  46. Papplardo R (1960) Note on the optical absorption of MnCl2 and MnBr2. J Chem Phys 33:613–614

    Article  Google Scholar 

  47. Tweedy BG (1964) Plant extracts with metal ions as potential antimicrobial agents. Phytopathology 55:910–914

    Google Scholar 

  48. Chohan ZH, Arif M, Shafiq Z, Yaqub M, Supuran CT (2006) In vitro antibacterial, antifungal & cytotoxic activity of some isonicotinoylhydrazide Schiff’s bases and their cobalt (II), copper (II), nickel (II) and zinc (II) complexes. J Enzym Inhib Med 21(1):95–103

    Article  CAS  Google Scholar 

  49. Chohan ZH, Supuran CT (2005) Organometallic compounds with biologically active molecules: in vitro antibacterial and antifungal activity of some 1,1′-(dicarbohydrazono) ferrocenes and their cobalt(II), copper(II), nickel(II) and zinc(II) complexes. Appl Organomet Chem 19(12):1207–1214

    Article  CAS  Google Scholar 

Download references

Acknowledgments

One of the authors Yogesh S. Patel is greatly thankful to UGC for sanctioning his Teacher Fellowship Under the Scheme of Faculty Improvement Programme for the research work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yogesh S. Patel.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Patel, Y.S., Patel, H.S. & Srinivasulu, B. Synthesis, characterization and biological evaluation of coordination polymers synthesized from 2,5-bis(p-tolylcarbamoyl)terephthalic acid. Int J Plast Technol 18, 49–63 (2014). https://doi.org/10.1007/s12588-014-9064-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12588-014-9064-1

Keywords

Navigation