Skip to main content
Log in

Crystal Structures, Optical Properties, and TD-DFT Study of a Zinc(II) Schiff-Base Complex Derived from Salicylaldehyde and N1-(3-aminopropyl)Propane-1,3-Diamine

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

A zinc(II) complex of the pentadentate Schiff base ligand 2,2′(((azanediylbis(propane-3,1-diyl))bis(azanylylidene))bis(methanylylidene))diphenol was synthesized by reaction of the ligand with Zn(OAc)2. Reaction of salicylaldehyde with N1-(3-aminopropyl)propane-1,3-diamine [HN(C3H6NH2)2] in absolute ethanol was used to prepare the ligand. Non-merohedrally twinned crystals of the complex were characterized by single-crystal XRD and found to be in the monoclinic system, space group P21/n, with the following lattice parameters: a = 14.6594(8) Å, b = 11.6908(7) Å, c = 23.2789(14) Å, and β = 105.520(3)°. Luminescent characteristics of this complex were investigated in the solid state. Computational study of the electronic properties of this complex with the aid of time-dependent density functional theory (TD-DFT) showed good agreement with experimental data and hence consolidated the assignment of the state as ligand centered charge transfer. This complex exhibits a strong fluorescence with a broad blue emission maximum centered at 442 nm.

Graphical Abstract

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.

Institutional subscriptions

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

Similar content being viewed by others

References

  1. Sinn E, Harris CM (1969) Coord Chem Rev 4:391

    Article  CAS  Google Scholar 

  2. Wilkinson SM, Sheedy TM, New EJ (2016) J Chem Edu 93:351

    Article  CAS  Google Scholar 

  3. Abu-Dief AM, Mohamed IMA (2015) J Basic Appl Sci 4:119

    Google Scholar 

  4. Charef N, Sebti F, Arrar L, Djarmouni M, Boussoualim N, Baghiani A, Khennouf S, Ourari A, AlDamen MA, Mubarak MS, Peters DG (2015) Polyhedron 85:450

    Article  CAS  Google Scholar 

  5. da Silva CM, da Silva DL, Modolo LV, Alves RB, de Resende MA, Martins CVB, de Fátima  (2011) J Adv Res 2:1

    Article  Google Scholar 

  6. Irena K, Luciano S (2013) Curr Med Chem 20:4609

    Article  Google Scholar 

  7. Matar SA, Talib WH, Mustafa MS, Mubarak MS, AlDamen MA (2015) Arab J Chem 8:850

    Article  CAS  Google Scholar 

  8. Chakraborty S, Bhattacharjee CR, Mondal P, Prasad SK, Rao DSS (2015) Dalton Trans 44:7477

    Article  CAS  Google Scholar 

  9. Vančo J, Trávníček Z, Kozák O, Boča R (2015) Int J Mol Sci 16:9520

    Article  Google Scholar 

  10. Terenzi A, Lauria A, Almerico AM, Barone G (2015) Dalton Trans 44:3527

    Article  CAS  Google Scholar 

  11. Gupta KC, Sutar AK (2008) Coord Chem Rev 252:1420

    Article  CAS  Google Scholar 

  12. Jussi S, Anssi H, Pekka P, Gösta B, Timo R, Juha A, Markku L (2001) ACS Symposium Series 785. American Chemical Society, Washington, pp 286–296

    Google Scholar 

  13. Roy P, Dhara K, Manassero M, Banerjee P (2009) Inorg Chim Acta 362:2927

    Article  CAS  Google Scholar 

  14. Jimenez-Sanchez A, Ortiz B, Ortiz Navarrete V, Farfan N, Santillan R (2015) Analyst 140:6031

    Article  CAS  Google Scholar 

  15. M-h Yan, T-r Li, Z-y Yang (2011) Inorg Chem Commun 14:463

    Article  Google Scholar 

  16. Hsieh WH, Wan C-F, Liao D-J, Wu A-T (2012) Tetrahedron Lett 53:5848

    Article  CAS  Google Scholar 

  17. Qian SS, Cheng XS, Ren JQ, You ZL, Zhu HL (2013) Russ J Coord Chem 39:836

    Article  CAS  Google Scholar 

  18. Abdel Aziz AA, Seda SH (2015) J Fluoresc 25:1711

    Article  CAS  Google Scholar 

  19. Juwhari HK, White WB (2012) Mater Lett 88:16

    Article  CAS  Google Scholar 

  20. Lee C-S Application of charge transfer complexes in organic optoelectronic devices. In: Light, energy and the environment, Canberra, 2014/12/02 2014. OSA Technical Digest (online). Optical Society of America, p DTu4C.2. doi:10.1364/SOLED.2014.DTu4C.2

  21. Goetz KP, Vermeulen D, Payne ME, Kloc C, McNeil LE, Jurchescu OD (2014) J Mater Chem C 2:3065

    Article  CAS  Google Scholar 

  22. AlDamen MA, Haddad SF (2012) Acta Cryst E 68:3314

    Article  Google Scholar 

  23. Sheldrick G (2008) A short history of SHELX. Acta Cryst A 64:112

    Article  CAS  Google Scholar 

  24. Bruker (2014) APEX2 and SADABS. Bruker AXS Inc., Madison

  25. Tirado-Rives J, Jorgensen WL (2008) J Chem Theory Comput 4:297

    Article  CAS  Google Scholar 

  26. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark MJ, Heyd J, Brothers EN, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam NJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09. Gaussian Inc, Wallingford

