Tetrahedron ( IF 2.1 ) Pub Date : 2019-02-11 , DOI: 10.1016/j.tet.2019.02.023 Hongliang Liu , Hailong Wang , Gang Liu , Shouzhi Pu , Haiquan Zhang
A pyrimidine-substituted perylene diimide (Pyrimidine-PDI), in which the electron-deficient N-heterocyclic pyrimidine rings were introduced into the core positions, were synthesized to produce a conductometric film device for the sensitive detection of hydrazine (NH2NH2) vapor at room temperature under ambient conditions. The Pyrimidine-PDI film device exhibited ultrafast response, excellent reproducibility, excellent selectivity and good long-term stability towards hydrazine vapor. The response and recovery time of the device was calculated to be very low as 0.4 s and 0.6 s for hydrazine vapor at sub-ppm level (0.1 ppm). Moreover, the effect of the film thickness, relative humidity and temperature on the sensing performance were also studied. To understand the sensing mechanism, the core-benzene group perylene diimide (Ph-PDI) was also designed as a comparison. The film devices of Pyrimidine-PDI and Ph-PDI to hydrazine vapor were investigated with UV–vis spectra and cyclic voltammetry, which indicated that the redox of PDIs played a critical role in the sensing process. The electrochemical properties also indicated that electron-deficient N-heterocyclic pyrimidine rings could effectively lower the LUMO energy level and improve the response of the device.
中文翻译:
使用嘧啶取代的per二酰亚胺薄膜器件对亚ppm级的肼蒸气进行超灵敏感测
合成了嘧啶取代的per二酰亚胺(Pyrimidine-PDI),其中将缺电子的N-杂环嘧啶环引入到核心位置,从而制得用于灵敏检测肼(NH 2 NH 2)的电导膜装置)在室温下于环境条件下蒸发。嘧啶-PDI薄膜器件表现出超快的响应速度,出色的重现性,出色的选择性以及对肼蒸汽的长期稳定性。计算得出,对于低于ppm级(0.1 ppm)的肼蒸汽,该器件的响应和恢复时间非常短,仅为0.4 s和0.6 s。此外,还研究了膜厚度,相对湿度和温度对传感性能的影响。为了理解传感机理,还设计了芯苯基per二酰亚胺(Ph-PDI)作为比较。用紫外可见光谱和循环伏安法研究了嘧啶-PDI和Ph-PDI制备肼蒸汽的薄膜装置,这表明PDI的氧化还原在传感过程中起着至关重要的作用。N-杂环嘧啶环可有效降低LUMO能级并改善器件的响应。