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Registration Number

0224U033385, (0122U000344) , R & D reports

Title

Synthesis and complexing properties of bis(benzocrown ethers) with a rigid linker that reorganizes crown ether cycles to interact with substrates

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Синтез вихідних бензокраун-етерів та оксизаміщених бензокраун-етерів. Розробка ефективного методу отримання нових біс(бензокраун-етерів) з фрагментами конденсованих дифенілхромонів. Дослідження взаємодії синтезованих краун-сполук з органічними і неорганічними субстратами. Вивчення впливу розміру циклів краун-етерів на процесс комплексоутворення. Оцінка перспективності використання синтезованих сполук в якості хемосенсорів.

Head

Kyrychenko Tetiana I., Доктор хімічних наук

Registration Date

26-12-2024

Organization

Physico-Chemical Institute O. Bogatsky National Academy of Sciences of Ukraine

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Synthesis of new bis(benzocrown ethers) with a rigid linker based on diphenylcumaranocoumarone, which binds crown ether cycles. Study of their structure and properties. Investigation of the processes of formation of guest-host complexes of synthesized molecular tweezers with guest molecules.

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The object of the research – The reaction of hydroxybenzocrown ethers with benzil, leading to the formation of diphenylcoumaranocoumarones. Complexing properties of bis(benzocrown ethers) containing coumarone moietiy that links crown ether rings. The purpose of the work – synthesis of new bis(benzocrown ethers) with a rigid linker based on diphenylcoumaranocoumarone, which connects crown ether rings. Study of their structure and properties. Investigation of the processes of formation of guest-host complexes of synthesized molecular tweezers with guest molecules. Molecular tweezers with fragments of benzocrown ethers and diphenylcoumaranocoumarone were synthesized by prolonged (96 h) heating of hydroxybenzocrown ethers and benzil at 60 °C in a mixture of acetic and hydrochloric acids with the addition of chloroform. The expected compounds were obtained as stable clathrates with acetic acid. The pure products were isolated by column chromatography on silica gel, eluent chloroform-methanol, 10:1. The complexation of the obtained bis(crown ethers) with alkali and alkaline earth metal cations and salts of aliphatic diamines was studied by spectrophotometric titration. With alkali metal cations, complexes of only 1:1 composition are formed. The obtained stability constants values do not allow us to reliably attribute the structure of intramolecular sandwiches to the complexes. With alkaline earth metal cations, complexes of composition 1:1 are formed, the stability constants of which indicate the participation in the interaction of only one crown ether cycle. Very stable 2:1 ligand:metal complexes are also formed. All diamines studied form 1:1 complexes with bis(crown ether)s with 18-membered crown ether rings. The stability constants values of the complexes indicate that only one crown-ether cycle participates in the interaction. The stability of 2:1 complexes is higher than that of 1:1 complexes by 2-4 orders of logarithmic units.

Product Description

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Bohashchenko Tetiana Yu.
Kyrychenko Tetiana I.
Kulyhina Kateryna Yu.
Yakovenko Iryna S.