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

doi:10.6023/cjoc201712009

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

Articles

具有聚集诱导发光现象效应的异长叶烷酮基锌离子荧光探针及其在植物细胞成像中的应用

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

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,E-mail:wangshifa65@163.com E-mail:wangshifa65@163.com
基金资助:
南京林业大学博士研究生基金会、国家自然科学基金（No.31470592）、江苏省高校自然科学研究重大项目（No.14KJ220001）、油性树脂的绿色加工及高效利用的关键技术（No.2016YFD0600804）资助项目.

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

Wang Zhonglong^a, Yang Jinlai^b, Yang Yiqin^c, Xu Xu^a,e, Li Mingxin^a, Zhang Yan^a, Fang Hua^b, Xu Haijun^a,e, Wang Shifa^a,e

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 E-mail:wangshifa65@163.com
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).

1. Aggregation-Induced Emission-Active Fluorescent Probe for Zn²⁺ Based on Isolongifolanone and Its Application in Plant-Cell Imaging.PDF(2380KB)

Abstract

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

Cite this article

Wang Zhonglong, Yang Jinlai, Yang Yiqin, Xu Xu, Li Mingxin, Zhang Yan, Fang Hua, Xu Haijun, Wang Shifa. Aggregation-Induced Emission-Active Fluorescent Probe for Zn²⁺ Based on Isolongifolanone and Its Application in Plant-Cell Imaging[J]. Chin. J. Org. Chem., 2018, 38(6): 1401-1413.

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具有聚集诱导发光现象效应的异长叶烷酮基锌离子荧光探针及其在植物细胞成像中的应用

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

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