Octa-substituted metallophthalocyanines [M = Ni(II), Zn(II), Co(II), and Cu(II)] carrying 3,4-dialkoxyphenyl tosylamino groups at the peripheral positions have been synthesized from 1,2-dicyano-4,5-bis[(3,4-dialkoxyphenyl-tosylamino)methyl]benzene in the presence of the corresponding anhydrous metal salt. Next to the metal ion center, the length of the alkyl chains in the dialkoxyphenyl moiety (n = 4, 5, 6, and 12) was varied. In total, sixteen soluble phthalocyanines have been characterized by elemental analysis, FT-IR and 1H-NMR spectroscopy as well as mass spectrometry. Furthermore, the gas sensing properties of these new compounds have been studied using quartz crystal microbalance transducers. The sensing properties are described on the basis of sensor responses to nine different test analytes comprising volatile organic compounds, toxic gases, and chemical warfare agent simulants. The influence of the metal ion center and substituents on sensor selectivity and sensitivity is discussed. The compounds show good performance in the gas-sensing experiments with diverse responses to the analytes. Phthalocyanine species with pronounced selectivity for polar analytes, hydrocarbons or amines have been identified among the set of sensors with the help of multivariate data exploration methods. The results reveal that quite a high diversity in terms of selectivity is introduced through the minute variations to the phthalocyanine structure.

中文翻译：

---

3,4-二烷氧基苯基甲苯磺酰氨基取代酞菁的合成及QCM气敏性能

八取代的金属酞菁 [M = Ni(II)、Zn(II)、Co(II) 和 Cu(II)] 在外围位置带有 3,4-二烷氧基苯基甲苯磺酰氨基，由 1,2-二氰基合成4,5-之二[(3,4-二烷氧基苯基-甲苯磺酰基氨基)甲基]苯在相应的无水金属盐存在下。在金属离子中心旁边，二烷氧基苯基部分中烷基链的长度（n = 4, 5, 6, 和 12) 变化。总共有 16 种可溶性酞菁已通过元素分析、FT-IR 和1H-NMR光谱和质谱。此外，已经使用石英晶体微量天平传感器研究了这些新化合物的气体传感特性。传感特性是根据传感器对九种不同测试分析物的响应来描述的，这些分析物包括挥发性有机化合物、有毒气体和化学战剂模拟物。讨论了金属离子中心和取代基对传感器选择性和灵敏度的影响。这些化合物在气体传感实验中表现出良好的性能，对分析物有不同的反应。借助多变量数据探索方法，已在一组传感器中鉴定出对极性分析物、碳氢化合物或胺具有显着选择性的酞菁物种。