Citation: BAI Ming, ZHANG Yan, WAN Pei-Hong, ZHANG Chong-Xi. Six Phthalocyaninato Zinc(Ⅱ) Complexes:Synthesis via Cross-Condensation of Two Phthalonitriles, Spectroscopy and Electrochemistry[J]. Chinese Journal of Inorganic Chemistry, ;2014, (2): 371-378. doi: 10.11862/CJIC.2014.029 shu

Six Phthalocyaninato Zinc(Ⅱ) Complexes:Synthesis via Cross-Condensation of Two Phthalonitriles, Spectroscopy and Electrochemistry

  • Corresponding author: BAI Ming, 
  • Received Date: 7 June 2013
    Available Online: 2 September 2013

    Fund Project:

  • Cross-condensation of two different phthalonitriles, namely 4,5-bis[(4-methyloxycarbonyl)phenoxy]phthalonitrile (1) and 4-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}phthalonitrile(2), in the presence of Zn(OAc)2·2H2Oand 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) followed by transesterification in refluxing n-pentanol afforded six phthalocyaninato zinc(Ⅱ) complexes modulated with different numbers of pentyloxycarbonyl and/or triethylene glycol monomethyl ether groups. Simple silica-gel column chromatography leads to the successful separation of all these six compounds, namely Zn[Pc(BP)4](3), Zn[Pc(BP)3(TEG)](4), Zn[Pc(BP)2(TEG)2]-opp(5), Zn[Pc(BP)2(TEG)2]-adj(6), Zn[Pc(BP)(TEG)3](7), and Zn[Pc(TEG)4](8). In addition, the six complexes have been characterized with elemental analysis, MALDI-TOFmass, UV-Vis spectroscopy, 1H NMR, and 2D COSYspectroscopy. The electrochemical properties have also been investigated.
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    1. [1]

      [1] Lever A B P, Leznoff C C Ed. Phthalocyanine: Properties and Applications: Vols. 1-4. New York: VCH Publishers, 1989-1996.

    2. [2]

      [2] McKeown N B. Phthalocyanines Materials: Synthesis, Structure and Function. New York: Cambridge University Press, 1998.

    3. [3]

      [3] Kadish K M, Smith K M, Guilard R Ed. The Porphyrin Handbook: Vol. 19. San Diego, CA: Academic Press, 2003.

    4. [4]

      [4] Jiang J Ed. Functional Phthalocyanine Molecular Materials. Berlin: Springer, 2010.

    5. [5]

      [5] Mack J, Kobayashi N. Chem. Rev., 2011,111:281-321

    6. [6]

      [6] de la Torre G, Claessens C G, Torres T. Eur. J. Org. Chem., 2000:2821-2830

    7. [7]

      [7] McKeown N B, Chambrier I, Cook M J. Perkin Trans., 1990: 1169-1177

    8. [8]

      [8] Kobayashi N, Kondo R, Nakajima S, et al. J. Am. Chem. Soc., 1990,112:9640-9641

    9. [9]

      [9] Kobayashi N, Ishizaki T, Ishii K, et al. J. Am. Chem. Soc., 1999,121:9096-9110

    10. [10]

      [10] Leznoff C C, Svirskay P I. Angew. Chem. Int. Ed., 1978,17: 947-947

    11. [11]

      [11] Hirth A, Sobbi A K, Whrle D. J. Porphyrins Phthalocyanines, 1997,1:275-279

    12. [12]

      [12] Kobayashi N, Miwa H, Nemykin V N. J. Am. Chem. Soc., 2002,124:8007-8020

    13. [13]

      [13] Sekellariou E G, Montalban A G, Meunier H G, et al. Inorg. Chem. 2002,41:2182-2187

    14. [14]

      [14] Donzello M P, Ercolani C, Gaberkorn A A, et al. Chem. Eur. J., 2003,9:4009-4024

    15. [15]

      [15] Luo Q, Chen B, Wang M, et al. Adv. Funct. Mater., 2003, 13:233-239

    16. [16]

      [16] Miwa H, Ishii K, Kobayashi N. Chem. Eur. J., 2004,10: 4422-4435

    17. [17]

      [17] Ishii K, Itoya H, Miwa H, et al. Chem. Commun., 2005: 4586-4588

    18. [18]

      [18] Ishii K, Itoya H, Miwa H, et al. J. Phys. Chem. A, 2005, 109:5781-5787

    19. [19]

      [19] Aoudia M, Cheng G, Kennedy V O, et al. J. Am. Chem. Soc., 1997,119:6029-6039

    20. [20]

      [20] Kobayashi N, Mack J, Ishii K, et al. Inorg. Chem., 2002,41: 5350-5363

    21. [21]

      [21] Haas M, Liu S L, Neels A, et al. Eur. J. Org. Chem., 2006: 5467-5478

    22. [22]

      [22] Li R, Jiang J, Bian Y. J. Porphyrins Phthalocyanines, 2010,14:421-437

    23. [23]

      [23] Clarkson G J, McKeown N B, Treacher K E. Perkin Trans. 1,1995,14:1817-1823

    24. [24]

      [24] Nemykin V N, Kobayashi N, Nonomura T, et al. Chem. Lett., 2000:184-185

    25. [25]

      [25] Youssef T E, OFlaherty S, Blau W, et al. Eur. J. Org. Chem., 2004:101-108

    26. [26]

      [26] Fukuda T, Homma S, Kobayashi N. Chem. Eur. J., 2005,11: 5205-5216

    27. [27]

      [27] Sakamoto K, Kato T, Cook M J. J. Porphyrins Phthalocyanines, 2001,5:742-750

    28. [28]

      [28] Sakamoto K, Kato T, Kawaguchi T, et al. J. Photochem. Photobiol., A, 2002,153:245-253

    29. [29]

      [29] Galanin N E, Shaposhnikov G P. Russ. J. Org. Chem. (Engl. Transl.), 2009,45:681-686

    30. [30]

      [30] Sheng N, Zhang Y, Xu H, et al. Eur. J. Inorg. Chem., 2007: 3268-3275

    31. [31]

      [31] Bai M, Lo P C, Ye J, et al. Org. Biomol. Chem., 2011,9: 7028-7032

    32. [32]

      [32] Bai M, Zhang Y, Song R, et al. Dyes and Pigments, 2013,97:469-474

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