Conformationally switchable non-cyclic tetrapyrrole receptors: synthesis of tetrakis(1H-pyrrole-2-carbaldehyde) derivatives and their anion binding properties.

@article{Deliomeroglu2014ConformationallySN,
  title={Conformationally switchable non-cyclic tetrapyrrole receptors: synthesis of tetrakis(1H-pyrrole-2-carbaldehyde) derivatives and their anion binding properties.},
  author={Murat K. Deliomeroglu and Vincent M Lynch and Jonathan L. Sessler},
  journal={Chemical communications},
  year={2014},
  volume={50 80},
  pages={
          11863-6
        }
}
A series of tetrakis(1H-pyrrole-2-carbaldehyde) receptors (2, 4, and 6) were synthesized in two steps from commercially available starting materials. The anion binding properties of these receptors can be tuned through electronic switching to stabilize a conformation displaying high affinity for the dihydrogenphosphate and pyrophosphate anions (as the tetrabutylammonium salts) in chloroform. 
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References

SHOWING 1-10 OF 19 REFERENCES
Synthesis and anion binding studies of o-phenylenevinylene-bridged tetrapyrrolic macrocycle as an expanded analogue of calix[4]pyrrole.
An o-phenylenevinylene-bridged tetrapyrrolic macrocycle (2) was synthesized by means of a Horner-Wadsworth-Emmons reaction between benzylbisphosphonate and SEM-protected diformylpyrrole, followed byExpand
2-amidopyrroles and 2,5-diamidopyrroles as simple anion binding agents.
TLDR
Four new 2-amidopyrroles and 2,5-diamidopirroles have been synthesized and their anion complexation properties investigated and hydrogen bonding in the solid state leading to dimer and network formation is revealed. Expand
Fluorinated Calix[4]pyrrole and Dipyrrolylquinoxaline: Neutral Anion Receptors with Augmented Affinities and Enhanced Selectivities
The use of the 3,4-difluoro-1H-pyrrole as a building block for the preparation of octamethyloctafluorocalix[4]pyrrole and 2,3-di(3‘,4‘-difluoropyrrol-2‘yl)quinoxaline is described. These latter twoExpand
A Scalable Synthesis of Meso-Substituted Dipyrromethanes
A one-flask synthesis of meso-substituted dipyrromethanes has been refined. The procedure entails reaction of an aldehyde in 100 equiv of pyrrole as the solvent containing a mild Lewis acid (e.g.,Expand
The syntheses and structures of Group 1 expanded dipyrrolides: the formation of a 12-rung amidolithium circular ladder
Elaboration of meso-disubstituted dipyrromethanes to incorporate imino or amino donors results in ligands that adopt unique, aggregated structures with Group 1 metals.
One-flask synthesis of meso-substituted dipyrromethanes and their application in the synthesis of trans-substituted porphyrin building blocks
Abstract The reaction at room temperature of an aldehyde with excess pyrrole in the absence of solvent affords the meso-substituted dipyrromethane. The reaction is catalyzed with trifluoroacetic acidExpand
Single side strapping: a new approach to fine tuning the anion recognition properties of calix[4]pyrroles.
TLDR
It is postulated that not only cavity size per se, but also the ability of the aryl portion of the strap to serve as a CH hydrogen bond donor site are important in regulating the observed anion affinities. Expand
Quantification of nitrate-π interactions and selective transport of nitrate using calix[4]pyrroles with two aromatic walls.
TLDR
The "two-wall" aryl-extended calix[4]pyrroles show excellent activity in ion transport through lipid-based lamellar membranes and are highly selective for transport of nitrate over other anions. Expand
Anion Receptor Chemistry
Review: advances in anion complexation and application of receptors in organocatalysis and nanotechnology; 57 refs.
An Introduction to Hydrogen Bonding
1. Brief History 2. Nature and Properties 3. Strong Hydrogen Bonds 4. Moderate Hydrogen Bonds 5. Weak Hydrogen Bonds 6. Cooperativity, Patterns, Graph Set Theory, Liquid Crystals 7. Disorder, ProtonExpand
...
1
2
...