Bioorganic Chemistry of Rigid-Rod Molecules: Adventures with p-Oligophenyls

Baudry, Yoann Cyril; Baumeister, Bodo; Das, Gopal; Gérard, David; Matile, Stefan; Sakai, Naomi; Som, Abhigyan; Sordé, Nathalie; Talukdar, Pinaki

doi:10.2533/000942902777679948

Cited by 6 publications

(3 citation statements)

References 18 publications

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“…These devices emit light in the entire visible range and even provide polarized light under the appropriate conditions. Moreover, this class of molecules has been proven to act as useful rigid‐rod cores for liquid‐crystalline materials29 and as amphiphilic materials for biological applications 30. Conceptually, organic compounds provide many advantages compared to inorganic materials, in particular the ability of fine‐tuning the properties of the material through functional group manipulation.…”

Section: Introductionmentioning

confidence: 99%

Surface‐Confined Self‐Assembly of Di‐carbonitrile Polyphenyls

Klyatskaya

Klappenberger

Schlickum

et al. 2011

Adv Funct Materials

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This Feature Article reports on the controlled formation and structurefunctionality aspects of vacuum-deposited self-assembled organic and metal-organic networks at metal surfaces using ditopic linear and nonlinear molecular bricks, namely di-carbonitrile polyphenyls. Surface confi ned supramolecular organization of linear aromatic molecules leads to a fascinating variety of open networks. Moreover, cobalt-directed assembly of the same linear linkers reveals highly regular, open honeycomb networks with tunable pore sizes representing versatile templates for the organization of molecular guests or metal clusters and the control of supramolecular dynamers. In addition, the 2D nanopore organic networks act as arrays of quantum corrals exhibiting confi nement of the surface-electronic states of the metallic substrate. A reduction of the linker symmetry leads to the formation of disordered, glassy coordination networks, which represent a structural model for amorphous materials.

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Section: Introductionmentioning

confidence: 99%

Surface‐Confined Self‐Assembly of Di‐carbonitrile Polyphenyls

Klyatskaya

Klappenberger

Schlickum

et al. 2011

Adv Funct Materials

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“…1). Previous reviews related to this topic emphasize barrel-stave supramolecules, 1 bioorganic chemistry of rigid-rod molecules, 2 structural 3 and functional plasticity 4 of rigid-rod b-barrels, and rigid push-pull rods. 5 Research on synthetic multifunctional pores became possible with the discovery of synthetic routes to artificial b-barrels, 1,6 which, in turn, became accessible with the introduction of rigidrod molecules in bioorganic chemistry.…”

Section: Introductionmentioning

confidence: 99%

Synthetic multifunctional pores: lessons from rigid-rod β-barrels

2003

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In this account, studies on synthetic multifunctional pores formed by rigid-rod beta-barrels are summarized comprehensively. The first section outlines the evolution of synthetic multifunctional pores from the introduction of rigid-rod molecules in bioorganic chemistry and the discovery of synthetic beta-barrels in comparison with pertinent developments in related areas of research. Design strategies to position active sites at the inner surface of rigid-rod beta-barrel pores are described in the second section. The third section focuses on the characteristics of transmembrane barrel-stave pores, emphasizing the dynamic nature of supramolecular oligomers with the aid of notional phase and energy diagrams. Section four introduces multifunctionality with the use of synthetic pores as hosts of a rich collection of guests, reaching from inorganic cations to organic macromolecules like peptides, oligonucleotides, polysaccharides and polyacetylenes. In section five, practical applicability of molecular recognition by synthetic multifunctional pores is documented with non-invasive fluorometric enzyme sensing. The application of host-guest chemistry within synthetic pores to couple molecular recognition and translocation with molecular transformation is the topic of section six. The last section mentions some perspectives and challenges with synthetic multifunctional pores.

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“…Barrel-stave supramolecule 1, however, is not a traditional enzyme mimic. It is a rigidrod β-barrel with a hydrophobic outer surface (provided by leucine residues) and a hydrophilic inner surface (provided by partially protonated histidine residues) [2]. In water, rigid-rod β-barrel 1 exists -like certain biogenic β-barrel pores -as a slightly soluble prepore that inserts spontaneously into bilayer membranes to form active pores.…”

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confidence: 99%