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
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1,2∗
(1. 江苏第二师范学院 生命科学与化学化工学院,南京 210013; 2. 南京医科大学 生物医学工程与信息学院,南京 210029)
Synthesis, Crystal Structure and Theoretical Calculation of a Pressure-sensitive Dye Based on Phthalide
Huang Yinke 1 Wang Yinyuan 1 Li Jiarui 1 Chen Lulu 1 Gong Ziyue 1 Jiang Dawei 1 Huang Bin 1,2∗
(1. College of Life Sciences, Chemistry and Chemical Engineering, Jiangsu Second Normal University, Nanjing 210013, China; 2. School of Biomedical Engineering and Informatics, Nanjing Medical University, Nanjing 210029, China)
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。
关键词：压敏染料 合成 苯酞 缩合 氧化 单晶分析；
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 ultravioletvisible 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.
Keywords：pressure-sensitive dye; synthesis; phthalide; condensation; oxidation; single crystal analysis;