大学化学 >> 2020, Vol. 35 >> Issue (12): 227-232.doi: 10.3866/PKU.DXHX201911053

化学实验 上一篇    下一篇

诺贝尔化学奖类大学生创新实验——Suzuki偶联反应制备DPP类荧光染料

熊就凯1, 赵美娟1, 王亚男1, 边刚1,*(), 戎瑞雪2,*(), 王克让1,*()   

  1. 1 河北大学化学与环境科学学院, 药物化学与分子诊断教育部重点实验室, 河北 保定 071002
    2 河北大学基础医学院, 河北 保定 071000
  • 收稿日期:2019-11-25 录用日期:2020-02-19 发布日期:2020-02-27
  • 通讯作者: 边刚,戎瑞雪,王克让 E-mail:13513408758@126.com;rongruixue_1234@163.com;kerangwang@163.com
  • 作者简介:王克让, Email: kerangwang@163.com
    戎瑞雪,Email:rongruixue_1234@163.com
    边刚, Email: 13513408758@126.com
  • 基金资助:
    河北省教改项目(2016GJJG014);河北省研究生示范课程项目(KCJSX2018009);河北大学大学生创新创业训练项目(2017141);河北大学化学与环境科学学院教改项目(HBUHXJG2016-03)

Innovative Experiment for Students Based on Nobel Prizes in Chemistry: Construction of Fluorescent DPP Derivative by Suzuki Reaction

Jiukai Xiong1, Meijuan Zhao1, Yanan Wang1, Gang Bian1,*(), Ruixue Rong2,*(), Kerang Wang1,*()   

  1. 1 Key Laboratory of Medicinal Chemistry and Molecular Diagnosis(Ministry of Education), College of Chemistry and Environmental Science, Hebei University, Baoding 071002, Hebei Province, P. R. China
    2 Department of Immunology, School of Basic Medical Science, Hebei University, Baoding 071000, Hebei Province, P. R. China
  • Received:2019-11-25 Accepted:2020-02-19 Published:2020-02-27
  • Contact: Gang Bian,Ruixue Rong,Kerang Wang E-mail:13513408758@126.com;rongruixue_1234@163.com;kerangwang@163.com

摘要:

以丁二酸二异丙酯和对溴苯甲腈为原料,经闭环和偶联反应合成了吡咯并吡咯二酮(DPP)类分子,与1-溴-2-甲基丁烷经亲核取代反应,进而经Suzuki偶联反应与9-蒽硼酸反应制备了DPP类染料分子。化合物结构经1H NMR、13C NMR和HRMS等表征,并且DPP类染料分子具有强的荧光特征,在氯仿溶液和固态下的荧光量子效率可分别达88.4%和78.9%。

关键词: 诺贝尔化学奖, Suzuki偶联反应, 吡咯并吡咯二酮, 荧光

Abstract:

Fluorescent diketopyrrolopyrrole (DPP) derivative was synthesized by coupling reaction, nucleophilic substitution reaction and Suzuki reaction, which was fully characterized by NMR spectroscopy and HRMS. Furthermore, the DPP derivative showed high fluorescence quantum yields of 88.4% and 78.9% in solvent and solid states.

Key words: Nobel Prizes in chemistry, Suzuki coupling reaction, Diketopyrrolopyrrole, Fluorescence

MSC2000: 

  • G64