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近红外水溶性不对称吲哚方酸菁染料的合成
  • ISSN号:0567-7351
  • 期刊名称:《化学学报》
  • 时间:0
  • 分类:O626[理学—有机化学;理学—化学]
  • 作者机构:[1]大连理工大学精细化工国家重点实验室,大连116012, [2]齐齐哈尔大学化学与化学工程学院,齐齐哈尔161006
  • 相关基金:国家自然科学基金(No.20725621); 973计划项目(No.2009CB724706)资助项目
中文摘要:

以吲哚啉季铵盐为原料,分别采用两步法和固相法合成了3种水溶性不对称吲哚方酸菁染料.两步法为将不同N-烷基取代的2,3,3-三甲基-3H-吲哚-5-磺酸季铵盐与方酸反应,再与另一种吲哚啉季铵盐反应制备不对称菁染料.固相法是用对氨基苯甲酸做桥连物,将方酸化学键连到高分子固相载体聚乙二醇上,然后与吲哚啉季铵盐杂环母核缩合制得带有固相高分子载体的半菁,再与另一吲哚啉季铵盐杂环母核反应切掉载体,合成不对称菁染料.产品用C-18反相柱进行分离提纯,通过核磁共振氢谱和质谱对产品结构进行了表征,测试了产品的光谱性能.比较而言,固相法合成不对称染料效果更好,产率接近传统两步法的二倍,是一种更适合的合成水溶性不对称吲哚方酸菁染料的方法.

英文摘要:

N-Alkyl-2,3,3-trimethyl-3H-indoleninium-5-sulfonates as the initial raw material,the water-soluble asymmetrical squarylium indocyanine dyes were synthesized by two-step synthesis method and solid-phase synthesis method,respectively.In two-step synthesis method,a series of squarylium hemicyanine dyes were synthesized by condensation of squaric acid with various N-alkyl-2,3,3-trimethyl-3H-indoleninium-5-sulfonates,then the water-soluble asymmetrical squarylium indocyanine dyes were synthesized by condensation of squarylium hemicyanine dyes with another N-alkyl-2,3,3-trimethyl-3H-indoleninium-5-sulfonate.Solid-phase synthesis method mainly includes three steps.Firstly,squaric acid was linked to the solid-phase polymer support PEG with chemical bond using p-aminobenzoic acid as bridge.And then,squarylium hemicyanine dyes with solid-phase polymer support were synthesized by reaction of squaric acid linked solid-phase polymer support and N-alkyl-2,3,3-trimethyl-3H-indoleninium-5-sulfonates.Lastly,the water-soluble asymmetrical squarylium indocyanine dyes were gotten by condensation of squarylium hemicyanine dyes linked solid-phase polymer support with different indoleniniums and cuting off the solid-phase support from squarylium hemicyanine dyes.These raw dyes were purified by C-18 reverse phase column chromatograph.Their structures were confirmed by 1H NMR and MS.The spectral properties of the title products were checked.In the process of synthesizing of water-soluble asymmetrical squarylium indocyanine,it is found that the yields of the title products by solid-phase synthesis method are 2 times of those of traditional two-step method.Solid-phase synthesis method is more suitable to synthesize water-soluble asymmetrial squarylium indocyanine dyes.

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期刊信息
  • 《化学学报》
  • 北大核心期刊(2014版)
  • 主管单位:中国科学院
  • 主办单位:中国化学会 中国科学院上海有机化学研究所
  • 主编:周其林
  • 地址:上海市零陵路345号
  • 邮编:200032
  • 邮箱:hxxb@sioc.ac.cn
  • 电话:021-54925085
  • 国际标准刊号:ISSN:0567-7351
  • 国内统一刊号:ISSN:31-1320/O6
  • 邮发代号:4-209
  • 获奖情况:
  • 首届国家期刊奖,第二届国家期刊奖提名奖,中国期刊方阵“双高期刊”
  • 国内外数据库收录:
  • 俄罗斯文摘杂志,美国化学文摘(网络版),荷兰文摘与引文数据库,美国科学引文索引(扩展库),日本日本科学技术振兴机构数据库,中国中国科技核心期刊,中国北大核心期刊(2004版),中国北大核心期刊(2008版),中国北大核心期刊(2011版),中国北大核心期刊(2014版),英国英国皇家化学学会文摘,中国北大核心期刊(2000版)
  • 被引量:28694