酚酞衍生物的合成及其变色反应

引用本文: 申杨, 朱涵熙, 程立言, 庄俊鹏, 王涛. 酚酞衍生物的合成及其变色反应[J]. 大学化学, 2023, 38(5): 202-210. doi: 10.3866/PKU.DXHX202207097 shu

Citation: Yang Shen, Hanxi Zhu, Liyan Cheng, Junpeng Zhuang, Tao Wang. Synthesis of Phenolphthalein Derivatives and Their Color Change Reaction[J]. University Chemistry, 2023, 38(5): 202-210. doi: 10.3866/PKU.DXHX202207097 shu

酚酞衍生物的合成及其变色反应

申杨 ^1, ,
朱涵熙 ^1, ,
程立言 ^2, ,
庄俊鹏 ^2, ,
王涛 ^2,

1.
北京化工大学材料科学与工程学院, 北京 100029;
2.
北京化工大学化学学院, 北京 100029
基金项目:
北京化工大学本科教改项目(2018BHDJGZ02,2021BHDJGYB25)

摘要: 为了提高化学及相关专业高年级本科生有机化学实验的综合技能，本文设计了酚酞衍生物的合成、分离、紫外光谱的测定以及趣味变色的综合实验。分别通过四种苯酚的衍生物，在甲基磺酸中与邻苯二甲酸酐反应合成了酚酞衍生物，通过中和、萃取、抽滤、旋蒸、重结晶等基本有机合成的操作分离提纯。酚酞衍生物的乙醇溶液均是无色的，但随着取代基的变化，酚酞衍生物的碱性水溶液的颜色从红色向蓝色逐渐过渡。这一现象清楚地表明了取代基的给电子效应使得酚酞碱式结构的紫外最大吸收波长发生了明显的红移。酚酞衍生物在pH < 0的强酸溶液中显色，而在pH > 12的强碱性水溶液中是无色的，这与酚酞在不同pH下的分子结构密切相关。本实验用Gaussian软件优化了不同pH条件下酚酞衍生物的结构，探讨了酚酞衍生物的分子结构和颜色之间的关系。最后利用酚酞的酸碱变色反应，设计了多组趣味实验，让学生深刻体会化学实验中的学以致用和寓教于乐。

关键词:

English

Synthesis of Phenolphthalein Derivatives and Their Color Change Reaction

1.
College of Materials Science and Engineering, Beijing University of Chemical Technology, Beijing 100029, China;
2.
College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China
Received Date: 21 July 2022

Abstract: To improve the fundamental and essential experimental skills in organic chemistry for senior undergraduates majoring in chemistry and related disciplines, a comprehensive experimental procedure, including the synthesis, separation, UV-Vis spectrum analysis, and color change observation of phenolphthalein derivatives, was designed. The phenolphthalein derivatives were synthesized using four different phenol derivatives with phthalic anhydride in methane sulfonic acid, and separated and purified by standard organic synthesis operations, such as neutralization, extraction, suction filtration, rotary evaporation, and recrystallization. The ethanolic solutions of the phenolphthalein derivatives were colorless; however, the color of the alkaline aqueous solution of the phenolphthalein derivatives gradually transitioned from red to blue with the change of substituents. This phenomenon shows that the electron-donating effect of the substituents causes a redshift of the maximum absorption wavelength of these phenolphthalein derivatives in alkaline aqueous solution. Phenolphthalein derivatives are red to blue in strong acid solution with pH < 0, but colorless in strong alkaline aqueous solution with pH > 12, which is closely related to their molecular structure in different pH solutions. In this experiment, Gaussian software was used to optimize the phenolphthalein molecules under different pH conditions, and the relationship between the molecular structure of the phenolphthalein derivatives and their colors was discussed. Finally, based on the acid-base color-change reaction of phenolphthalein, other interesting experiments were designed to enable students to deeply understand how to apply new knowledge and enjoy learning through practical chemistry experiments.

Key words:

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1.
沈阳化工大学材料科学与工程学院沈阳 110142

酚酞衍生物的合成及其变色反应

English

Synthesis of Phenolphthalein Derivatives and Their Color Change Reaction

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酚酞衍生物的合成及其变色反应

English

Synthesis of Phenolphthalein Derivatives and Their Color Change Reaction

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

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