Carboxylic acid functionalized ortho-linked oxacalix[2]benzene[2]pyrazine: synthesis, structure, hydrogen bond and metal directed self-assembly.

doi:10.1039/c2dt11283c

Paper

Carboxylic acid functionalized ortho-linked oxacalix[2]benzene[2]pyrazine: synthesis, structure, hydrogen bond and metal directed self-assembly.

Published Apr 10, 2012 · Lingwei Kong, Ming-Liang Ma, Liang-Chun Wu

Dalton transactions

Q1 SJR score

15

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

Cyclooligomerization of 2,6-dichloropyrazine 4 and benzyl 2,3-dihydroxybenzoate 5 under microwave irradiation resulted in a racemic pair of ester functionalized ortho-linked oxacalix[2]benzene[2]pyrazine 6, which was further transformed to the corresponding racemic carboxylic acid functionalized ortho-linked oxacalix[2]benzene[2]pyrazine 3. Both enantiomers of 3 adopt 1,3-alternate conformations with their two carboxylic acid groups pointing to opposite directions in the solid state. Enantiomers of 3 form a step-like one-dimensional supramolecular polymer via intermolecular hydrogen bond interactions between the carboxylic acids for crystals obtained in methanol. No hydrogen bonds were formed between the carboxylic acids for crystals of 3 obtained in pyridine and aqueous guanidine solutions; instead, intermolecular hydrogen bonds between the carboxylic acid groups of 3 and pyridine, as well as guanidinium ions were formed. Under metal-mediated self-assembly conditions, the pyrazinyl nitrogen atoms in 3 interacted with transition metal ions, such as Ag(I), Cu(II) and Zn(II), and resulted in the formation of four new metal-containing supramolecular complexes. Metallomacrocycles 7, 8 and 9 were formed by reactions of 3 with Ag(I) or Cu(II) ions by bridging two ligands 3 in the equatorial region via M-N coordination bonds. A one-dimensional coordination polymer 10 was generated by reaction between ligand 3 and Zn(II) ions, and a cage-based structure is presented in 10 by bridging of the cyclophane units by Zn(2+) ions via Zn-N and Zn-O bonds.

Study Snapshot

Carboxylic acid functionalized ortho-linked oxacalix[2]benzene[2]pyrazine can form one-dimensional supramolecular polymers and metal-containing supramolecular complexes when reacted with transition metal ions.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Carboxylic acid functionalized ortho-linked oxacalix[2]benzene[2]pyrazine: synthesis, structure, hydrogen bond and metal directed self-assembly.

Sign up to use Study Snapshot

References

Structures

This paper identifies three classes of plane graphs (J, K, and L) with constant metric dimensions, and shows that three vertices are a minimal requirement for unique identification of all vertices in these classes.

Coordination-driven self-assembly of discrete and polymeric copper(ii) and dicopper(ii) supramolecular structures based on oxacalix[2]benzene[2]pyrazines.

Oxacalix[2]benzene[2]pyrazines can form discrete and polymeric copper(ii) and dicopper(ii) supramolecular structures, with ligands acting as axial 2-connected nodes.

Synthesis and structure characterization of unsymmetrical oxacalix[2]benzene[2]pyrazines

Unsymmetrical oxacalix[2]benzene[2]pyrazines were synthesized and characterized, revealing highly distorted conformations and unique structures.

Coordination-driven self-assembly of a discrete molecular cage and an infinite chain of coordination cages based on ortho-linked oxacalix[2]benzene[2]pyrazine and oxacalix[2]arene[2]pyrazine.

Silver cations in oxacalix[2]benzene[2]pyrazine and oxacalix[2]arene[2]pyrazine form a discrete molecular cage and an infinite chain of coordination cages, respectively, with potential applications in cata

Efficient fragment coupling approaches toward large oxacalix[n]arenes (n = 6, 8).

This study demonstrates a rational, stepwise synthesis of large oxacalix[n]arenes (n = 6, 8) using a straightforward [3 + 3] fragment coupling approach, enabling facile synthesis of unsymmetrical oxacalix[4]- and oxacal

Citations

Tetracationic-to-dianionic tetraamino-dihydroxy-tetraoxacalix[4]arene: a paraquat receptor for all seasons

The tetraamino-dihydroxy-tetraoxacalix[4]arene 1 H 6 4+ 4Cl - is the most efficient paraquat receptor, with its conformational preferences influencing its stability in different ionization states.

Novel oxacalix[2]arene[2]triazines with thermally activated delayed fluorescence and aggregation-induced emission properties.

Oxacalixarenes show excellent thermally activated delayed fluorescence properties and aggregation-induced emission properties in THF/H2O mixtures.

Thiophene-based porous organic networks for volatile iodine capture and effectively detection of mercury ion

Thiophene-based porous organic networks effectively capture volatile iodine and effectively detect mercury ion in ethanol-water solutions.

Review on the Synthesis of Pyrazine and Its Derivatives

Synthesis of pyrazine and its derivatives has been developed using various synthetic approaches, mainly for flavor and pharmaceutical applications.

Tetranitro-oxacalix[4]crown-Based Host-Guest Recognition Motif and a Related [2]Rotaxane-Based Molecular Switch.

This study developed a tetranitro-oxacalix[4]crown/urea host-guest recognition motif and a related [2]rotaxane-based molecular switch, enabling reversible translocation between secondary ammonium binding sites and urea binding