Phenazine and its fused derivatives, including polymers based on them, are widely used in various fields of science and technology, in particular, as materials for energy storage and transmission, building blocks for the synthesis of organic semiconductors, fluorophores, including fluorophores for thermally activated fluorescence, chemically/electrochemically controlled switches, electrophotochemically active materials, bio- and chemosensors, etc . In most cases, the synthesis of phenazine-containing polymers in solution is complicated by the low solubility of the reaction products. In this regard, methods that do not involve the use of solvents are of high demand. In this article, we wish to report a method for the preparation of two types of dibenzo[ a,c ]phenazine-containing polymers, such as polyazamethine and polyurea, using mechanosynthesis under a ball milling at 500 rpm. For this, two synthetic approaches were used. The first method involves the reaction of 4,4'-(dibenzo[ a,c ]phenazine-2,7-diyl)dianiline with terephthalaldehyde under acid catalysis at room temperature. The second method involves the reaction of 4,4'-(dibenzo[ a,c ]phenazine-2,7-diyl)dianiline with triphosgene in the presence of a base, potassium carbonate. The advantages of these methods are short reaction time (4 hours) and good product yields (up to 85%). The structure of the obtained polymers was confirmed by means IR-spectroscopy and 1H NMR-spectroscopy. In the IR-spectra of polyazamethine, there were no absorption bands of the carbonyl group of terephthalaldehyde and primary amino groups, while the absorption band of the azomethine fragment N=CH was presented. In the IR spectrum of polyurea, there was an absorption band of the carbonyl group of the urea moiety along with the absence of signals of primary amino groups. The 1H NMR spectra of the polymers contain proton signals from fragments of both types of monomer units. Using the end group analysis method, the number average molecular weights of the resulting polymers were determined.
Translated title of the contributionMECHANOSYNTHESIS OF AZA-LINKED DIBENZO[A,C]PHENAZINECONTAINING POLYMERS
Original languageRussian
Pages (from-to)102-107
Number of pages6
JournalБутлеровские сообщения
Volume73
Issue number2
DOIs
Publication statusPublished - 2023

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