大学化学 >> 2023, Vol. 38 >> Issue (5): 227-233.doi: 10.3866/PKU.DXHX202207148

化学实验 上一篇    下一篇

深蓝色荧光苯并呋喃并吲哚的绿色合成

虞喜翔, 叶栩彤, 邓睿, 龚跃法, 钟芳锐()   

  • 收稿日期:2022-07-30 录用日期:2022-09-22 发布日期:2022-10-10
  • 通讯作者: 钟芳锐 E-mail:chemzfr@hust.edu.cn

Green Synthesis of Deep Blue Fluorescent Benzofuroindole

Xixiang Yu, Xutong Ye, Rui Deng, Yuefa Gong, Fangrui Zhong()   

  • Received:2022-07-30 Accepted:2022-09-22 Published:2022-10-10
  • Contact: Fangrui Zhong E-mail:chemzfr@hust.edu.cn

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摘要：

将酚与吲哚的催化有氧氧化[3+2]环化反应绿色构建深蓝色荧光苯并呋喃并吲哚的科研成果转化为本科教学实验，涉及路易斯酸催化、亲电取代反应、共轭加成等有机化学基础理论，包含薄层色谱、柱层析纯化、紫外-可见吸收/荧光光谱测定、核磁共振波谱分析等实验技能，融入安全、可持续化学理念等课程思政元素，综合训练学生的科学思维、探究思维和解决复杂合成问题的综合能力。

关键词: 苯并呋喃并吲哚, 有氧氧化, [3+2]环加成, 荧光材料

Abstract:

We present a new undergraduate teaching experiment inspired by recent scientific advances toward the sustainable synthesis of deep blue fluorescent benzofuroindoles via the catalytic aerobic oxidation [3+2] cyclization of phenol and indole. The experiment teaches basic theoretical knowledge of organic chemistry, such as Lewis acid catalysis, electrophilic substitution, conjugate addition, and practical skills, including thin layer chromatography, column chromatography purification, UV-Vis absorption/fluorescence spectroscopy, and nuclear magnetic resonance spectroscopy. It integrates the ideological elements of green chemistry, environmental protection, safety, and sustainable chemistry, among others, and provides comprehensive training in scientific thinking, scientific inquiry, and complex problem solving in synthetic chemistry.

Key words: Benzofuroindole, Aerobic oxidation, [3+2] cyclization, Fluorescence material