Calixporphyrin - a New Type of Porphyrinoid Container Molecule

Abstract

An efficient synthetic route from anthracene to calixporphyrin, a new type of porphyrinoid container molecule is described. The rigid framework of defined size and high symmetry of calixporphyrins represent interesting properties for molecular recognition and catalysis.

Toward Isolated Molecular Wires: A pH-Responsive Canopied Polypyrrole

“…Notable examples include triptycene-type pyrroles that afforded rigid biconcave porphyrins after condensation with suitable aldehydes and subsequent oxidation. 42,43 The pyrrolic fragments in these conformationally well-defined compounds and their analogues were accessed either by reduction and subsequent hydrolysis 42,43 of dinitriles or by reactions between deprotonated R-isocyanoesters and electron-deficient olefins. [44][45][46][47][48] In addition to increasing the structural dimensionality of the planar precursor, installation of polycyclic skeletons on the β-positions of pyrrole enhances chemical stability by suppressing the activation of exocyclic C-H bonds or electrophilic attack on the pyrrole ring.…”

“…Sterically hindered pyrrole derivatives having polycyclic backbones have precedents in porphyrin literature. Notable examples include triptycene-type pyrroles that afforded rigid biconcave porphyrins after condensation with suitable aldehydes and subsequent oxidation. , The pyrrolic fragments in these conformationally well-defined compounds and their analogues were accessed either by reduction and subsequent hydrolysis 42,43 of dinitriles or by reactions between deprotonated α-isocyanoesters and electron-deficient olefins. − …”

Synthetic receptors

“…Kräutler has described the efficient synthesis of a porphyrinoid container molecule, "calixporphyrin", from anthracene and studied its ability to bind a selection of amines. 175…”