Журнал "Макрогетероциклы"

Elena V. Lukovskaya,^a@ Anastasia A. Kosmacheva,^a Yulia A. Sotnikova,^a Olga A. Fedorova,^a,b Alla A. Bobylyova,^a Yury V. Fedorov,^a,b Alexander V. Dolganov,^b and Aleksander V. Anisimov^a

^аChemistry Department, M.V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation

^bA.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119991 Moscow, Russian Federation

^@Corresponding author E-mail: luchal2006@yandex.ru

DOI: 10.6060/mhc150978l

Macroheterocycles 2016 9(1) 89-95

One of intensively developing direction in supramolecular chemistry is the creation of functional ensembles based on organic molecules. Prime examples of such ensembles are the complexes of viologens with crown ether in which the movement or disintegration – self-assembly of pieces under the influence of chemical or photochemical impulses occurs. Viologens – 1,1’-disubstituted-4,4’-bispyridinium salts – are widely used in the synthesis of novel materials due to their electron-deficient nature and excellent electrochemical characteristics. There are many systems based on viologens investigated by now. Among them guest-host complexes, sensors, molecular machines, prototypes of solar cells, electrochromic materials exist. Thiophene derivatives are important components of materials of optoelectronic devices. They are used in the construction of solar cells, LEDs, organic conductors. Obtaining of molecules with high electron mobility (important for optoelectronic devices) is achieved by the combination of donor and acceptor fragments. In particular, the molecules containing thiophene and viologen fragments in their composition demonstrate good characteristics. To obtain the systems combining the thiophene and viologen fragments we have used a supramolecular method of creation of psevdorotaxane complexes based on dibenzo-24-crown-8 ether, containing 3,4-ethylenedioxythiophene, and N,N’-dimethyl-4,4’-bipyridinium perchlorate. Thiophene derivatives have an ability to give an electron to form sufficiently stable cation radicals under the photoirradiation; viologens are the electron acceptors. In the complex they are located in close distance to each other for the exchange of electrons between these components, and it is important that the location of the excited states energy levels of the molecules allows them to exchange electrons or energy. It was shown earlier that dibenzo-24-crown-8 ether forms 1:1 complex with N,N’-dimethyl-4,4’-bipyridinium hexafluorophosphate in the acetone solution. Wherein, additionally to N-O coordination, the interaction between benzene rings of crown ether and pyridinium rings of viologen was found. It was interesting to determine the effect of thiophene-containing residue in crown ether on the complexation process.

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