新型二吡咯骨架双腙受体的合成及识别性能研究
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摘要
实验设计合成一种含有二吡咯甲烷骨架的"钳形"阴离子受体,利用紫外可见光谱滴定实验研究受体化合物分别在纯乙腈体系和含水5%的乙腈体系中与八种常见阴离子的识别作用。实验结果表明:该受体化合物在纯乙腈体系中对Ac O~-、F`-、HSO_4~-、H_2PO_4~-有较好的识别作用,结合常数Ka均大于10~3,而在含水5%的乙腈体系中只对Ac O~-和F~-有识别作用,且对F~-的结合力远大于对Ac O~-的结合力。由此可见,二吡咯甲烷骨架的"诱导契合"效应对阴离子识别具有独特优势。
A anion receptor bearing bishydrazone and two pyrrole skeleton was designed and synthesized. The binding properties of the receptor with anions were investigated by UV-vis. Results show that the anion receptor possesses excellent recognition capability for AcO~-,F~-,HSO_4~- and H_2 PO_4~- in the pure acetonitrile system. Binding constant Ka was greater than 10~3,and the while only AcO~- and F~- can be recognized in the acetonitrile system with 5% water. This work shows that the "induced fit"effect of dipyrroomethane skeleton has a unique advantage in anionic recognition.
A anion receptor bearing bishydrazone and two pyrrole skeleton was designed and synthesized. The binding properties of the receptor with anions were investigated by UV-vis. Results show that the anion receptor possesses excellent recognition capability for AcO~-,F~-,HSO_4~- and H_2 PO_4~- in the pure acetonitrile system. Binding constant Ka was greater than 10~3,and the while only AcO~- and F~- can be recognized in the acetonitrile system with 5% water. This work shows that the "induced fit"effect of dipyrroomethane skeleton has a unique advantage in anionic recognition.
引文
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[3]刘阁，刘艳红．基于苯腙类衍生物的阴离子光学传感器的研究[J]．化学研究与应用，2014,24(6):872-876.
[4]徐维霞，马占营，范广，等．缩氨基硫脲受体的合成及阴离子识别规律研究[J]．化学研究与应用，2009,21(7):989-993.
[5]赵志刚，刘兴利，李清寒，等．分子钳人工主体研究进展[J]．有机化学，2009,29(9):1336-1353.
[6]韩文强，田茂忠，冯锋，等．双臂罗丹明类荧光探针应用于Hg2+的识别[J]．理化检验-化学分册，2018,54(3):255-259.
[7]范晓丽，吕磊红，张蔚，等．荧光光谱法测定氧氟沙星的含量[J]．理化检验-化学分册，2016,52(3):288-291.
[8]KNINGT A S,KULKARNI R U,ZHOU E Y,et al. A moduar platform to peptoid-based selective fluorescent metal develop sensors[J]. Chemical Communications,2017,53(24):3477-3480.
[9]RIVADEHI S,REID E F,HOGAN C F,et al. Fluoride-selective optical sensor based on the dipyrrolyl-tetrathiafulvalene chromophore[J]. 2012,10(4):705"709.
[10]张有明，秦霄萍，林奇，等．基于酰腙和酚羟基的阴离子受体的合成及其在含水介质中的阴离子比色识别性能[J]．有机化学，2010,30(4):534"538.
[11]PANDIAN T S,CHO S J,KANG J. Dihydrogen Phosphate as a Hydrogen-Bonding Donor Element:Anion Receptors Based on Acylhydrazone[J]. J Org Chem,2013,78(23):12121"12127.
[12]ZHOU Y H,ZHENG P C,BAO X P. Selective recognition and discrimination of H2PO4-and F-based on a cleft-shaped anion receptor incorporating bisamide and bispyrrole groups[J]. Supramolecular Chemistry,2014,26(10):761-768.
[13]周玉惠，罗仕辉，鲍小平．基于二吡咯甲烷的双腙类阴离子受体性质研究[J]．化学研究应用，2015,27(7):979-983.
[14]ZHANG F,ZHOU Y H,BAO X P. Synthesis and anion binding properties of 1,8-disulfonamidocarbazole dipyrromethane Schiffbase macrocycle&its amine analogue[J]. Supramolecular Chemistry,2016,28(3):305-313.
[15]SHAO J,LIN H,YU M,et a1. Study on acetate ion recognition and sensing in aqueous media using a novel and simple colorimetric sensor and its analytical application[J]. Talanta,2008,75(2):551-555.
[16]BOIOCCHI M,BOCA L D,GMEZ D E,et al. Nature of UreaFluoride Interaction:Incipient and Definitive Proton Transfer[J].J Am Chem Soc,2004,126(50):16507-16514.