Циклофани, що містять фрагменти флуоренонів, зв’язаних жорсткими бічними стінками

R&D registration number in UkrISTEI: 0120U100122

What priority area of ​​science and technology does it correspond to: fundamental scientific research on the most important problems of developing scientific, technical, socio-economic, socio-political, human potential to ensure Ukraine’s competitiveness in the world and sustainable development of society and the state.

Research: fundamental.

Source of funding: funds from the state budget.

Prospect for further implementation in 2021-2022: continued as fundamental.

Research level: no analogues in Ukraine.

Patent: no.

What additional actions require further research: additional funding, modern scientific equipment.

Brief description, advantages, further prospects for application.

Using the MMFF molecular mechanics method, molecular modeling of 3 fluorenonophanes, differing in the position of the methylene groups and the method of addition of benzene rings (p- and m-isomers, respectively), was carried out. A conformational search showed that the syn- and anti-conformations of cyclophanes, which differ in the orientation of the carbonyl groups, are the most favorable. Both conformers have an open intramolecular cavity. The geometric parameters of syn- and anticonformers are determined. It has been shown that the width between the fluorenone fragments for the compound with meta-addition of benzene rings is extremely small (for the syn-conformer, the width is less than two van der Waals radii of the carbon atom), which may indicate the absence or extremely low stability of the complexes of this “host” with guest molecules. The range of potential “guest” molecules was determined and their volumes were calculated. All cyclophanes are rectangular in shape, and the guest molecules entering the host cavity must be placed parallel to the fluorenone fragment and stabilized due to π-π stacking interactions. Benzene fragments can additionally stabilize the inclusion complex, but the main stabilization should occur due to the fluorenone fragment. The synthesis of fluorenonophanes was carried out by the interaction of 2,7-bis(bromomethyl)-9H-fluoren-9-one with 2,7-bis(p-oxyphenoxymethylene)fluoren-9H-2-one (15%) or resorcinol (7%) under the conditions high dilution of reagents in DMF in the presence of K2CO3. The research carried out relates to the field of supramolecular chemistry and corresponds to the world level.

More details…