Citation: Shuixing Dai,  Jilei Jiang,  Yuxiao Wang,  Jinqi Hu,  Minghua Huang. Application of Knoevenagel Reaction in Organic Chemistry Teaching[J]. University Chemistry, ;2025, 40(5): 334-341. doi: 10.12461/PKU.DXHX202405208 shu

Application of Knoevenagel Reaction in Organic Chemistry Teaching

  • Corresponding author: Minghua Huang, huangminghua@ouc.edu.cn
  • Received Date: 31 May 2024
    Revised Date: 19 August 2024

  • This study integrates fundamental organic chemistry concepts, including the Knoevenagel condensation reaction, with cutting-edge research in organic solar cells. Through a laboratory experiment, students synthesized a wide-bandgap fused-ring electron acceptor material, A831. Analysis of the experimental data demonstrated that diminishing the electron-withdrawing ability of the terminal groups elevated the material’s lowest unoccupied molecular orbital (LUMO) energy level, thereby enhancing the voltage output of the organic solar cells. This experiment cultivates students’ ability to apply foundational knowledge to solve research problems, embodying the educational philosophy of “fundamental knowledge – practical application”. It is particularly suitable as a comprehensive course for senior undergraduate students.
  • 加载中
    1. [1]

      Jones, G. Org. React. 1967, 15, 204.

    2. [2]

      Xiao, B.; Tang, A.; Zhang, J.; Mahmood, A.; Wei, Z.; Zhou, E. Adv. Energy Mater. 2017, 7, 1602269.

    3. [3]

      Xiao, B.; Tang, A.; Yang, J.; Wei, Z.; Zhou, E. ACS Macro Lett. 2017, 6, 410.

    4. [4]

      Dai, T.; Tang, A.; Meng, Y.; Dong, C.; Cong, P.; Lu, J.; Du, J.; Zhong, Y.; Zhou, E. Angew. Chem. Int. Ed. 2024, 63, e202403051.

    5. [5]

      Ma, Y.; Sun, R.; Chen, Z.; Zhang, S.; Cai, D.; Wan, S.; Lin, W.; Zhang, S.; Tu, Q.; Ma, W.; et al. Nano Energy 2023, 107, 108116.

    6. [6]

      Ma, Y.; Zhang, M.; Wan, S.; Yin, P.; Wang. P.; Cai, D.; Liu, F.; Zheng, Q. Joule 2021, 5, 197.

    7. [7]

      Demeter, D.; Rousseau, T.; Leriche, P.; Cauchy, T.; Po, R.; Roncali, J. Adv. Funct. Mater. 2011, 21, 4379.

    8. [8]

      Ye, L.; Xie, Y.; Xiao, Y.; Song, J.; Li, C.; Weng, K.; Lu, X.; Tan, S.; Yan, M. J. Mater. Chem. A 2019, 7, 8055.

    9. [9]

      Zhu, Y.; Guo, H.; Xiong, X.; Cai, D.; Ma, Y.; Zheng, Q. Adv. Mater. 2024, 36, 2314169.

    10. [10]

      Dai, S.; Zhan, X. Acta Polym. Sin. 2017, 11, 1706.

    11. [11]

      Dai, S.; Zhao, F.; Zhang, Q.; Lau, T. K.; Li, T.; Liu, K.; Ling, Q.; Wang, C.; Lu, X.; You, W.; et al. J. Am. Chem. Soc. 2017, 139 (3), 1336.

    12. [12]

      Dai, S.; Li, T.; Wang, W.; Xiao, Y.; Lau, T. K.; Li, Z.; Liu, K.; Lu, X.; Zhan, X. Adv. Mater. 2018, 30 (15), 1706571.

    13. [13]

      Zhao, F.; Dai, S.; Wu, Y.; Zhang, Q.; Wang, J.; Jiang, L.; Ling, Q.; Wei, Z.; Ma, W.; You, W.; et al. Adv. Mater. 2017, 29 (18), 1700144.

    14. [14]

      Dai, S.; Zhou, J.; Chandrabose, S.; Shi, Y.; Han, G.; Chen, K.; Xin, J.; Liu, K.; Chen, Z.; Xie, Z.; et al. Adv. Mater. 2020, 32 (21), 2000645.

    15. [15]

      Dai, S.; Zhou, J.; Lau, T.-K.; Rech, J. J.; Liu, K.; Xue, P.; Xie, Z.; Lu, X.; You, W.; Zhan, X. Small Struct. 2020, 1 (2), 2000006.

    16. [16]

      Dai, S.; Xiao, Y.; Xue, P.; James Rech, J.; Liu, K.; Li, Z.; Lu, X.; You, W.; Zhan, X. Chem. Mater. 2018, 30 (15), 5390.

    17. [17]

      Jia, B.; Dai, S.; Ke, Z.; Yan, C.; Ma, W.; Zhan, X. Chem. Mater. 2017, 30 (1), 239.

    18. [18]

      Xue, P.; Dai, S.; Lau, T.-K.; Yu, J.; Zhou, J.; Xiao, Y.; Meng, K.; Xie, Z.; Lu, G.; Lu, X.; et al. Solar RRL 2020, 4 (7), 2000115.

    19. [19]

    20. [20]

      Zhang, M.; Guo, X.; Zhang, S.; Hou, J. Adv. Mater. 2014, 26 (7), 1118.

