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Sonochemical Synthesis of a Nanocrystalline Tin(IV) Complex based on a Bulky Anthracene Carboxylate Ligand: Spectroscopic and Photophysical Properties

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Abstract

In order systematically investigate the effect of ligand with a large conjugated π-system on the structure and optical properties of tin complex, anthracene-9-carboxylic acid (L1) is selected as a primary ligand, and quinoline-2-carboxylic acid (L2) used as second ligand to incorporate with anthracene-9-carboxylic acid to construct a new tin(IV)-carboxylate coordination complex under thermal gradient condition. Prepared complex was fully characterized based on its 1H and 13C NMR, IR and UV spectra and elemental analysis. The molecular structure of complex was determined by single-crystal X-ray analysis. The nanocrystalline complexes of the prepared complex were successfully obtained at 30, 50 and 60 °C by a facile sonochemical route. The new nanocrystalline complexes were characterized by scanning electron microscopy, X-ray powder diffraction, IR spectroscopy and elemental analysis. The photoluminescence properties of the nanocrystalline complexes and crystalline bulk complex in the solid-state indicated that the size of the complex particles has a remarkable effect on the optical properties of it. Absorption and emission peaks of the nanocrystalline complexes blue shifted significantly in comparison with those of in the single-crystal form. Application of the prepared complex in fabrication of an organic light-emitting diode has been demonstrated. The current–voltage (I–V) characteristics and the electroluminescence (EL) properties of the complex have been investigated. The EL of the compound exhibits green emission at 552 nm.

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References

  1. K. Kuriki, Y. Koike, Y. Okamoto, Chem Rev 102, 2347 (2002)

    Article  CAS  Google Scholar 

  2. S. Faulkner, J.L. Matthews, Comprehensive coordination chemistry II (Elsevier, Oxford, 2004)

    Google Scholar 

  3. J. Thompson, R.I.R. Blyth, G. Gigli, R. Cingolani, Adv Funct Mater 14, 979 (2004)

    Article  CAS  Google Scholar 

  4. S. Faulkner, S.J.A. Pope, B.P. Burton-Pye, Appl Spectrosc Rev 40, 1 (2005)

    Article  CAS  Google Scholar 

  5. W. Su, M. Hong, J. Weng, R. Cao, S. Lu, Angew Chem Int Ed 39, 2911 (2000)

    Article  CAS  Google Scholar 

  6. Q.M. Wang, T.C.W. Mak, J Am Chem Soc 123, 7594 (2001)

    Article  CAS  Google Scholar 

  7. Z. Mao, H.Y. Chao, Z. Hui, C.M. Che, W.F. Fu, K.K. Cheung, N. Zhu, Chem Eur J 9, 2885 (2003)

    Article  CAS  Google Scholar 

  8. C.S. Campos-Fernandez, B.L. Schottel, H.T. Chifotides, J.K. Bera, J. Bacsa, J.M. Koomen, D.H. Russell, K.R. Dunbar, J Am Chem Soc 127, 12909 (2006)

    Article  Google Scholar 

  9. X.H. Bu, M.L. Tong, H.C. Chang, S. Kitagawa, S.R. Batten, Angew Chem Int Ed 43, 192 (2004)

    Article  CAS  Google Scholar 

  10. S. Hiraoka, K. Harano, M. Shiro, Y. Ozawa, N. Yasuda, K. Toriumi, M. Shionoya, Angew Chem Int Ed 45, 6488 (2006)

    Article  CAS  Google Scholar 

  11. C.S. Liu, X.S. Shi, J.R. Li, J.J. Wang, X.H. Bu, Cryst Growth Des 6, 656 (2006)

    Article  Google Scholar 

  12. R.Q. Zou, C.S. Liu, X.S. Shi, X.H. Bu, J. Ribas, CrystEngComm 7, 722 (2005)

    Article  CAS  Google Scholar 

  13. X.H. Bu, M.-L. Tong, Y.B. Xie, J.R. Li, H.C. Chang, S. Kitagawa, J. Ribas, Inorg Chem 44, 9837 (2005)

    Article  CAS  Google Scholar 

  14. A.J. Eastwood, A.E.A. Contoret, S.R. Farrar, S. Fowler, S.M. Kelly, S.M. Khan, J.E. Nicholls, M. O’Neill, Synth Met 121, 1659 (2001)

