Skip to main content
SpringerLink
Log in

Copper(I) complexes of 2-(benzen-1-yl)methyleneamino-3-aminomaleonitrile and triphenylphosphine ligands: synthesis, characterization, luminescence and catalytic properties

  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

Abstract

Some mixed ligand copper(I) complexes of general formula [Cu(L)(PPh3)3]X (X = Cl (1), ClO4 (2), BF4 (3) or PF6 (4); L = 2-(benzen-1-yl)methyleneamino-3-aminomaleonitrile) were prepared and characterized by physicochemical and spectroscopic methods. A single-crystal X-ray diffraction study of [Cu(L)(PPh3)3]CIO4 (2) revealed that the copper atom is four coordinated in a distorted tetrahedral geometry. Electrochemical studies of complexes 1–4 show quasireversible redox behavior corresponding to the Cu(I)/Cu(II) couple. Room temperature luminescence is observed for all four complexes. These complexes proved to be effective catalysts for the Sonogashira coupling of terminal alkynes with aryl halides at 90 °C.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 3

Similar content being viewed by others

References

  1. Fitchett CM, Steel PJ (2007) Pyrazine-bridged copper(I) iodide coordination polymers: control of chain separation through ligand design. Inorg Chem Commun 10:1297–1300

    Article  CAS  Google Scholar 

  2. Ahuja R, Nethaji M, Samuelson AG (2011) Chelating and bridging bis(diphenylpho sphino)aniline complexes of copper(I). Inorg Chim Acta 372:220–226

    Article  CAS  Google Scholar 

  3. Maini L, Braga D, Mazzeo P, Ventura B (2012) Polymorph and isomer conversion of complexes based on CuI and PPh3 easily observed via luminescence. Dalton Trans 41:531–539

    Article  CAS  Google Scholar 

  4. Naik S, Mague JT, Balakrishna MS (2014) Short-Bite PNP ligand-supported rare tetranuclear [Cu4I4] clusters: structural and photoluminescence studies. Inorg Chem 53:3864–3873

    Article  CAS  Google Scholar 

  5. Chavan SS, Sawant SK, Pawal SB, More MS (2016) Copper(I) complexes of 2-methoxy-(5-trifluoromethyl-phenyl)-pyridine-2yl-methlyeneamine: impact of phosphine ancillary ligands on luminescence and catalytic properties of the copper(I) complexes. Polyhedron 105:192–199

    Article  CAS  Google Scholar 

  6. Guha A, Adhikary J, Modal TK, Das D (2011) Zinc and cadmium complexes of a Schiff base ligand derived from diaminomaleonitrile and salicylaldehyde: synthesis, characterization, photoluminescence properties and DFT study. Indian J Chem 50:1463–1468

    Google Scholar 

  7. Robertson PS, Vaughan J (1958) Derivatives of the hydrogen cyanide tetramer: structure and chemistry. J Am Chem Soc 80:2691–2693

    Article  CAS  Google Scholar 

  8. Rivera A, Ríos-Motta JRM, Leon F (2006) Revisiting the reaction between diaminomaleonitrile and aromatic aldehydes: a green chemistry approach. Molecules 11:858–866

    Article  CAS  Google Scholar 

  9. Johnson DM, Reybuck SE, Lawton RG, Ramussen PG (2005) Condensation of DAMN with conjugated aldehydes and polymerizations of the corresponding imines. Macromolecules 38:3615–3621

    Article  CAS  Google Scholar 

  10. Nesterov VV, Antipin MY, Nesterov VN, Penn BG, Frazier DO, Timofeeva TV (2004) Thermally stable imines as new potential nonlinear optical materials. Cryst Growth Des 4:521–531

    Article  CAS  Google Scholar 

  11. Hogan GA, Gallo AA, Nicholas KM, Srivastava RS (2002) Cu(I)-catalyzed allylic amination of olefins. Tetrahedron Lett 43:9505–9508

    Article  CAS  Google Scholar 

  12. Feringa BL (2000) Phosphoramidites: marvellous ligands in catalytic asymmetric conjugate addition. Acc Chem Res 33:346–353

