化工时刊2024,Vol.38Issue(1) :1-6.DOI:10.16597/j.cnki.issn.1002-154x.2024.01.001

一种苯酞类压敏染料的合成、晶体结构和理论计算

Synthesis,Crystal Structure and Theoretical Calculation of a Pressure-sensitive Dye Based on Phthalide

黄尹柯 王音原 李嘉睿 陈露露 龚子悦 姜大炜 黄斌
化工时刊2024,Vol.38Issue(1) :1-6.DOI:10.16597/j.cnki.issn.1002-154x.2024.01.001

一种苯酞类压敏染料的合成、晶体结构和理论计算

Synthesis,Crystal Structure and Theoretical Calculation of a Pressure-sensitive Dye Based on Phthalide

黄尹柯 1王音原 1李嘉睿 1陈露露 1龚子悦 1姜大炜 1黄斌2
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作者信息

  • 1. 江苏第二师范学院生命科学与化学化工学院,南京 210013
  • 2. 江苏第二师范学院生命科学与化学化工学院,南京 210013;南京医科大学生物医学工程与信息学院,南京 210029
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摘要

以对二甲氨基苯甲醛和间二甲氨基苯甲酸为原料,经过缩合、水解和氧化得到中间体6-二甲氨基-2-(4-二甲氨基苯酰)苯甲酸,其再与1-丁基-2-甲基吲哚发生缩合反应得到目标化合物3-(4-二氨基苯基)-3-(1-丁基-2-甲基-吲哚-3-基)-6-二甲氨基苯酞,4步反应总收率58%.目标化合物的结构经1HNMR和单晶测试确证.基于紫外-可见吸收光谱分析结果,结合理论计算,研究了该化合物的变色机理.结果表明,化合物在酸性条件下发生水解和消除反应,增加分子共轭,导致吸收光谱红移,是影响该化合物变色的关键因素.

Abstract

With p-dimethylamino-benzaldehyde and m-dimethylamino-benzoic acid as raw materials,the intermediate 6-dimethylamino-2-(4-dimethylamino-benzoyl)-benzoic acid was obtained.Then the target compound 3-(4-dimethylaminobenzyl)-3-(1-butyl-2-methyl-indol-3-yl)-6-dimethylaminophthalide was prepared by condensation reaction between the intermediate and 1-butyl-2-methylindole.The total yield of four steps is 58%.The structure of the target compound was confirmed by 1HNMR spectrum and single crystal test.Based on ultraviolet-visible absorption spectra analysis and theoretical calculations,the discoloration mechanism of the compound was studied.The results showed that the discoloration of the compound could be mainly attributed to the hydrolysis and elimination reactions under acidic condition,leading to the increase of molecular conjugation and the red shift of the absorption spectra.

关键词

压敏染料/合成/苯酞/缩合/氧化/单晶分析

Key words

pressure-sensitive dye/synthesis/phthalide/condensation/oxidation/single crystal analysis

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基金项目

江苏省高等学校自然科学研究面上项目(19KJB150006)

江苏省大学生创新创业训练计划(202214436034Y)

出版年

2024
化工时刊
东南大学

化工时刊

影响因子:0.333
ISSN:1002-154X
参考文献量17
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