    Article  CAS  Google Scholar 

  15. Bernardo MA, Pina F, Escuder B, Garcia-España E, Godino-Salido ML, Latorre J, Luis SV, Ramírez JA, Soriano C (1999) J Chem Soc Dalton Trans, p 915

  16. B. Bag, P.K. Bharadwaj, J. Phys. Chem. B. 109, 4377 (2005)

    Article  CAS  Google Scholar 

  17. K. Kubo, A. Mori, J Mater Chem 15, 2902 (2005)

    Article  CAS  Google Scholar 

  18. A. Tamayo, C. Lodeiro, L. Escriche, J. Casabó, B. Covelo, P. González, Inorg Chem 44, 8105 (2005)

    Article  CAS  Google Scholar 

  19. S. Furukawa, S. Kitagawa, Inorg Chem 43, 6464 (2004)

    Article  CAS  Google Scholar 

  20. C.S. Liu, J.J. Wang, L.F. Yan, Z. Chang, X.H. Bu, E.C. Sanudo, J. Ribas, Inorg Chem 46, 6299 (2007)

    Article  CAS  Google Scholar 

  21. H.B. Michaelson, J Appl Phys 48, 4729 (1977)

    Article  CAS  Google Scholar 

  22. X.T. Tao, M. Shimomura, H. Suzuki, S. Miyata, H. Sasabe, Appl Phys Lett 76, 3522 (2000)

    Article  CAS  Google Scholar 

  23. K. Akhbari, A. Morsali, P. Retailleau, Ultrason Sonochem 20, 1428 (2013)

    Article  CAS  Google Scholar 

  24. S. Taheri, A. Mojidov, A. Morsali, Z. Anorg, Allgery Chem 633, 1949 (2007)

    CAS  Google Scholar 

  25. A. Aslani, A. Morsali, M. Zeller, Solid State Sci 10, 1591 (2008)

    Article  CAS  Google Scholar 

  26. H. Shi, L. Qi, J. Ma, H. Cheng, J Am Chem Soc 125, 3450 (2003)

    Article  CAS  Google Scholar 

  27. H. Zhang, D.R. Yang, D.S. Li, X.Y. Ma, S.Z. Li, D.L. Que, Cryst Growth Des 5, 547 (2005)

    Article  CAS  Google Scholar 

  28. D.B. Kuang, A.W. Xu, Y.P. Fang, H.Q. Liu, C. Frommen, D. Fenske, Adv Mater 15, 1747 (2003)

    Article  CAS  Google Scholar 

  29. M.S. Yeh, Y.S. Yang, Y.P. Lee, H.F. Lee, Y.H. Yeh, C.S. Yeh, J Phys Chem B 103, 6851 (1999)

    Article  CAS  Google Scholar 

  30. J.F. Xu, W. Ji, J.Y. Lin, S.H. Tang, Y.W. Du, Appl Phys A 66, 639 (1998)

    Article  CAS  Google Scholar 

  31. E. Shahriari, W.M. Mat, Yunus. Braz J Phys 40, 256 (2010)

    Article  CAS  Google Scholar 

  32. Y.H. Kim, D.K. Lee, B.G. Jo, J.H. Jeong, Y.S. Kang, Colloid Surf A 284, 364 (2006)

    Google Scholar 

  33. J. Wan, X. Jiang, H. Li, K. Chen, J Mater Chem 22, 13500 (2012)

    Article  CAS  Google Scholar 

  34. A.A. Ponce, K.J. Klabunde, J Mol Catal A 225, 1 (2005)

    Article  CAS  Google Scholar 

  35. N. Iranpoor, H. Firouzabadi, A. Safavi, S. Motevalli, M.M. Doroodmand, Appl Organometal Chem 26, 417 (2012)

    Article  CAS  Google Scholar 

  36. S.K. Haram, A.R. Mahadeshwar, S.G. Dixit, J Phys Chem 100, 5868 (1996)

    Article  CAS  Google Scholar 

  37. K. Kowlgi, U. Lafont, M. Rappolt, G. Koper, J Colloid Interface Sci 372, 16 (2012)

    Article  CAS  Google Scholar 

  38. M.M. Amini, E. Najafi, P.H. Poor, P. Karami, B. Mohammadi, A. Olyaei, S.W. Ng, J Inorg Organomet Polym 25, 1137 (2015)

