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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 07: 1321 - 1326

DOI: https://doi.org/10.6023/cjoc201204033

Notes

Synthesis and Characterization of a Novel Frétchet Dendritic Phthalocyanine Zinc(Ⅱ): Tetra-{3,5-di-[3,5-di-(4-carboxylic benzyloxy) benzyloxy] benzyloxy} Phthalocyanine Zinc(Ⅱ)

  • He Dandan ,
  • Zhang Hong ,
  • Peng Yiru ,
  • Ma Dongdong ,
  • Wang Yuhua ,
  • Yang Hongqin ,
  • Chen Wanlin ,
  • Zhang Tiantian
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  • a College of Chemistry and Materials Science, Fujian Provincial Key Laboratory of Polymer Materials, Fujian Normal University, Fuzhou 350007, China;
    b Key Lab of Optoelectronic Science and Technology for Medicine of Ministry of Education, Fujian Normal University, Fuzhou 350007, China;
    c College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005

Received date: 2012-04-27

  Revised date: 2012-06-02

  Online published: 2012-06-06

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 60978071, 20604007), the Natural Science Foundation of Fujian Province (Nos. 2011J01029, 2010J01322), and the Scientific Research Fund of Ministry of Health (No. WKJ2008-2-61).

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Abstract

A novel Frétchet structural dendritic substituted photosensitizer, tetra-{3,5-di-[3,5-di- (4-carboxylic benzyloxy) benzyloxy] benzyloxy} zinc (Ⅱ) phthalocyanine 6, was synthesized by the following steps. Firstly, 3,5-di-(4-cyanobenzyloxy) benzyl alcohol (1) was obtained by reaction of 3,5-di-hydroxybenzyl alcohol with p-cyanobenzylbromide. Then, 3,5-di-(4-cyanobenzyloxy) benzyl bromide (2) was synthesized by the reaction of 1 with carbon tetrabromide in the presence of triphenylphosphine and tetrahydrofuran. Following, 2 reacted with 3,5-di-hydroxybenzyl alcohol to afford 3,5-di-[3,5-di-(4-cyanobenzyloxy) benzyloxy] benzyl alcohol (3). The fragment 4-{3,5-di-[3,5-di-(4-cyanobenzyloxy)benzyloxy]} phthalonitrile (4) was obtained by reaction of 3 with 4-nitrophthalonitrile. Tetra-{3,5-di-[3,5-di-(4-cyanobenzyloxy) benzyloxy] benzyloxy} zinc(Ⅱ) (5) was obtained by condensation of 4 with acetate zinc and 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) in n-pentanol. The tetra-{3,5-di-[3,5-di-(4-carboxylic benzyloxy) benzyloxy] benzyloxy} phthalocyanine zinc(Ⅱ) (6) was obtained by hydrolyzed 5 in NaOH. The structures of above compounds were characterized by a combination of methods including elemental analysis, 1H NMR, IR, ESI-MS and MALDI-TOF-MS. The photophysical properties of 5 and 6 were studied by UV/Vis, steady state and transient fluorescence spectrometry. The compound 6 is a kind of good performance of dendritic photosensitizer.

Key words： tetra-{3,5-di-[3,5-di-(4-carboxylic benzyloxy)benzyloxy] benzyloxy} zinc(Ⅱ) phthalocyanine; synthesis; characterization; frétchet dendritic

Cite this article

He Dandan , Zhang Hong , Peng Yiru , Ma Dongdong , Wang Yuhua , Yang Hongqin , Chen Wanlin , Zhang Tiantian . Synthesis and Characterization of a Novel Frétchet Dendritic Phthalocyanine Zinc(Ⅱ): Tetra-{3,5-di-[3,5-di-(4-carboxylic benzyloxy) benzyloxy] benzyloxy} Phthalocyanine Zinc(Ⅱ)[J]. Chinese Journal of Organic Chemistry, 2012 , 32(07) : 1321 -1326 . DOI: 10.6023/cjoc201204033

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