Self-Assembly Mediated by the Donor−Donor−Acceptor·Acceptor−Acceptor−Donor (DDA·AAD) Hydrogen-Bonding Motif:  Formation of a Robust Hexameric Aggregate

Kolotuchin, Sergei; Zimmerman, Steven C.

doi:10.1021/ja981862r

Cited by 113 publications

(66 citation statements)

References 7 publications

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“…Such secondary hydrogen bonds were also found in other supramolecular, multiple hydrogen bonded systems described for example in ref. [10,14,15] The configuration where the hydrogen atom is located between three electronegative atoms, being covalently bound to one and hydrogen bonded to the other two, is also referred to as three-center hydrogen bonds. Examples of these have been well established by the neutron diffraction studies of the amino acids and the pyranose sugars.…”

Section: Resultsmentioning

confidence: 99%

“…33), 132(12), 116(12), 104(14),76 (18); HR-MS: calcd for C 26 H 20 N 6 O 2 : 448.1648; found: 448.1655; elemental analysis calcd (%) for C 26 H 20 N 6 O 2 : C 69.64, H 4.46, N 18.75; found C 69.48, H 4.61, N 18.59.N,N',N''-Tris(-(3',5'-dimethylphenyl)benzene-1,3,5-tricarbonamide (6 b): A solution of 1,3,5-benzenetricarbonyl trichloride (0.99 g, 3.71 mmol) in dry CH 2 Cl 2 (20 mL) was added dropwise to a solution of 3,5-dimethylaniline (1.35 g, 11.16 mmol) and triethylamine (2.5 mL) in dry CH 2 Cl 2 (70 mL). After complete addition, the mixture was stirred at room temperature for 24 h. The reaction mixture was treated with water (100 mL), stirred for 20 min and the resulting precipitate was filtered.…”

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confidence: 99%

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Molecular Recognition of Carbohydrates by Artificial Receptors: Systematic Studies towards Recognition Motifs for Carbohydrates

Mazik

Sicking

2001

Chem. Eur. J.

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The synthesis and binding properties for carbohydrates of several artificial, acyclic receptors containing two or three heterocyclic recognition units covalently attached to a phenyl spacer is described. These host molecules having uncharged hydrogen-bonding sites were used in a systematic study towards the evaluation of recognition motifs for carbohydrates. A novel effective, acyclic hydrogen-bonding receptor possessing naphthyridine-amide moieties as heterocyclic recognition units has been developed.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Molecular Recognition of Carbohydrates by Artificial Receptors: Systematic Studies towards Recognition Motifs for Carbohydrates

Mazik

Sicking

2001

Chem. Eur. J.

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“…When an aggregate is in equilibrium with its free components, extensive tailing may occur, and well-defined peaks can only be obtained if dissociation is negligible. [63] When aggregates of different aggregation number are in dynamic equilibrium with each other, the equilibrium is concentration-dependent, and the elution behavior of aggregates at the front and back of the elution band is different from those at the center of the elution band. Only when the equilibrium is between a small number of different aggregates, analysis of the chromatographic behavior is feasible.…”

Section: Coils Rods and Rings In Hydrogen-bonded Supramolecular Polymentioning

confidence: 99%

Coils, Rods and Rings in Hydrogen‐Bonded Supramolecular Polymers

Cate

Sijbesma

2002

Macromol. Rapid Commun.

163

117

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The article discusses the development and properties of supramolecular polymers based on quadruple hydrogen bonds between self‐complementary ureidotriazine (UTr) and ureidopyrimidinone (UPy) functional groups. The high association constant with which these groups dimerize leads to polymers with a high degree of polymerization in isotropic solution. Application of these units for the functionalization of telechelic polymers results in new materials with mechanical properties approaching those of covalent polymers, but with a much stronger temperature‐dependent behavior. Solvophobic interactions between the hydrogen bonding moieties may be used to obtain supramolecular polymers with a well defined helical columnar architecture. Another consequence of the high dimerization constant of the UPy group is the phenomenon of a critical concentration in solutions of many bifunctional monomers. Below this concentration, only cycles are present, while above the critical concentration, the amount of cycles remains constant, and a polymer is formed. Conformational properties of the linker units are used to control the equilibrium between polymers and cycles, and are proposed to form a promising strategy toward tunable materials.Supramolecular polymer material with elastomeric properties resulting from functionalization with UPy groups. (Reproduced with permission. © John Wiley & Sons, Inc.)magnified imageSupramolecular polymer material with elastomeric properties resulting from functionalization with UPy groups. (Reproduced with permission. © John Wiley & Sons, Inc.)

