A New Approach for the Design of Supramolecular Recognition Units:  Hydrogen-Bonded Molecular Duplexes

Gong, Bing; Yan, Yuli; Zeng, Huaqiang; Skrzypczak-Jankunn, Ewa; Kim, Yong Wah; Zhu, and Jin; Ickes, Harold

doi:10.1021/ja990904o

Cited by 193 publications

(115 citation statements)

References 21 publications

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“…Im- Conformational constraints based on H···O interactions: An alternative conformationally restricting element, which is commonly used to bias the conformation of aromatic amides, is based on ortho-alkoxy substitution. The resulting interaction between neighboring hydrogen and O atoms leads to a wide variety of foldamer structures reported over the past years; [19][20][21] however, they are solely restricted to amide connectivities. To see whether a triazole-derived aromatic foldamer strand would gain additional stabilization by introducing ortho-alkoxy substituents, various alkylated resorcinol derivatives were linked by means of the click reaction.…”

Section: Conformational Constraints Based On H···n Interactionsmentioning

confidence: 99%

“…Therefore, compound 22 also seems to adopt an Scheme 5. Synthesis of resorcinol-triazole-resorcinol model compounds 21-23 with R = C 6 H 13 (21,22) and CH 3 (23), shown in their preferred anti-anti conformations.…”

Section: Conformational Constraints Based On H···n Interactionsmentioning

confidence: 99%

“…as compared to the parent nonsubstituted 1-phenyl-1,2,3-triazoles (d CÀN = 1.429 as well as 1.443 ). [21,22] The maximum benefit of these structural motifs would be gained when different building blocks, which possess their distinct conformational properties, could be combined in a construction kit principle and any desired foldamer shape could be afforded consequently. For this purpose, mixed systems that comprised a central BTP unit with terminal orthoalkoxy-substituted phenyl moieties were synthesized.…”

Section: Conformational Constraints Based On H···n Interactionsmentioning

confidence: 99%

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Designing Structural Motifs for Clickamers: Exploiting the 1,2,3‐Triazole Moiety to Generate Conformationally Restricted Molecular Architectures

Zornik

Meudtner

Malah

et al. 2010

Chemistry A European J

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Noncovalent interactions, especially hydrogen-bonding interactions as well as electrostatic forces, confined within one macromolecule are the key to designing foldamers that adopt well-defined conformations in solution. In the context of significant recent activities in the area of triazole-connected foldamers, so-called clickamers, we present a fundamental study that compares various model compounds that bear adjacent N-, O-, or F-heteroatom substituents. The interplay of attractive and repulsive interactions leads to rotational constraints around the single bonds attached to both the 1- and 4-positions of the 1,2,3-triazole moiety and should therefore be able to induce well-defined conformational preferences in higher oligomers and polymers, that is, foldamers. Various compounds were synthesized and characterized with regard to their preferred conformations in all three aggregation states--that is, in the gas phase, in solution as well as in the solid state--by employing DFT calculations, NMR spectroscopic experiments, and X-ray crystallography, respectively. On the basis of the thus-obtained general understanding of the conformational behavior of the individual connection motifs, heterostructures were prepared from different motifs without affecting their distinct folding characteristics. Therefore, this work provides a kind of foldamer construction kit, which should enable the design of various clickamers with specific shape and incorporated functionality.

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Section: Conformational Constraints Based On H···n Interactionsmentioning

confidence: 99%

Section: Conformational Constraints Based On H···n Interactionsmentioning

confidence: 99%

Section: Conformational Constraints Based On H···n Interactionsmentioning

confidence: 99%

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Designing Structural Motifs for Clickamers: Exploiting the 1,2,3‐Triazole Moiety to Generate Conformationally Restricted Molecular Architectures

Zornik

Meudtner

Malah

et al. 2010

Chemistry A European J

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“…[29][30][31][32][33][34][35][36][37] For example, oligoamides represented by general structure 1 have a self-complementary H-bonding sequence that direct the formation of H-bonded duplexes 1$1 (Scheme 1). A study on the ability of 1$1 to template chemical reactions led to the discovery on the gelation of nonpolar, aromatic hydrocarbons by duplexes carrying appropriate alkyl side chains.…”

Section: -28mentioning

confidence: 99%

Amphiphilic oligoamides as versatile, acid-responsive gelators

et al. 2017

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Six oligoamides with the same backbone but different side and end chains, G1-G6, were designed and synthesized. Screening the gelating abilities of these oligoamides revealed G2 as a versatile gelator capable of forming stable hydrogels as well as several organogels. From UV, fluorescence, NMR, and SEM studies, the formation of hydrogels is driven by hydrophobic forces and p-p stacking while the gelation of nonpolar organic solvents relies on hydrogen-bonding interactions. The hydrogel of G2 is able to encapsulate and release medicinally important polar substances into water with acidresponsiveness.

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“…[29] Molecular modelling of compound 21 ( Figure 5, left) and 12 (see Figure S4 in the Supporting Information) reveals that in both compounds only a bifurcated hydrogen bond between both NH donor groups of the C-linked amino acids and the ArCO acceptor unit is formed in spite of the fact that in the tri-pseudopeptide 12 a second CO acceptor group is also present. This explains the relatively high dimerization constant shown by 21 (nearly double that of 20) and the large downfield shift ∆δ = 1.4 ppm of the NHCbz proton observed upon 21 2 dimer formation.…”

Section: Conformational and Self-assembly Properties Of Nclinked Pepmentioning

confidence: 99%

Self‐Assembled Chiral Dimeric Capsules from Difunctionalized N,C‐Linked Peptidocalix[4]arenes: Scope and Limitations

et al. 2008

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In this paper we report the synthesis of the first examples of upper (wide) rim calix [4]arene amino acids 5 and 27, together with the conformational, self-assembly and molecular inclusion properties of the N,C-linked peptidocalix[4]arenes obtained from them. Whereas the dipropyl derivative 5 readily undergoes peptide synthesis allowing a small library of calix[4]arene pseudopeptides 12-21 to be obtained, the tetrapropoxy compound 27 preferentially gives upper-rimbridged derivatives (e.g., 28) which are formed through an intramolecular condensation reaction. The tetrapropoxycalix[4]arene pseudopeptide 33 shows conformational and self-assembly properties quite different to those of the dipropoxy derivatives 12-21. The observed differences are explained on the basis of the different conformational flexibilities of the two calix[4]arene scaffolds. Calixarene 5 is more rigid than 27 thanks to the presence of two OH groups at the lower (narrow) rim that are involved in strong intramolecular hydrogen bonds. Only peptidocalix[4]arenes 12-21 but not

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A New Approach for the Design of Supramolecular Recognition Units: Hydrogen-Bonded Molecular Duplexes

Cited by 193 publications

References 21 publications

Designing Structural Motifs for Clickamers: Exploiting the 1,2,3‐Triazole Moiety to Generate Conformationally Restricted Molecular Architectures

Designing Structural Motifs for Clickamers: Exploiting the 1,2,3‐Triazole Moiety to Generate Conformationally Restricted Molecular Architectures

Amphiphilic oligoamides as versatile, acid-responsive gelators

Self‐Assembled Chiral Dimeric Capsules from Difunctionalized N,C‐Linked Peptidocalix[4]arenes: Scope and Limitations

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