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O-aminofenol i poli(O-aminofenol) - właściwości i zastosowanie

Marczewska B., Przegaliński M.

Wiadomości Chemiczne

2009

[Z] 63, 11-12

1115-1143

From the chemical and electrochemical points of view aminophenol isomers are a group of compounds which can exhibit the properties typical of both the amines and/or phenols [1.5]. The position of the amine group and hydroxyl group in the aromatic ring is decisive to determine different properties of particular isomers. As concerns the chemical properties, including the ability to form electroactive films, out of the ortho, meta [6, 7] and para [6, 8, 9] isomers of aminophenol the o-aminophenol (oAP) seems to be the most important. The paper presents the process of chemical [12.16] and electrochemical [20.32] oxidation of oAP based on literature data. The products of chemical oxidation are: 2-aminophenoxasin-3-one of quinone diimine and quinones. As a result of the process of electrochemical oxidation of oAP many products were obtained, depending on conditions in which the process was carried out. For the oAP polymer were proposed: the ladder network structure of closed type, the structure with partially open ring, or simultaneous co-existence of both these structures. The preparation of polymer film from poly(o-aminophenol) (PoAP) as well as its structure and properties were also described. The preparation of PoAP film of determined structure depends largely on conditions in which the electropolymerization process is performed and also on the purity of oAP used as initial substrate [62, 63]. The electrochromic properties of the film depend on the potential applied in the course of electrode process, pH, and the kind of electrolyte anions [27, 58]. The potential range of electrical conductivity was also discussed, as well as transport across modified PoAP electrodes [71.74] and electrodeposition of metals on modified PoAP electrodes [75.77]. The paper presents some applications of oAP and PoAP, such as the modification of Amberlite XAD-2 resin [51], production of actinomycin D [52.57], or possibilities of their application in electrodes [80.86] and as anti-corrosion coating [88]. oAP is an important organic compound also in view of its impact on a living organism. Therefore some biochemical properties of oAP such as the metabolism of oAP in human erythrocytes [36.40] or the damage of DNA due to oAP [41.45] could not be omitted.