具有Frétchet 树枝结构的新型酞菁锌(Ⅱ)配合物:四-{3,5-二-[3,5-二-(4-羧基苯甲氧基)苯甲氧基]-苯甲氧基}酞菁锌(Ⅱ)的合成与表征

doi:10.6023/cjoc201204033

有机化学 ›› 2012, Vol. 32 ›› Issue (07): 1321-1326.DOI: 10.6023/cjoc201204033 上一篇下一篇

研究简报

具有Frétchet 树枝结构的新型酞菁锌(Ⅱ)配合物:四-{3,5-二-[3,5-二-(4-羧基苯甲氧基)苯甲氧基]-苯甲氧基}酞菁锌(Ⅱ)的合成与表征

贺丹丹^a, 张宏^a,c, 彭亦如^a, 马冬冬^a, 王瑜华^b, 杨洪钦^b, 陈婉玲^a, 张甜甜^a

a 福建师范大学化学与材料学院,福建省高分子材料重点实验室福建福州350007;
b 福建师范大学医学光电科学与技术教育部重点实验室福建福州 350007;
c 厦门大学化学化工学院福建厦门 361005

收稿日期:2012-04-27 修回日期:2012-06-02 发布日期:2012-06-06
通讯作者: 彭亦如 E-mail:yirupeng@fjnu.edu.cn
基金资助:
国家自然科学基金(Nos. 60978071, 20604007);福建省自然科学基金(Nos. 2011J01029, 2010J01322)和卫生部科学研究基金(No. WKJ2008-2-61)资助项目

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^a, Zhang Hong^a,c, Peng Yiru^a, Ma Dongdong^a, Wang Yuhua^b, Yang Hongqin^b, Chen Wanlin^a, Zhang Tiantian^a

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:2012-04-27 Revised:2012-06-02 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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摘要/Abstract

报道了一种新型Frétchet 树枝配体取代酞菁锌(II)配合物:四-{3,5-二-[3,5-二-(4-羧基苯甲氧基)苯甲氧基]-苯甲氧基}锌酞菁(II)的合成与表征。首先将对氰基苄溴与3,5-二羟基苯甲醇通过Frétchet 反应合成3,5-[二-(4-氰基苯甲氧基)]苯甲醇1,1 与四溴化碳和三苯基膦在四氢呋喃中反应合成3,5-二-(4-氰基苯甲氧基)苄溴2,2 与3,5-二羟基苯甲醇反应合成3,5-二-[3,5-二-(4-氰基苯甲氧基)苯甲氧基]苯甲醇3,接着,3 与4-硝基邻苯二甲腈合成“前驱物”四-{3,5-[二-(4-氰基苯甲氧基)]}苯甲氧基邻苯二甲腈4,然后以1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)为催化剂,醋酸锌为模板剂,4 通过缩聚反应合成氰基端基的Frétchet树枝配体取代酞菁锌四-{3,5-二-[3,5-二-(4-氰基苯甲氧基)苯甲氧基]-苯甲氧基}锌酞菁配合物5,最后,5 的氰基端基在NaOH 溶液中水解为相应的以羧基端基Frétchet 树枝配体取代酞菁锌:四-{3,5-二-[3,5-二-(4-羧基苯甲氧基)苯甲氧基]-苯甲氧基}锌(Ⅱ)酞菁6。采用元素分析、IR、¹H NMR、ESI-MS 和MALDI-TOF-MS 表征所有化合物的结构,通过UV/vis,稳态和瞬态荧光光谱法研究了5 和6 的光物理性质。5 和6 是一类性能较好的树枝状酞菁光敏剂。

关键词: 四-{3,5-二-[3,5-二-(4-羧基苯甲氧基)苯甲氧基]-苯甲氧基}酞菁锌(Ⅱ), 合成, 表征, Frétchet 树枝

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

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贺丹丹, 张宏, 彭亦如, 马冬冬, 王瑜华, 杨洪钦, 陈婉玲, 张甜甜. 具有Frétchet 树枝结构的新型酞菁锌(Ⅱ)配合物:四-{3,5-二-[3,5-二-(4-羧基苯甲氧基)苯甲氧基]-苯甲氧基}酞菁锌(Ⅱ)的合成与表征[J]. 有机化学, 2012, 32(07): 1321-1326.

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]. Chin. J. Org. Chem., 2012, 32(07): 1321-1326.

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具有Frétchet 树枝结构的新型酞菁锌(Ⅱ)配合物:四-{3,5-二-[3,5-二-(4-羧基苯甲氧基)苯甲氧基]-苯甲氧基}酞菁锌(Ⅱ)的合成与表征

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)

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