研究简报

新型不对称酞菁锌的合成和表征

  • 俞孝伟 ,
  • 詹传郎 ,
  • 黄彦
展开
  • a 南京工业大学化学化工学院 材料化学工程国家重点实验室 南京 210009;
    b 中国科学院化学研究所 北京分子科学国家实验室 中国科学院光化学重点实验室 北京 100190

收稿日期: 2011-09-29

  修回日期: 2011-11-25

  网络出版日期: 2012-04-24

基金资助

国家自然科学基金(No. 20973182)资助项目.

Synthesis and Characterization of New Asymmetrical Phthalocyanine Zinc

  • Yu Xiaowei ,
  • Zhan Chuanlang ,
  • Huang Yan
Expand
  • a State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing 210009;
    b Beijing National Laboratory for Molecular Sciences (BNLMS), Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190

Received date: 2011-09-29

  Revised date: 2011-11-25

  Online published: 2012-04-24

Supported by

Project supported by the National Natural Science Foundation of China (No. 20973182).

摘要

以4-硝基邻苯二甲腈为主要原料, 合成了2(3),9(10),16(17),23(24)-四-(正庚酰胺基)-酞菁锌、2(3),9(10),16(17),23(24)-四-(甲氧基)-酞菁锌、2(3),9(10),16(17),23(24)-四-(对叔丁基苯氧基)-酞菁锌和2(3),9(10),16(17),23(24)-四-(苯氧基)-酞菁锌等4 种对称型酞菁. 在此基础上, 选取4-对叔丁基苯氧基邻苯二甲腈为前驱体, 采用概率法合成了含有氨基、羧基的2 种不对称酞菁锌(A3B).

本文引用格式

俞孝伟 , 詹传郎 , 黄彦 . 新型不对称酞菁锌的合成和表征[J]. 有机化学, 2012 , 32(04) : 770 -775 . DOI: 10.6023/cjoc1109291

Abstract

Four kinds of symmetrical phthalocyanine zincs (PCZn) 2(3),9(10),16(17),23(24)-(tetraheptanylcarbonyl amino)-phthalocyanine zinc, 2(3),9(10),16(17),23(24)-tetramethoxy-phthalocyanine zinc, 2(3),9(10),16(17),23(24)-tetra-(4- tert-butylphenoxyl)-phthalocyanine zinc, and 2(3),9(10),16(17),23(24)-tetraphenoxyl-phthalocyanine zinc were synthesized from 4-nitro-phthalonitrile. Moreover, the 4-(4-tert-butylphenoxyl)phthalonitrile was employed as a precursor in the synthesis of two kinds of asymmetrical PCZn (A3B) containing either amino- or carboxyl-group by probability method.

参考文献

[1] Mack, J.; Kobayashi, N. Chem. Rev. 2011, 2, 281.

[2] Claessens, C. G.; Blau, W. J.; Cook, M.; Hanack, M.; Nolte, R. J. M.; Torres, T.; Wohrle, D. Monatsh. Chem. 2001, 132(1), 3.

[3] Zhao, H.-L.; Yao, K.-S. Chem. Ind. Eng. Prog. 2008, 27, 1887 (in Chinese).(赵海丽, 姚开胜, 化工进展, 2008, 27, 1887.)

[4] Wang, B.-R. Organic Syntheses and Reactions, Science Press, Beijing, 1985, pp. 810~817 (in Chinese). (王葆仁, 有机合成反应, 科学出版社, 北京, 1985, pp. 810~ 817.)  

[5] Xie, W.-W.; Xu, H.-T.; Gan, C.-S.; Pan, Z.-X.; Yan, T.-T.; Peng, B.-X. Chin. J. Chem. Phys. 2003, 16, 491.

[6] Gao, J. S.; Cheng, C. W.; Zhou, X. C.; Li, Y. Y.; Xu, X. Q.; Du, X. G.; Zhang, H. Q. J. Colloid Interface Sci. 2010, 342, 225.  

[7] Baugh, S. D. P.; Yang, Z. W.; Leung, D. K.; Wilson, D. M.; Breslow, R. J. Am. Chem. Soc. 2001, 123, 12488.  

[8] Brewis, M.; Clarkson, G. J.; Humberstone, P.; Makhseed, S.; McKeown, N. B. Chem. Eur. J. 1998, 4, 1633.

[9] Tararykina, T. V.; Maizlish, V. E.; Galanin, N. E.; Shaposhnikov, G. P.; Bykova, V. V.; Usol'tseva, N. V. Russ. J. Org. Chem. 2007, 43, 1719.

[10] Zhang, X.-F.; Xu, H.-J. Chem. J. Chin. Univ. 1994, 15, 917 (in Chinese). (张先付, 许慧君, 高等学校化学学报, 1994, 15, 917.)

[11] Leznoff, C. C.; Hu, M.; Nolan, J. M. Chem. Commun. 1996, 1245.

[12] Tomoda, H.; Saito, S.; Ogawa, S.; Shiraishi, S. Chem. Lett. 1980, 1277.

[13] Kliesch, H.; Weitemeyer, A.; Muller, S.; Wohrle, D. Liebigs Ann. 1995, 1269

[14] Qiu, L.; Shen, Y.-J.; Xu, H.-J.; Yuan, P.; Xia, Z.-J.; Zou, Y.-H. Acta Chim. Sinica 1997, 55, 37 (in Chinese). (邱玲, 沈玉全, 许慧君, 袁平, 夏宗矩, 邹英华, 化学学报, 1997, 55, 37.)

[15] Nie, J.-T.; Duan, W.-B.; Yang, S.-L.; Chen, N.-S. Chin. J. Inorg. Chem. 1996, 9, 246 (in Chinese). (聂静涛, 段武彪, 杨素苓, 陈耐生, 无机化学学报, 1996, 9, 246.)

[16] Hu, M. G.; Brasseur, N.; Yildiz, S. Z.; Lier, J. E.; Leznoff, C. C. J. Med. Chem. 1998, 41, 1789.  

[17] Tomoda, H.; Saito, S.; Shinsaku, S. Chem. Lett. 1983, 313.

[18] Sibrian-Vazquez, M.; Ortiz, J.; Nesterova, I. V.; Femandez-Lazaro, F.; Sastre-Santos, A.; Soper, S. A.; Vicente, M. G. H. Bioconjugate Chem. 2007, 18, 410.  

[19] Alzeer, J.; Vummidi, B. R.; Roth, P. J. C.; Luedtke, N. W. Angew. Chem., Int. Ed. 2009, 48, 9362.  

[20] Kudrevich, S. V.; Ali, H.; Vanliter, J. E. J. Chem. Soc. 1994, 2767.  

[21] Mori, S.; Nagata, M.; Nakahata, Y.; Yasuta, K.; Goto, R.; Kimura, M.; Taya, M. J. Am. Chem. Soc. 2010, 132, 4054.  

[22] Walter, M. G.; Rudine, A. B.; Wamser, C. C. J. Porphyrins Phthalocyanines 2010, 14, 759.  
文章导航

/