  • 加载中
    1. [1]

      Yawen GuoDawei LiYang GaoCuihong Li . Recent Progress on Stability of Organic Solar Cells Based on Non-Fullerene Acceptors. Acta Physico-Chimica Sinica, 2024, 40(6): 2306050-0. doi: 10.3866/PKU.WHXB202306050

    2. [2]

      Guowen Xing Guangjian Liu Le Chang . Five Types of Reactions of Carbonyl Oxonium Intermediates in University Organic Chemistry Teaching. University Chemistry, 2025, 40(4): 282-290. doi: 10.12461/PKU.DXHX202407058

    3. [3]

      Zhenxing Liu Jiaen Hu Zishi Cheng Xinqi Hao . 基础有机化学教学中烯烃的氧化反应. University Chemistry, 2025, 40(6): 139-144. doi: 10.12461/PKU.DXHX202408107

    4. [4]

      Yikai WangXiaolin JiangHaoming SongNan WeiYifan WangXinjun XuCuihong LiHao LuYahui LiuZhishan Bo . Thickness-Insensitive, Cyano-Modified Perylene Diimide Derivative as a Cathode Interlayer Material for High-Efficiency Organic Solar Cells. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-0. doi: 10.3866/PKU.WHXB202406007

    5. [5]

      Aiyi Xin Jiawei Li Xinyang Ran Chuanjiang Fu Zhiguo Wang . Collaborative Science and Education Based Experimental Design in Organic Chemistry: A Case Study of the Nucleophilic Substitution Reaction of 2-Hydroxymethyl-4,6-Di-Tert-Butylphenol. University Chemistry, 2025, 40(5): 366-375. doi: 10.12461/PKU.DXHX202407031

    6. [6]

      Daojuan Cheng Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105

    7. [7]

      Fuxian Wan Ying Li Yuanhong Zhang Shuhua Zhu Jing Xu Yanfang Wang Lili Zhang . Exploration and Practice of Teaching in Agricultural Characteristic Organic Chemistry Course. University Chemistry, 2024, 39(2): 298-306. doi: 10.3866/PKU.DXHX202308041

    8. [8]

      Zhichang Xiao Xiaohui Li Ling Zhang Huimin Liu . Exploration of Ideological and Political Construction in University Foundation Course of Organic Chemistry. University Chemistry, 2024, 39(2): 314-320. doi: 10.3866/PKU.DXHX202308058

    9. [9]

      Linlin Wang Yanqin Chen Feng Li Ruikang Tan . Practical Exploration of Graded Teaching in the Public Organic Chemistry Course for Agricultural Science Students. University Chemistry, 2025, 40(7): 48-54. doi: 10.12461/PKU.DXHX202409054

    10. [10]

      Fei Xie Shichong Yu Ting Wang Yongsheng Jin Dazhi Zhang Yumeng Hao . Practice and Exploration of O-PIRTAS Flipped Classroom in Organic Chemistry Course. University Chemistry, 2024, 39(4): 238-243. doi: 10.3866/PKU.DXHX202310055

    11. [11]

      Hui Liu Shupeng Zhang Yuntian Zhang Wei Dong Yuji Liu Bingxin Deng Dongping Chen Yongxing Tang . Research on the Application of Virtual Reality (VR) Technology in the Teaching of Organic Chemistry. University Chemistry, 2024, 39(8): 64-71. doi: 10.3866/PKU.DXHX202312028

    12. [12]

      Jian He Dinglin Zhang Liping Wu Ying Bao Xiaochao Yang . 知识网络构建策略在有机化学教学中的应用及效果分析. University Chemistry, 2025, 40(8): 66-71. doi: 10.12461/PKU.DXHX202410092

    13. [13]

      Dawei Zhang Yuqian Zhao Mingyu Jiao Yan Wang . Cultivation of Students’ Critical Thinking in the Practice of Ideological and Political in Organic Chemistry Courses: Taking the Discrimination and Analysis of Chemical Rumors as Examples. University Chemistry, 2025, 40(4): 181-188. doi: 10.12461/PKU.DXHX202405211

    14. [14]

      Yong Zhao Yunmei Bi Liqin Wang Rui Zhan Guoli Huang . Construction and Practice of Organic Chemistry Course in Normal Universities from the Perspective of First-Class Curriculum. University Chemistry, 2024, 39(8): 54-63. doi: 10.3866/PKU.DXHX202312088

    15. [15]

      Xipu He Wengui Duan Guishan Lin . Reform and Practice of Organic Chemistry Teaching for Non-Chemistry Major under the Four New Construction: Taking the Organic Chemistry Course Reform of Biological Science Major at Guangxi University as an Example. University Chemistry, 2025, 40(7): 42-47. doi: 10.12461/PKU.DXHX202408021

    16. [16]

      Benhua Wang Chaoyi Yao Yiming Li Qing Liu Minhuan Lan Guipeng Yu Yiming Luo Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070

    17. [17]

      Yong Wang Yingying Zhao Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009

    18. [18]

      Zhanhui Yang Jiaxi Xu . (m+n+…) or [m+n+…]cycloaddition?. University Chemistry, 2025, 40(3): 387-389. doi: 10.12461/PKU.DXHX202406032

    19. [19]

      Tongyan Yu Pan Xu . Visible-Light Photocatalyzed Radical Rearrangement Reaction. University Chemistry, 2025, 40(7): 169-176. doi: 10.12461/PKU.DXHX202409070

    20. [20]

      Ruonan LiShijie LiangYunhua XuCuifen ZhangZheng TangBaiqiao LiuWeiwei Li . Chlorine-Substituted Double-Cable Conjugated Polymers with Near-Infrared Absorption for Low Energy Loss Single-Component Organic Solar Cells. Acta Physico-Chimica Sinica, 2024, 40(8): 2307037-0. doi: 10.3866/PKU.WHXB202307037

Metrics
  • PDF Downloads(0)
  • Abstract views(691)
  • HTML views(92)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return