    Article  CAS  Google Scholar 

  13. Burk MJ (2000) Modular phospholane ligands in asymmetric catalysis. Acc Chem Res 33:363–372

    Article  CAS  Google Scholar 

  14. Jacobsen EN, Pfaltz A, Yamamato H (1999) Comprehensive asymmetric catalysis. In: Hayashi T (ed) 2nd edn. Springer, New York, p 887

  15. Vogel AI (1955) Text book of practical organic chemistry, 3rd edn. Woolwich Polytechnic, London, p 190

    Google Scholar 

  16. Li D, Li R-Z, Ni Z, Qi Z-Y, Feng X-L, Cai J-W (2003) Synthesis and crystal structure of photoluminescent copper(I)–phosphine complexes with oxygen and nitrogen donor ligands. Inorg Chem Commun 6:469–473

    Article  CAS  Google Scholar 

  17. Fielden J, Long D-L, Cronin L, Kogerler P (2009) Synthesis of Cu(I) octamolybdates using tetrakis-acetonitrile copper(I) hexafluorophosphate. Polyhedron 28:2803–2807

    Article  CAS  Google Scholar 

  18. Wu S-P, Wang T-H, Liu S-R (2010) A highly selective turn-on fluorescent chemosensor for copper(II) ion. Tetrahedron 66:9655–9658

    Article  CAS  Google Scholar 

  19. Sheldrick GM (2015) Crystal structure refinement with SHELXL. Acta Cryst C 71:3–8

    Article  Google Scholar 

  20. Farrugia LJ (1997) ORTEP-3 for windows—a version of ORTEP-III with a graphical interface. J Appl Cryst 30:565

    Article  CAS  Google Scholar 

  21. Macrae CF, Edgington PR, McCarbe P, Pidcock E, Shields GP, Taylor R, Towler M, Van de Streek J (2006) Mercury visualization and analysis of crystal structure. J Appl Cryst 39:453–457

    Article  CAS  Google Scholar 

  22. Dias AR, Garcia MH, Rodrigues JC, Green MLH, Lai KK, Klueber SM (1994) Synthesis and characterization of 5-monocyclopentadienyl (p-nitrobenzonitrile) ruthenium(II) salts: second harmonic generation powder efficiencies. J Organomet Chem 475:241–245

    Article  CAS  Google Scholar 

  23. Mukharjee A, Chakrabarty R, Ng SW, Patra GK (2010) The syntheses, characterizations, X-ray crystal structures and properties of Cu(I) complexes of a bis-bidentate schiff base ligand. Inorg Chim Acta 363:1707–1712

    Article  Google Scholar 

  24. Vinogradova KA, Krivopalov VP, Nikolaenkova EB, Pervukhina NV, Naumov DY, Sheludyakova LA, Bushuev MB (2012) Copper(II) and copper(I) tetrafluoroborate complexes with 4-(3,5-diphenyl-1H-pyrazol-1-yl)-6-(piperidin-1-yl)pyrimidine (L): synthesis, structures and luminescence. Inorg Chim Acta 386:116–121

    Article  CAS  Google Scholar 

  25. Govindswamy P, Mozharivskyj YA, Kollipara MR (2004) Synthesis and characterization of cyclopentadienylruthenium(II) complexes containing N, N′-donor Schiff base ligands: crystal and molecular structure of [(5–C5H5)Ru(C5H4N-2-CH=N–C6H4–p-OCH3)(PPh3)]PF6. Polyhedron 23:1567–1572

    Article  Google Scholar 

  26. Garcia MH, Florindo P, Fatima M, Piedade M, Duarte MT, Robalo MP, Goovaerts E, Wenseleers WJ (2009) Synthesis and structural characterization of ruthenium(II) and iron(II) complexes containing 1,2-di-(thienyl)-ethene derived ligands as chromophores. Org Chem 694:433–445

