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


Tranfić Bakić, Marina; Leko, Katarina; Cindro, Nikola; Portada, Tomislav; Hrenar, Tomica; Frkanec, Leo; Horvat, Gordan; Požar, Josip; Tomišić, Vladislav
Synthesis of Fluorescent Diphenylanthracene-Based Calix[4]arene Derivatives and their Complexation with Alkali Metal Cations // Croatica chemica acta, 90 (2017), 4; 711-725 doi:10.5562/cca3308 (međunarodna recenzija, članak, znanstveni)


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

Autori
Tranfić Bakić, Marina ; Leko, Katarina ; Cindro, Nikola ; Portada, Tomislav ; Hrenar, Tomica ; Frkanec, Leo ; Horvat, Gordan ; Požar, Josip ; Tomišić, Vladislav

Izvornik
Croatica chemica acta (0011-1643) 90 (2017), 4; 711-725

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Calixarenes, diphenylanthracene, alkali metal cations, fluorescence, complexation, thermodynamics
(Calixarenes, diphenylanthracene, alkali metal cations, fluorescence, complexation, thermodynamics.)

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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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