| Name: | Description: | Size: | Format: | |
|---|---|---|---|---|
| 2.55 MB | Adobe PDF |
Advisor(s)
Abstract(s)
The synthesis of two new inherently chiral calix[4]arenes (ICCs, 1 and 2), endowed with electron-rich concave surfaces, has been achieved through the desymmetrization of a lower rim distal-bridged oxacyclophane (OCP) macrocycle. The new highly emissive ICCs were resolved by chiral HPLC, and the enantiomeric nature of the isolated antipodes proved by electronic circular dichroism (CD). Using time-dependent density functional calculations of CD spectra, their absolute configurations were established. NMR studies with (S)-Pirkle's alcohol unequivocally showed that the host-guest interactions occur in the chiral pocket comprehending the calix-OCP exo cavities and the carbazole moieties.
Description
Keywords
Absolute configuration assignment Calix[4]arenes Chiroptical properties Fluorescence POC-2014 Planar chirality TDDFT calculations
Citation
PRATA, José Virgílio Coelho; BARATA, Patrícia Alexandra David; PESCITELLI, Gennaro – Inherently chiral Calix[4]Arenes with planar chirality: Two new entries to the family. Pure and Applied Chemistry. ISSN: 0033-4545. Vol. 86, nr. 11 (2014), pp. 1819-1828
