Binding of HSO4– vs proton transfer in aminophenyl-substituted adamantane dipyrromethane receptors (CROSBI ID 574337)
Prilog sa skupa u zborniku | sažetak izlaganja sa skupa | međunarodna recenzija
Podaci o odgovornosti
Alešković, Marija ; Došlić, Nađa ; Basarić, Nikola ; Mlinarić-Majerski, Kata
engleski
Binding of HSO4– vs proton transfer in aminophenyl-substituted adamantane dipyrromethane receptors
Molecular recognition of anion species by neutral pyrrole receptors is a continuing challenge in the field of anion coordination chemistry.1 We have recently investigated adamantane-dipyrromethanes as potential anion binding agents.2 Our next step was introduction of a chromofore into the binding site, as in I, so that receptors could be employed as chromogenic or fluorogenic sensors. We report the synthesis and anion binding studies of new receptors 1-4 with F–, Cl–, Br–, AcO–, H2PO4–, HSO4–, NO3– in CH3CN by UV/Vis and fluorescence spectrometry. Compared to 1 and 2, receptors 3 and 4, respectively, were expected to form more stable complexes with anions due to the introduction of hydrogen bond donor, amino moiety. However, UV/Vis and fluorescence titrations indicated higher association constants only for HSO4–. That prompted us to investigate whether the obtained values correspond to association constants of the complexes, or proton transfer equilibrium between the HSO4– and NH2 as reported by Bowman-James.3 Therefore we performed a thorough 1H NMR, UV and fluorescence study in the presence of an acid and/or HSO4–. Further, the geometry, energetics and protonation state of the complexes have been investigated at the DFT level using the dispersion-corrected wb97xD functional4 combined with the polarization continuum model.
proton transfer; pyrrole receptors; UV/Vis and fluorescence spectrometry;
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Podaci o prilogu
2011.
objavljeno
Podaci o matičnoj publikaciji
6-ISMSC - International Symposium on Macrocyclic and Supramolecular Chemistry, Brighton, United Kingdom
Brighton:
Podaci o skupu
6-ISMSC - International Symposium on Macrocyclic and Supramolecular Chemistry
poster
03.07.2011-07.07.2011
Brighton, Ujedinjeno Kraljevstvo