    Article  CAS  Google Scholar 

  27. Wu F, Tong H, Wang K, Zhang X, Zhu X, Wong W-K (2016) Mononuclear copper(I) bromide complexes chelated with bis (pyrazol-1-ylmethyl)-pyridine ligands: structures, electronic properties and solid state photoluminescence. J Lumin 177:82–87

    Article  CAS  Google Scholar 

  28. Hanna JV, Boyd SE, Healy PC, Bowmaker GA, Skelton BW, White AH (2005) Structural and solid state 31P NMR studies of the four-coordinate copper(I) complexes [Cu(PPh3)3X] and [Cu(PPh3)3(CH3CN)]X. Dalton Trans 2547–2556

  29. Kia R, Mirkhani V, Harkema S, Hummel GJ (2007) Synthesis and characterization of the 1:1 adducts of copper(I) halides with bidentate N, N-bis(benzophenone)-1,2-diiminoethane Schiff base: crystal structures of [Cu(bz2en)2] [CuX2] (X = Br, I) complexes. Inorg Chim Acta 360:3369–3375

    Article  CAS  Google Scholar 

  30. Chen M-S, Hua Q, Bai Z-S, Okamura T, Zhi S, Wei-Yin S, Ueyama N (2010) Syntheses and characterization of inorganic–organic hybrids with 4-(isonicotinamido) phthalate and some divalent metal centers. Polyhedron 29:2454–2461

    Article  CAS  Google Scholar 

  31. Zu Y, Ma Y, Zhu J (2013) The counter anion effect of ion-type phosphorescent dye tris(4,7-diphenyl-1,10-phenanthroline)ruthenium(II) complexes as dopant for light-emitting diodes. J Lumin 137:198–203

    Article  Google Scholar 

  32. Sun W, Zhang Q, Qin L, Cheng Y, Xie Z, Lu C, Wang L (2010) Phosphorescent cuprous complexes with N, O ligands–synthesis, photoluminescence, and electro-luminescence. Eur J Inorg Chem 25:4009–4017

    Article  Google Scholar 

  33. Lavie-Cambot A, Cantuel M, Leydet Y, Jonusauskas G, Bassani DM, McClenaghana ND (2008) Improving the photophysical properties of copper(I) bis(phenanthroline) complexes. Coord Chem Rev 252:2572–2584

    Article  CAS  Google Scholar 

  34. Johansson Seechurn CC, Kitching MO, Colacot TJ, Snieckus V (2012) Angew Chem Int Ed 51:5062–5085

    Article  CAS  Google Scholar 

  35. Bolm C, Legros J, Le-Paih J, Zani L (2004) Iron-catalysed reactions in organic Synthesis. Chem Rev 104:6217–6254

    Article  CAS  Google Scholar 

  36. Naeimi H, Moradian M (2014) Thioether-based copper(I) Schiff base complexes as a catalyst for a direct and asymmetric A3-couping reaction. Tetrahedron Asymmetry 25:429–434

    Article  CAS  Google Scholar 

  37. Fazal A, Al-Fayez S, Abdel-Rahman LH, Seddigi ZS, Al-Arfaj AR, El AB, Dastageer M, Gondal MA, Fettouhi M (2009) Mixed-ligand complexes of copper(I) with diimines and phosphines: effective catalysts for the coupling of phenylacetylene with halobenzene. Polyhedron 28:4072–4076

    Article  CAS  Google Scholar 

  38. Patil NM, Kelkar AA, Nabi Z, Chaudhari RV (2003) Novel CuI/tributyl phosphine catalyst system for amination of aryl chlorides. Chem Commun 19:2460–2461

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Shivaji University, Kolhapur, MS, 416004, India

    S. S. Devkule & S. S. Chavan

Authors
  1. S. S. Devkule
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. S. Chavan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. S. Chavan.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Devkule, S.S., Chavan, S.S. Copper(I) complexes of 2-(benzen-1-yl)methyleneamino-3-aminomaleonitrile and triphenylphosphine ligands: synthesis, characterization, luminescence and catalytic properties. Transit Met Chem 42, 347–356 (2017). https://doi.org/10.1007/s11243-017-0138-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11243-017-0138-8

Keywords

Search

Navigation