Metalloporphyrin-Capped Calix[4]pyrroles:  Heteroditopic Receptor Models for Anion Recognition and Ligand Fixation

Diametrically strapped calix[4]pyrrole−metalloporphyrin conjugates, potential hosts for anionic guests, have been synthesized and characterized. The syntheses rely on the acid-catalyzed condensation of two dipyrromethane bearing Ni(II) porphyrins with acetone. An 1H NMR spectroscopic titration exper...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2005-04, Vol.70 (8), p.3148-3156
Main Authors: Panda, Pradeepta K, Lee, Chang-Hee
Format: Article
Language:English
Subjects:
Anions - chemistry
Calixarenes
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Magnetic Resonance Spectroscopy
Metalloporphyrins - chemical synthesis
Metalloporphyrins - chemistry
Models, Chemical
Molecular Structure
Nickel - chemistry
Organic chemistry
Porphyrins
Preparations and properties
Pyrroles - chemistry
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Diametrically strapped calix[4]pyrrole−metalloporphyrin conjugates, potential hosts for anionic guests, have been synthesized and characterized. The syntheses rely on the acid-catalyzed condensation of two dipyrromethane bearing Ni(II) porphyrins with acetone. An 1H NMR spectroscopic titration experiment indicated that the resulting receptors selectively trapped fluoride anions in organic media but not other, larger halide anions. The experimental results from titration and Job plots indicated that the bound fluoride anion must reside inside the cavity. The current systems provide a well-defined illustration of how size-selective anion receptors may be synthesized by incorporating recognition functions, such as Lewis acidity, hydrogen bonding, and encapsulating moieties into established recognition motifs, calix[4]pyrrole in the present instance.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo047993u