The synthesis of two new inherently chiral calixarenes (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.
|Autori:||Prata, José V. ; Barata, Patrícia, D.; Pescitelli, Gennaro|
|Titolo:||Inherently chiral calixarenes with planar chirality: two new entries to the family|
|Anno del prodotto:||2014|
|Digital Object Identifier (DOI):||10.1515/pac-2014-0707|
|Appare nelle tipologie:||1.1 Articolo in rivista|