    Article  CAS  Google Scholar 

  39. D.D. Perrin, W.L.F. Armarego, D.R. Perrin, Purification of laboratory chemicals, 2nd edn. (Springer, New York, 1980)

    Google Scholar 

  40. SMART (2005) APEX2, version 2.1. Madison, WI: Bruker AXS Inc

  41. G.M. Sheldrich, SADABS (University of Gottingen, Germany, 2005)

    Google Scholar 

  42. Sheldrich GM (1997) SHELXS-97, University of Gottingen, Germany

  43. APEX2 and SAINT (2008) Bruker AXS Inc., Madison, Wisconsin, USA

  44. E. Najafi, M.M. Amini, E. Mohajerani, M. Janghouri, H. Razavi, H.R. Khavasi, Inorg Chim Acta 399, 119 (2013)

    Article  CAS  Google Scholar 

  45. E. Najafi, M.M. Amini, H.R. Khavasi, S.W. Ng, J Organomet Chem 749, 370 (2014)

    Article  CAS  Google Scholar 

  46. K.S. Suslick, S.B. Choe, A.A. Cichowlas, M.W. Grinstaff, Nature 353, 414 (1991)

    Article  CAS  Google Scholar 

  47. J. Ouyang, Y. Xu, L.E.J. Khoo, J Organomet Chem 561, 143 (1998)

    Article  CAS  Google Scholar 

  48. G.B. Deacon, R.J. Phillips, Coord Chem Rev 33, 227 (1980)

    Article  CAS  Google Scholar 

  49. E. Najafi, M.M. Amini, S.W. Ng, Acta Cryst E 68, m732 (2012)

    Article  CAS  Google Scholar 

  50. M.M. Amini, A.R. Azadmeher, H.R. Khavasi, S.W. Ng, J Organomet Chem 692, 3922 (2007)

    Article  CAS  Google Scholar 

  51. E. Najafi, M.M. Amini, L. Masoomi, S.S. HosseinyDavarani, M. Janghouri, E. Mohajerani, S.W. Ng, J Coord Chem 66, 2712 (2013)

    Article  CAS  Google Scholar 

  52. J.M. Lehn, Science 295, 2400 (2002)

    Article  CAS  Google Scholar 

  53. B. Moulton, M.J. Zaworotko, Chem Rev 101, 1629 (2001)

    Article  CAS  Google Scholar 

  54. C.B. Aakeröy, D.J. Salmon, CrystEngComm 7, 439 (2005)

    Article  Google Scholar 

  55. M. Wegner, J. Bernstein, Angew Chem Int Ed 45, 7966 (2006)

    Article  Google Scholar 

  56. M.W. Hosseini, Acc Chem Res 38, 313 (2005)

    Article  CAS  Google Scholar 

  57. Goldberg I (2005) Chem Commun, p 1243

  58. C.J. Kuehl, F.M. Tabellin, A.M. Arif, P. Stang, J Organometallics 20, 1956 (2001)

    Article  CAS  Google Scholar 

  59. D. Braga, F. Grepioni, Acc Chem Res 33, 601 (2000)

    Article  CAS  Google Scholar 

  60. D. Braga, F. Grepioni, G.R. Desiraju, Chem Rev 98, 1375 (1998)

    Article  CAS  Google Scholar 

  61. M. Munakata, L.P. Wu, M. Yamamoto, T. Kuroda-Sowa, M. Maekawa, J Am Chem Soc 118, 3117 (1996)

    Article  CAS  Google Scholar 

  62. G.R. Desiraju, Curr Opin Solid State Mater Sci 2, 451 (1997)

    Article  CAS  Google Scholar 

  63. T.N. Guru Row, Coord Chem Rev 183, 81 (1999)

    Article  Google Scholar 

  64. M. Nishio, Y. Umezawa, K. Honda, S. Tsuboyama, H. Suezawa, CrystEngComm 11, 1757 (2009)

    Article  CAS  Google Scholar 

  65. M. Nishio, M. Hirota, Y. Umezawa, The CH/π interaction. Evidence, nature, and consequences (Wiley-VCH, New York, 1998)

