Abstract In this study, the three novel fluoro substituted asymmetric zinc phthalocyanines substituted with 3-hydroxy-3-methyl-1-butynyl (3), ethynyl (4), and 4-nitrophenylethynyl (5) groups were synthesized and characterized by Fourier-transform infrared spectrophotometer, ultraviolet–visible, proton nuclear magnetic resonance, and matrix-assisted laser desorption/ionization time-of-flight mass spectroscopy. The thickness dependence of relative humidity sensing performance of these compounds using quartz crystal microbalance transducers in a broad operating range of humidity was investigated. Results from this preliminary analysis indicated that responses and the response and recovery times of the 3–5 compound-based relative humidity sensors strongly depended on the thickness of the sensory layer. Experimental studies indicated that the optimized thickness as 450 nm produces a good sensitivity, and the best response and recovery times. The relative humidity sensing results demonstrated that the quartz crystal microbalance sensor coated with peripherally substituted unsymmetrical zinc(II) phthalocyanines bearing nitrophenyl group was the most useful coating for the relative humidity sensing.

中文翻译：

---

一系列含氟和炔基的不对称锌 (II) 酞菁：使用基于 QCM 的传感器合成和检测湿度传感性能

摘要 本研究合成了三种被 3-羟基-3-甲基-1-丁炔基 (3)、乙炔基 (4) 和 4-硝基苯基乙炔基 (5) 取代的新型氟取代不对称锌酞菁，并通过傅里叶-变换红外分光光度计、紫外-可见光、质子核磁共振和基质辅助激光解吸/电离飞行时间质谱。使用石英晶体微天平换能器在较宽的湿度工作范围内研究了这些化合物的相对湿度传感性能的厚度依赖性。初步分析的结果表明，基于 3-5 种化合物的相对湿度传感器的响应以及响应和恢复时间在很大程度上取决于传感层的厚度。实验研究表明，优化的厚度为 450 nm 产生了良好的灵敏度，以及最佳的响应和恢复时间。相对湿度传感结果表明，涂​​覆有外围取代的带有硝基苯基的不对称锌（II）酞菁的石英晶体微天平传感器是最适用于相对湿度传感的涂层。