АЛКИЛИРОВАНИЕ САМООРГАНИЗОВАННЫХ КОМПЛЕКСОВ НА ОСНОВЕ ПИРИДИН-3-БОРОНОВОЙ КИСЛОТЫ
Електронний архів E-archive DonNTU – (Electronic archive Donetsk National Technical University)
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| Title |
АЛКИЛИРОВАНИЕ САМООРГАНИЗОВАННЫХ КОМПЛЕКСОВ НА ОСНОВЕ ПИРИДИН-3-БОРОНОВОЙ КИСЛОТЫ
ALKYLATION OF SELF-ASSEMBLING COMPLEXES BASED ON PYRIDINE-3-BORONIC ACID |
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| Creator |
Савсуненко, Александр Олегович
Широкородова, Юлия Александровна Карпичев, Евгений Адольфович Попов, Анатолий Федорович Matondo, Hubert Rico-Lattes, Isabelle Lattes, Armand |
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| Subject |
алкилирование
ковалентные органические каркасы пиридин-3-бороновая кислота бороксин alkylation covalent organic frameworks pyridine-3-boronic acid boroxine |
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| Description |
Получена и охарактеризована супрамолекулярная структура – пентадекамер пиридин-3-бороновой кислоты. Изучено его строение, устойчивость и способность к образованию N-алкилпроизводных. Избирательное алкилирование пентадекамера йодалканами приводит к образованию нового типа амфифилов моно- и триалкилзамещеных бороксинов пиридин 3 бороновой кислоты, а в случае 1,10-дийоддекана и 1,2-бис(2-йодэтокси)этана позволяет получить димерные структуры – прекурсоры ковалентных органических каркасов
Over the recent decades, designing novel materials became a promising challenge in chemistry. The covalent-organic frameworks (COF) are one of the most remarkable new synthetic materials with nanoporous structure that could be used for gas storage, fuel cells design, in the catalysis, optoelectronics, etc. Most of boron-containing COF are built by means of N→B bonding which makes boronic acids among the important precursors of COFs. N-Alkyl derivatives of pyridine-3-boronic have been recently reported to be functionalized surfactants low aggregation concentration very low pKa. Pyridine-3-boronic acid contains in its structure both boron and nitrogen atoms which makes it a prospective building unit for COF. A novel cage supramolecular structure, pentadecamer of pyridine-3-boronic acid, was obtained and characterized. Its structure in crystal was investigated using X-ray crystallography; 1H and 13C NMR spectroscopy was used for study in the solution. This structure consists of 15 pyridine-3-boronic acid monomers with 10 N→B bonds; the cage diameter was shown to be 5Å. The supramolecular complex was shown to remain stable with heating up to 95 oC in DMSO-d6 whereas in D2O CD3OD the monomer of pyridine-3-boronic acid appeared. The ability of the pentadecamer to form N-alkyl derivatives was studied. Its selective alkylation with iodoalkanes leads to formation of monosubstituted (methanol)) and trisubstituted (chloroform) boroxines of pyridine-3-boronic acid. These new compounds are expected to be еру amphiphiles exhibiting a wide variety of unusual aggregation properties. In the case of 1.10-diiododecane and 1.2-bis(2-iodoethoxy)etnane, the alkylation allows us to obtain dimeric structures which supposed to be the precursors of 3D covalent-organic frameworks. |
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| Date |
2013-04-11T15:47:59Z
2013-04-11T15:47:59Z 2013 |
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| Type |
Article
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| Identifier |
2074-6652
УДК 547.63:547.7:547.8 http://ea.donntu.edu.ua/handle/123456789/18406 |
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| Relation |
Наукові праці ДонНТУ;Серія: Хімія і хімічна технологія, 2013. - Вип.1(20). - С.119-127
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| Publisher |
Донецк, ДонНТУ
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