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“…The non-covalent interactions such as ion pairing, hydrogen bonding and p-p stacking are observed in these ionic compounds. We have particularly aimed to investigate 'hydrogen bonding' interactions, which have received a special interest in different fields because of their directional and precise nature [17][18][19][20]. We have also regarded the 'p-p stacking' interaction as a remarkable feature of some of our crystalline systems, as it has been considered as an effective factor on stability of biological and chemical systems [21][22][23][24][25].…”

Section: Introductionmentioning

confidence: 99%

Different complexation behavior of a proton transfer compound obtained from 1,10-phenanthroline and pyridine-2,6-dicarboxylic acid with InIII and CeIII: Synthesis, crystal structures and solution studies

Ramezanipour¹,

Aghabozorg²,

Shokrollahi

et al. 2005

Journal of Molecular Structure

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The different complexation methods of a proton transfer compound LH 2 , (phenH) 2 (pydc) (phenZ1,10-phenanthroline; pydcH 2 Z pyridine-2,6-dicarboxylic acid), are discussed and formation of [In 2 SO 4 (pydc) 2 (phen) 2 (H 2 O) 2 ]$5.5H 2 O (1) and {[Ce(pydc)(pydcH)(H 2 O) 2 ] $4H 2 O} n (2) are reported. The complexes were synthesized by reaction of LH 2 with In 2 (SO 4 ) 3 $xH 2 O and Ce(NO 3 ) 3 $6H 2 O, respectively. The characterization was performed using IR spectroscopy and X-ray diffraction. The complex 1 crystallizes in the space group P 1 of the triclinic system, with two molecules per unit cell. The unit cell parameters are aZ11.9547(6) Å , bZ12.8482(7) Å , cZ16.1313(8) Å , aZ89.532(1)8, bZ72.007(1)8 and gZ68.066(1)8. The crystal system of the complex 2 is monoclinic with space group P2 1 /c and four molecules per unit cell. The unit cell parameters are aZ14.0273(8) Å , bZ11.2184(6) Å , cZ12.9441(8) Å and bZ102.177(5)8. The complex 1 is a binuclear mixed-ligand system in which both phen and (pydc) 2K have contributed to the molecular structure as tri-and bi-dentate ligands, respectively. The complex 2 is a polymeric system in which only one of the fragments of LH 2 has acted as a ligand. In both complexes 1 and 2 a large number of hydrogen bonds are observed. These interactions especially in case of complex 2 play an important role in the formation of self associated systems in the crystal lattices. Results of the potentiometric pH titration studies in aqueous solution strongly confirm the formation of In III and Ce III complexes in solution with stoichiometries very similar to those of the crystalline complexes 1 and 2, respectively.

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Self-Assembly Mediated by the Donor−Donor−Acceptor·Acceptor−Acceptor−Donor (DDA·AAD) Hydrogen-Bonding Motif: Formation of a Robust Hexameric Aggregate

Cited by 113 publications

References 7 publications

Molecular Recognition of Carbohydrates by Artificial Receptors: Systematic Studies towards Recognition Motifs for Carbohydrates

Molecular Recognition of Carbohydrates by Artificial Receptors: Systematic Studies towards Recognition Motifs for Carbohydrates

Coils, Rods and Rings in Hydrogen‐Bonded Supramolecular Polymers

Different complexation behavior of a proton transfer compound obtained from 1,10-phenanthroline and pyridine-2,6-dicarboxylic acid with InIII and CeIII: Synthesis, crystal structures and solution studies

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