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https://doi.org/10.5562/cca3308

Synthesis of Fluorescent Diphenylanthracene-Based Calix[4]arene Derivatives and their Complexation with Alkali Metal Cations

Marina Tranfić Bakić ; Laboratory of Physical Chemistry and Corrosion, Faculty of Food Technology and Biotechnology, University of Zagreb, Pierottijeva 6, HR-10000 Zagreb, Croatia
Katarina Leko ; Division of Physical Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Nikola Cindro ; Division of Physical Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Tomislav Portada ; Laboratory of Supramolecular Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, Croatia
Tomica Hrenar ; Division of Physical Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Leo Frkanec ; Laboratory of Supramolecular Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, HR-10000 Zagreb, Croatia
Gordan Horvat ; Division of Physical Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Josip Požar ; Division of Physical Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Vladislav Tomišić ; Division of Physical Chemistry, Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia

Sažetak

Two novel fluorescent calix[4]arenes comprising diphenylanthracene moiety at the lower rim were synthetized and their complexation with alkali metal cations in acetonitrile/dichloromethane and methanol/dichloromethane mixtures (φ = 0.5) was studied experimentally and by classical molecular dynamics and quantum chemical calculations. The monosubstituted calixarene derivative (L1) proved to be a poor cation receptor, whereas the ester-based macrocycle (L2) exhibited rather high affinity towards lithium, sodium and potassium cations, particularly in MeCN/CH2Cl2. All complexation reactions were enthalpically controlled, whereby the overall stability was the largest in the case of sodium complex. The computational investigations provided an additional insight into the complexation properties and structures of complex species. The molecular dynamics simulations indicated the occurrence of inclusion of solvent molecules in the calixarene hydrophobic cavity of the free and complexed ligand, which was found to significantly affect the complexation equilibria.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Ključne riječi

calixarenes; diphenylanthracene; alkali metal cations; fluorescence; complexation; thermodynamics

Hrčak ID:

199329

URI

https://hrcak.srce.hr/199329

Datum izdavanja:

29.12.2017.

Posjeta: 1.681 *