    Google Scholar 

  27. Stratmann RE, Scuseria GE, Frisch MJ (1998) J Chem Phys 109:8218

    Article  CAS  Google Scholar 

  28. Noel O’Boyle M, Vos JG (2005) GaussSum 1.0. Dublin City University, Dublin

    Google Scholar 

  29. Leonid S (2005–2014) Chemissian. 4.2.3 edn

  30. Al-Noaimi M, AlDamen MA (2012) Inorg Chim Acta 387:45

    Article  CAS  Google Scholar 

  31. Al-Noaimi M, Sunjuk M, El-khateeb M, Haddad SF, Haniyeh A, AlDamen M (2012) Polyhedron 42:66

    Article  CAS  Google Scholar 

  32. Baccouche A, Peigne B, Ibersiene F, Hammoutene D, Boutarfaia A, Boucekkine A, Feuvrie C, Maury O, Ledoux I, Le BH (2010) J Phys Chem A 114(116):5429–5438

    Article  CAS  Google Scholar 

  33. Craciun L, Jitaru I (2013) Sci Bull - Univ “Politeh” Bucharest 75:179

    CAS  Google Scholar 

  34. Hasenzahl S, Kaim W, Stahl T (1994) Inorg Chim Acta 225:23

    Article  CAS  Google Scholar 

  35. Liu X-Y, Han X, Zhang L-P, Tung C-H, Wu L-Z (2010) Phys Chem Chem Phys 12:13026

    Article  CAS  Google Scholar 

  36. Tan J, Li R, Li D, Zhang Q, Li S, Zhou H, Yang J, Wu J, Tian Y (2015) Dalton Trans 44:1473

    Article  CAS  Google Scholar 

  37. Yu T, Zhang K, Zhao Y, Yang C, Zhang H, Qian L, Fan D, Dong W, Chen L, Qiu Y (2008) Inorg Chim Acta 361:233

    Article  CAS  Google Scholar 

  38. Benedix R, Hennig H, Kunkely H, Vogler A (1990) Chem Phys Lett 175:483

    Article  CAS  Google Scholar 

  39. Ikeda S, Yamamoto S, Nozaki K, Ikeyama T, Azumi T, Burt JA, Crosby GA (1991) J Phys Chem 95:8538

    Article  CAS  Google Scholar 

  40. Leirer M, Knor G, Vogler A (2000) J Coord Chem 50:141

    Article  CAS  Google Scholar 

  41. Cai L-Z, Guo G-C, Fu M-L, Wang M-S, Chen W-T, Huang J-S (2006) Inorg Chim Acta 359:4483

    Article  CAS  Google Scholar 

  42. Xiao B, Hou H, Fan Y, Tang M (2007) Inorg Chem Commun 10:376

    Article  CAS  Google Scholar 

  43. Yang C, Wang M-S, Cai L-Z, Jiang X-M, Wu M-F, Guo G-C, Huang J-S (2010) Inorg Chem Commun 13:1021

    Article  CAS  Google Scholar 

  44. Das K, Jana A, Konar S, Chatterjee S, Mondal TK, Barik AK, Kar SK (2013) J Mol Struct 1048:98

    Article  CAS  Google Scholar 

  45. Zhang Y, Yu X, He H, Zhang J, Wang L (2014) Eur Phys J D 68:26

    Article  Google Scholar 

  46. Wang J-J, Zhang Y-J, Chen J, Zhang Y-H (2014) Inorg Chim Acta 411:30

    Article  CAS  Google Scholar 

  47. Tong YP, Jin Z, Lin YW (2015) J Struct Chem 56:406

    Article  CAS  Google Scholar 

  48. Nishal V, Singh D, Saini RK, Tanwar V, Kadyan S, Srivastava R, Kadyan PS (2015) Cogent Chem 1:1079291

    Article  Google Scholar 

  49. Basak S, Sen S, Banerjee S, Mitra S, Rosair G, Rodriguez MTG (2007) Polyhedron 26:5104

    Article  CAS  Google Scholar 

  50. Lan X, Mi W, Ji M, Hao C, Qiu J (2013) J Comput Theor Nanosci 10:2088

    Article  CAS  Google Scholar 

  51. Takeuchi T, Gray HB, Goddard WA (1994) J Am Chem Soc 116:9730

    Article  CAS  Google Scholar 

  52. Ye Q, Chen X-B, Song Y-M, Wang X-S, Zhang J, Xiong R-G, Fun H-K, You X-Z (2005) Inorg Chim Acta 358:1258

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Murad A. AlDamen or Dennis G. Peters.

Electronic Supplementary Material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 1723 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

AlDamen, M.A., Charef, N., Juwhari, H.K. et al. Crystal Structures, Optical Properties, and TD-DFT Study of a Zinc(II) Schiff-Base Complex Derived from Salicylaldehyde and N1-(3-aminopropyl)Propane-1,3-Diamine. J Chem Crystallogr 46, 411–420 (2016). https://doi.org/10.1007/s10870-016-0670-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-016-0670-y

Keywords

Navigation