Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (6): 1401-1413.DOI: 10.6023/cjoc201712009 Previous Articles     Next Articles

Special Issue: 荧光探针-生物传感合辑 有机超分子化学合辑



王忠龙a, 杨金来b, 杨益琴c, 徐徐a,e, 李明新a, 张燕a, 方华b, 徐海军a,e, 王石发a,e   

  1. a 南京林业大学化学工程学院 南京 210037;
    b 国家林业局竹子研究开发中心 浙江省竹子高效加工重点实验室 杭州 310012;
    c 南京林业大学轻工科学与工程学院 南京 210037;
    d 南京林业大学理学院 南京 210037;
    e 南京林业大学林业资源高效加工利用协同创新中心 南京 210037
  • 收稿日期:2017-12-05 修回日期:2018-03-05 发布日期:2018-03-16
  • 通讯作者: 王石发,
  • 基金资助:


Aggregation-Induced Emission-Active Fluorescent Probe for Zn2+ Based on Isolongifolanone and Its Application in Plant-Cell Imaging

Wang Zhonglonga, Yang Jinlaib, Yang Yiqinc, Xu Xua,e, Li Mingxina, Zhang Yana, Fang Huab, Xu Haijuna,e, Wang Shifaa,e   

  1. a College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
    b Key Laboratory of High Efficient Processing of Bamboo of Zhejiang Province, China National Bamboo Research Center, Hangzhou 310012;
    c Institute of Light Industry Science and Engineering, Nanjing Forestry University, Nanjing 210037;
    d Department of Chemistry and Material Science, College of Science, Nanjing Forestry University, Nanjing 210037;
    e Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037
  • Received:2017-12-05 Revised:2018-03-05 Published:2018-03-16
  • Contact: 10.6023/cjoc201712009
  • Supported by:

    Project supported by the Doctorate Fellowship Foundation of Nanjing Forestry University, the National Natural Science Foundation of China (No. 31470592), the University Science Research Project of Jiangsu Province (No. 14KJ220001), the Key Technology of Green Processing and Efficient Utilization on Oleoresin (No. 2016YFD0600804).

A series of hexahydroquinazolin-2-amine-based derivatives have been designed and synthesized from renewable isolongifolanone. Their solid states exhibited an enhanced emission and a dark green to bright yellow color range. In addition to good thermal stability, their solid-state fluorescence is not readily restricted by multiple conventional factors such as long term UV irradiation, increasing operated pressure and elevated heating temperature. In contrast to the derivatives which undergo serious aggregation-caused quenching (ACQ), the dimethylamino-substituted derivative 1-6,6,10,10-tetramethyl-4-(4'-(N,N-dimethylamino)phenyl)-5,7,8,9,10,10a-hexahydro-6H-6a,9-methanobenzo[h]quinazolin-2-imino)methyl)naphthalen-2-ol (3e) demonstrate obvious aggregation-induced emission (AIE) characteristics. Moreover, these fluorescent derivatives were also used for specific and sensitive sensing of Zn2+ ion in aqueous solutions. Then, their photophysical mechanisms were obtained by the density functional theory calculations. These probes were successfully applied to image Zn2+ ion in pollen grains of Althaea rosea.

Key words: isolongifolanone, aggregation-induced emission, aggregation-caused quenching, Zn2+ ion, fluorescence imaging