Synthesis of a fully unsaturated all-carbon ladder polymer

Schlüter, A. Dieter; Löffler, M.; Enkelmann, Volker

doi:10.1038/368831a0

Cited by 115 publications

(69 citation statements)

References 11 publications

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“…Rigid rods (Scheme 4), for example on the basis of cyclobutadienylcobalt-linked butadiyne, [35] or the soluble carbon rods with a persilylethinylated polytriacetylene backbone [36] are, due to their complete conjugation, not only of interest for photonic applications [37] but can also be seen as precursors for the synthesis of carbon networks and grids. [40] Ladder polymers (Scheme 5 ) with a completely conjugated structure, known as "molecular boards", have been synthesized by repetitive Diels-Alder reaction and subsequent polymer analogous dehydration by Schliiter et al [41] Similar ladder structures containing phthalocyanine units which only need to be dehydrated to become fully aromatic have also been reported. [39] In an extension of dimensionality, a material with a 3-dimensional adamantane core and four poly- benzobisoxazole rod-like arms has been synthesized and discussed as a reinforcing component for polymers.…”

Section: Macromolecular Systems With Special Molecular Geometrymentioning

confidence: 99%

“…[35,38] Analogous networks are formed ( Figure 2) through the self organization of six tritropic linear ligands with bipyridinium structural elements and nine silver ions which leads to the formation of a supramolecular 3 x 3 lattice. [42] All-carbon ladder polymers, as discussed by Schliiter, [41] are structurally related to fullerenes in that they represent the circular belt region of c 6 0 . [40] Ladder polymers (Scheme 5 ) with a completely conjugated structure, known as "molecular boards", have been synthesized by repetitive Diels-Alder reaction and subsequent polymer analogous dehydration by Schliiter et al [41] Similar ladder structures containing phthalocyanine units which only need to be dehydrated to become fully aromatic have also been reported.…”

Section: Macromolecular Systems With Special Molecular Geometrymentioning

confidence: 99%

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Macromolecular chemistry and physics 1994

1995

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Section: Macromolecular Systems With Special Molecular Geometrymentioning

confidence: 99%

Section: Macromolecular Systems With Special Molecular Geometrymentioning

confidence: 99%

Macromolecular chemistry and physics 1994

1995

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“…Following this idea, many authors have proposed molecular wires composed of repeated units ͑oligomers͒ and tried to synthesize them by controlling the number of units added per stage. [6][7][8][9][10][11][12] But questions remain about this abundant list of molecules, for example: How is a given single oligomer connected electrically to the pads? Can a given conjugated oligomer show better conductance than another one of the different chemical structure?…”

Section: Introductionmentioning

confidence: 99%

Conductance and transparence of long molecular wires

1997

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Electron tunneling through a molecular wire is studied as a function of the length and chemical structure of the molecule. The current intensity is calculated using the electron-scattering quantum-chemistry technique, the wire being connected at both ends to a planar metal-vacuum-metal nanojunction. The tunnel channels and the stepped I(V) characteristics are discussed in detail for the oligo ͑thiophene ethynylene͒ molecular wire. At low bias voltage, the conductance G of a metal-molecular wire-metal junction follows a GϭG 0 e Ϫ␥L law with L the interelectrode separation. The inverse damping length ␥ depends on the internal wire electronic structure and the contact conductance G 0 on the electrode-wire end interactions. Both ␥ and G 0 can be optimized by changing the chemical structure of the wire, and are given for a large number of oligomers.

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“…Alternatively, Diels-Alder polyaddition is used for ladder polymers with well-defined structures using bifunctional components with both diene and dienophile functionalities. 125,126 Another problem of the ladder polymer synthesis is the difficult polymer characterization due to poor solubility, as has been shown during the solid-state polymerization of diacetylene derivatives. [127][128][129] We adopted alkylenediammonium disorbate monomers as the candidate for a bifunctional diene monomer for ladder polymer synthesis through topochemical polymerization.…”

Section: Ladder Structurementioning

confidence: 99%

Polymer Structure Control Based on Crystal Engineering for Materials Design

Matsumoto

2003

Polym J

111

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ABSTRACT:In this review article, polymer structure control and organic material design based on polymer crystal engineering are described. The structures and properties of crystalline materials are designed using pre-organized molecules through various intermolecular interactions such as hydrogen bonds, π · · · π, CH/π, CH/O, and halogen interactions. Here, we describe the features and mechanisms of the topochemical polymerization of 1,3-diene monomers including some ester, ammonium, and amide derivatives of muconic and sorbic acids, which are 1,3-diene di-and monocarboxylic acid derivatives, respectively. We have proposed the topochemical polymerization principles for diene monomers on the basis of the crystallographic data accumulated for various kinds of diene monomers. The combination of several intermolecular interactions is useful for the construction of molecular packing appropriate for 5 Å stacking in order to facilitate the topochemical polymerization in the crystalline state. We refer to the control of polymer chain structure including tacticity, molecular weight, and ladder structure, and also polymer crystal structures, as well as the organic intercalation system using layered polymer crystals obtained by the topochemical polymerization. A totally solvent-free system for the synthesis of layered polymer crystals is also described.KEY WORDS Topochemical Polymerization / Solid-State Reaction / Crystal Engineering / Supramolecular Synthon / Stereoregular Polymer / Controlled Radical Polymerization / X-Ray Single Crystal Structure Analysis / Intercalation / Controlled polymer synthesis, including the control of polymer chain structures such as molecular weight, molecular weight distribution, chain-end structure, branching, regioselectivity, and stereoselectivity, has great potential for the design of macromolecular architecture leading to advanced nano-materials and devices. [1][2][3][4][5][6][7][8][9][10][11] All the features and functions of polymers importantly depend on primary chain structures and the manner of polymer chain assembly in crystalline and non-crystalline solids, or in a condensed state. Therefore, the control of polymer chain structures in polymer synthesis can hardly be overestimated for the architecture of advanced polymeric materials.Especially, the stereochemistry of polymers has received significant attention in both fundamental and applied fields ever since the first discoveries of stereoregular polymers in the 1950s. 12-14 Highly controlled stereospecific polymerization has been well established by coordination polymerization of olefins and diene monomers and by anionic polymerization of certain types of polar monomers. Radical polymerization is the most important and convenient process for the production of various kinds of vinyl and diene polymers due to recent achievements in well-controlled polymerizations in addition to the classical advantages of the radical process. [15][16][17][18][19][20][21][22] There are two fundamentally different ways to control of the chain structu...

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Synthesis of a fully unsaturated all-carbon ladder polymer

Cited by 115 publications

References 11 publications

Macromolecular chemistry and physics 1994

Macromolecular chemistry and physics 1994

Conductance and transparence of long molecular wires

Polymer Structure Control Based on Crystal Engineering for Materials Design

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