许根瑞, 李伟强, 吴沁, 张周, 黄超. 微波辅助一锅串联高效合成多样性吖啶酯及其D-A-D型pH荧光探针的应用[J]. 云南大学学报(自然科学版), 2022, 44(6): 1249-1256. doi: 10.7540/j.ynu.20220004
引用本文: 许根瑞, 李伟强, 吴沁, 张周, 黄超. 微波辅助一锅串联高效合成多样性吖啶酯及其D-A-D型pH荧光探针的应用[J]. 云南大学学报(自然科学版), 2022, 44(6): 1249-1256. doi: 10.7540/j.ynu.20220004
XU Gen-rui, LI Wei-qiang, WU Qin, ZHANG Zhou, HUANG Chao. Microwave-assisted one-pot tandem efficient synthesis of diversified acridinium esters and application of D-A-D structure pH fluorescent probes[J]. Journal of Yunnan University: Natural Sciences Edition, 2022, 44(6): 1249-1256. DOI: 10.7540/j.ynu.20220004
Citation: XU Gen-rui, LI Wei-qiang, WU Qin, ZHANG Zhou, HUANG Chao. Microwave-assisted one-pot tandem efficient synthesis of diversified acridinium esters and application of D-A-D structure pH fluorescent probes[J]. Journal of Yunnan University: Natural Sciences Edition, 2022, 44(6): 1249-1256. DOI: 10.7540/j.ynu.20220004

微波辅助一锅串联高效合成多样性吖啶酯及其D-A-D型pH荧光探针的应用

Microwave-assisted one-pot tandem efficient synthesis of diversified acridinium esters and application of D-A-D structure pH fluorescent probes

  • 摘要: 建立了一种吖啶酯类化合物高效合成的新方法,并基于该方法设计、合成了含D-A-D型的吖啶酯分子,对其pH荧光探针性能进行了探索和研究. 以简单易得的靛红和芳基硼衍生物为原料,乙醇介质微波辅助下,一锅串联以71%~89%的产率合成12个吖啶酯类衍生物. 设计合成并评价了其中D-A-D型吖啶酯类化合物在不同pH值下的荧光响应情况,提出可能的机理. 该合成方法具有原料简单易得,反应简洁高效等特点,基于D-A-D设计的吖啶酯探针在pH 1.94~4.06有灵敏的响应.

     

    Abstract: A new method for the efficient synthesis of acridine ester compounds was established, and based on this method, acridine ester molecules containing D-A-D structure were designed and synthesized, and the properties of pH fluorescent probes were explored and studied. Simply and easily obtained isatin and arylboron derivatives were used as raw materials, via ethanol-medium microwave assisted, one-pot tandem reaction to synthesized 12 acridine ester derivatives with a yield of 71%~89%. The D-A-D structure of acridine was designed and synthesized. The fluorescence response of ester compounds at different pH values was evaluated, and the possible mechanism was proposed. The reaction conditions are mild, meanwhile the raw materials are simple and easy to obtain, the operation is simple. The acridinium ester probe compound designed based on D-A-D has a sensitive response at pH 1.94−4.06.

     

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