Effects of the Addition ofOrtho- andPara-NH₂Substituted Tetraphenylporphyrins on the Structure of Nylon 66

Abstract

The synthetic tetrapyrrole macrocycles, such as porphyrins (H2P) and phthalocyanines (H2Pc), exhibit interesting physicochemical properties suitable to be used in modern technology. For many applications, those species should be trapped or fixed inside graphite, hydrotalcites, silica, TiO2, or polymers. Methodologies for the optimization of the properties of porphyrins, trapped or fixed inside polymers, have been barely developed. Our research works in the development of methodologies for the optimization of incorporation and display of properties of tetrapyrrole macrocycles inside inorganic, polymeric, or hybrid networks. This paper shows some results about the effect of the spatial disposition of the amine (–NH2) groups attached on the periphery of substituted tetraphenylporphyrins, on the Nylon 66 structure and on the display of the physicochemical properties of the trapped macrocycles. Nylon 66 was synthesized from adipoyl chloride and hexamethylenediamine in presence of tetraphenylporphyrins substituted with –NH2groups localized at theortho- orpara-positions of the phenyls. Cobalt complexes formation was used to quantify the amount of porphyrins in the polymer fibers. Characterization results show that the spatial position of amine groups of the porphyrins has important structural and textural effect on the Nylon 66 fibers and on the fluorescence of the porphyrins integrated into the fibers.

Transport of Protons and Capacitive Properties of the Nylon/Porphyrin/Graphene Oxide Coating

“…The combined presence of GO and porphyrins, in combination with electrospinning times present variable behavior in the impedance data obtained (table 1). This is possibly due to the difficulty of aggressive species diffusing through the tortuous coating paths, because of the physical barrier of the nylon and GO, and the electrical property of the porphyrins and GO that maintain the aggressive hydrogen ions over the surface, making difficult to reach the substrate [27,28].Characterization results show that the spatial position of amine groups of the porphyrins has important structural and textural effect on nylon and porphyrins integrated into the fibers.…”

“…As it is well known, porphyrin macro-cycles are tetra-dentate form complexes with most metals [28].The number and spatial position of the amine groups(-NH2) at the ortho-and parapositions of phenyls of tetraphenyl porphyrins, incorporated during polymerization can produce different modified nylon networks. The use of different species apparently induces the formation of a more homogeneous but rougher porous matrix than that of the H2T(o-NH2)PP species.…”

“…The use of different species apparently induces the formation of a more homogeneous but rougher porous matrix than that of the H2T(o-NH2)PP species. The existence of four central nitrogens in the porphyrin macro-cycle makes the synthesis of metal complexes possible; these systems are suitable to be used with other cations such as transition metals for different applications such as electrochemical or supercapacitors [1,27,28]. …”

Nylon/Porphyrin/Graphene Oxide Fiber Ternary Composite, Synthesis and Characterization

“…In this sense, the bands at around 20.47˚ and 23.56˚ correspond to the reflection of attributed to a slightly crystallinity increment induced by the incorporation of the porphyrin in the polyamide network [32].…”

“…All the above mentioned tests suggest a chemical interaction between the different materials that make up the compound, in the case of the species ny-lon/H 2 T(p-NH 2 )PP the polymerization occurs in such a way that it starts or ends on the four peripherals -NH 2 groups, connected and located in the same molecular plane of H 2 T(p-NH 2 )PP, forming nylon chains at the periphery of the macrocycle [32]. In the presence of H 2 T(p-NH 2 )PP the polyamide chain formation take place faster; this polymerization is favored due to the lower basicity Figure 13.…”