    Google Scholar 

  66. M. Nishio, Cryst Eng Commun 6, 130 (2004)

    Article  CAS  Google Scholar 

  67. Y. Umezawa, S. Tsuboyama, K. Honda, J. Uzawa, M. Nishio, Bull Chem Soc Jpn 71, 1207 (1998)

    Article  CAS  Google Scholar 

  68. K.A. Hirsch, S.R. Wilson, J.S. Moore, Chem Eur J 3, 765 (1997)

    Article  CAS  Google Scholar 

  69. D.B. Amabilino, J.F. Stoddart, Chem Rev 95, 2725 (1995)

    Article  CAS  Google Scholar 

  70. J.H. He, T.H. Wu, C.L. Hsin, K.M. Li, L.J. Chen, Y.L. Chueh, L.J. Chou, Z.L. Wang, Small 2, 116 (2006)

    Article  CAS  Google Scholar 

  71. J.J. Wang, C.S. Liu, T.L. Hu, Z. Chang, C.Y. Li, L.F. Yan, P.Q. Chen, X.H. Bu, Q. Wu, L.J. Zhao, Z. Wang, X.Z. Zhang, Cryst Eng Commun 10, 681 (2008)

    Article  Google Scholar 

  72. G.R. Choppin, D.R. Peterman, Coord Chem Rev 174, 283 (1998)

    Article  CAS  Google Scholar 

  73. X. Pang, H. Sun, Y. Zhang, Q. Shen, H. Zhang, Eur J Inorg Chem 8, 1487 (2005)

    Article  Google Scholar 

  74. V.W.W. Yam, K.K.W. Lo, Chem Soc Rev 28, 323 (1999)

    Article  CAS  Google Scholar 

  75. S.L. Zheng, J.H. Yang, X.L. Yu, X.M. Chen, W.T. Wong, Inorg Chem 43, 830 (2004)

    Article  CAS  Google Scholar 

  76. X.L. Wang, C. Qin, E.B. Wang, Z.M. Su, Chem Eur J 12, 2680 (2006)

    Article  CAS  Google Scholar 

  77. P. Gupta, M. Ramrakhiani, Influence of the particle size on the optical properties of CdSe nanoparticles. Open Nanosci J 3, 15 (2009)

    Article  CAS  Google Scholar 

  78. L.A. Moreno, J Vis Exp 63, e3066 (2012)

    Google Scholar 

  79. B. Ma, B.J. Kim, L. Deng, D. Poulsen, M.E. Thompson, J. Frechet, Macromolecules 40, 8156 (2007)

    Article  CAS  Google Scholar 

  80. J. Yang, K. Gordon, Chem Phys Lett 385, 481 (2004)

    Article  CAS  Google Scholar 

  81. S. Chang, C. Fan, C. Lai, Y. Chao, S. Hu, Surf Coat Technol 200, 3289 (2006)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Science and Research Campus, Islamic Azad University, Poonak, Tehran, Iran

    Merat Hodaie & Mirabdullah Seyed Sadjadi

  2. Department of Chemistry, Shahid Beheshti University G.C., Tehran, 1983963113, Iran

    Mostafa M. Amini

  3. Department of Chemistry, Payame Noor University (PNU), Tehran, 19395-3697, Iran

    Ezzatollah Najafi

  4. Department of Chemistry, University of Malaya, 50603, Kuala Lumpur, Malaysia

    Seik Weng Ng

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  1. Merat Hodaie
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  2. Mirabdullah Seyed Sadjadi
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  3. Mostafa M. Amini
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Correspondence to Mostafa M. Amini.

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10904_2016_344_MOESM1_ESM.docx

The crystallographic data for 1 has been deposited with Cambridge Crystallographic Data Center (CCDC) as supplementary publication number CCDC1002237. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam. ac.uk/data-request/cif.. Supplementary material 1 (DOCX 213 kb)

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Hodaie, M., Sadjadi, M.S., Amini, M.M. et al. Sonochemical Synthesis of a Nanocrystalline Tin(IV) Complex based on a Bulky Anthracene Carboxylate Ligand: Spectroscopic and Photophysical Properties. J Inorg Organomet Polym 26, 500–511 (2016). https://doi.org/10.1007/s10904-016-0344-4

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