Synthesis and characterization of copolyformals containing electron-rich or electron-poor porphyrin units in the mainchain and their use as sensors

tIn this study two new porphyrin monomers, 5,15-di(pentafluorophenyl)-10,20-di(p-hydroxyphenyl)-porphyrin and 5,15-di(pentabutoxyphenyl)-10,20-di(p-hydroxyphenyl)-porphyrin, were synthesizedand characterized by NMR and MALDI-TOF mass spectrometry. The chemical characteristics of thesemonomers are strongly influenced by their respective electronic distribution which, in turn, is determinedby the phenyl ring substituents. By reaction with different amounts of 1,20-di(bisphenoxy-A)-eicosanein presence of dibromomethane, copolyformals containing porphyrin dyes at different percentages weresubsequently obtained. The sensing responses of the synthesized copolymers were tested with the follow-ing analytes: acetic, trifluoroacetic and hydrochloridic acids and nitrogen dioxide. Our data indicate thatporphyrin units interact with analytes in a reversible fashion, it being understood that the decabuthoxyporphyrin derivative has a greater affinity than the other one with both acids and NO2.