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
收稿日期: 2017-12-05
修回日期: 2018-03-05
网络出版日期: 2018-03-16
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
Received date: 2017-12-05
Revised date: 2018-03-05
Online published: 2018-03-16
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).
以可再生的异长叶烷酮为原料，设计合成了五种六氢喹唑啉-2-胺基衍生物.化合物在固体状态时呈现出增强的荧光强度以及从暗绿色到亮黄色的荧光颜色的转变.除了良好的热稳定性之外，化合物的固态荧光不容易受到多种常见因素的干扰，比如长时间的紫外照射、增强的制片压力以及升高的加热温度.与遭受严重不利的聚集荧光猝灭效应（ACQ）的化合物相反，二甲氨基取代基构建的1-（（（6，6，10，10-四甲基-4-（4'-（二甲基氨基）苯基）-5，7，8，9，10，10a-六氢-6H-6a，9-桥亚甲基苯并[h]-2-喹啉基）亚胺基）甲基）萘-2-酚（3e）呈现出明显的聚集诱导发光现象（AIE）.而且，荧光化合物在水溶液中还可以用于对锌离子的专一和灵敏的检测.而后，采用密度泛函理论计算对化合物的光物理性质进行研究.荧光探针还被成功的应用于蜀葵的花粉粒内的锌离子成像.
王忠龙 , 杨金来 , 杨益琴 , 徐徐 , 李明新 , 张燕 , 方华 , 徐海军 , 王石发 . 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[J]. 有机化学, 2018 , 38(6) : 1401 -1413 . DOI: 10.6023/cjoc201712009
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.
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