Anil‐Synthese. 3. Mitteilung [1] Über die Darstellung von Styryl‐Derivaten aus methyl‐substituierten carbocyclischen Aromaten

Siegrist, A. E.; Liechti, P.; Meyer, Hans; Weber, K.

doi:10.1002/hlca.19690520836

Cited by 117 publications

(26 citation statements)

References 53 publications

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“…Compounds I-III were synthesized by standard techniques starting from 2,4,6-trimethylpyridine and adding the appropriate arms by Siegrist reaction [30,31] with the corresponding imine. IV was synthesized by coupling of the functional group based on a benzene core with 1,3-dibenzaldehyde under standard Wittig conditions [32] (see the Supporting Information).…”

Section: Methodsmentioning

confidence: 99%

Surface Noncovalent Bonding for Rational Design of Hierarchical Molecular Self‐Assemblies

Bléger¹,

Kréher²,

Mathevet³

et al. 2007

Angew Chem Int Ed

129

112

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Self-assembly is a promising bottom-up route towards atomically precise fabrication of functional systems.[1] Nanoporous networks [2] that can host guest molecules [3,4] were obtained on metal surfaces under ultrahigh vacuum. Various supramolecular chemistry approaches have been applied [5][6][7][8][9] to obtain thermally [10,11] or chemically controlled [12,13] polymorphs. The spontaneous formation of patterns with hexagonal, [14] porous honeycomb, [15,16] or KagomØ [17] geometries has been also observed at the solution/solid interface. [18,19] The topologies, as well as the drastic structural changes often induced by minute changes in molecular structure [20] or solvent, [21] are usually explained a posteriori on the basis of molecular symmetry, molecule-substrate interactions, and moleculemolecule interactions. Interdigitation of alkyl chains is an example of the last-named [15,16,22,23] which is of practical interest since it is specific to the surface and does not occur in the bulk of the solution. Surprisingly, close-packed epitaxy of n-alkanes on highly ordered pyrolytic graphite (HOPG) [24][25][26] has not yet inspired the design of molecular linker exploiting this behavior.Hence, we designed a new molecular unit acting as a functional linking group able to form strong surface-assisted intermolecular "clips" which, by interdigitation, strictly mimic the atomically precise organization of n-alkanes on HOPG. It forms the basis of a design strategy which parallels polymer chemistry in that mono-, bi-, and trifunctional clipbearing building blocks form noncovalent surface dimers, polymers, and two-dimensional (2D) networks, respectively. We can then chemically steer the organization of these entities themselves at a higher supramolecular level.The adsorption of n-alkanes on HOPG results in the formation of close-packed 2D lamellae of parallel-aligned rectilinear chains, oriented along the h100i direction of graphite [19,25,26] according to the Groszek model [24] (Figure 1 A). Organization of the adsorbed monolayers is driven by two main factors: The first is the correspondence between the zigzag alternation of methylene groups and the h100i direction of HOPG, with a stabilization energy of about 64 meV per methylene group.[27] The second is the parallel packing of alkane molecules, which, besides steric hindrance, results from a stabilization energy between nearest chains 4.1 apart. From theoretical estimations, [28] we can infer 2D crystallization energies on the order of 20-25 meV per pair of facing methylene groups.

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Section: Methodsmentioning

confidence: 99%

Surface Noncovalent Bonding for Rational Design of Hierarchical Molecular Self‐Assemblies

Bléger¹,

Kréher²,

Mathevet³

et al. 2007

Angew Chem Int Ed

129

112

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“…Although the oligomer route has the advantage of exact control of end-groups and molecular weight, it is extremely time-consuming for higher molecular weight polymers. Hence, we use the Siegrist [75,76] polycondensation technique, originally described by Kretzschmann and Meier [77,78], to obtain PPV blocks with exactly one aldehyde end-group. The subsequent attachment of the initiator to the rigid PPV block occurs via the nucleophilic attack of a Grignard reagent to the aldehyde group.…”

Section: Design and Synthesis Of A Photovoltaic Block Copolymermentioning

confidence: 99%

Supramolecular self-assembly and opto-electronic properties of semiconducting block copolymers

Boer

Stalmach

Hutten

et al. 2001

Polymer

248

231

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“…The protection of the aldehyde function was necessary for the selective Siegrist condensation [10,11] 8 ϩ 9 Ǟ 10. Thus, the conjugation in aldehyde 7a was extended by two styryl units which led to the aldehyde 10.…”

Section: Scheme 2 Preparation Of Functionalized Stilbenesmentioning

confidence: 99%

Pentadecamer 2,5-Dipropoxy-1,4-phenylenevinylene

Meier¹,

Ickenroth²

2002

Eur. J. Org. Chem.

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The conjugated, all‐(E)‐configured pentadecamer 2,5‐dipropoxy‐1,4‐phenylenevinylene 1j was prepared by a multistep synthesis on the basis of hydroquinone. The procedure consists of a general method for the repetitive extension of oligo(phenylenvinylene) chains by two styryl units (7a ⇄ 10 ⇄ 12 ⇄ 14). The relatively rigid oligomer 1j represents a molecular wire of about 100 Å. The absorption of 1j provides a proof for the convergence theory for electronic properties of conjugated oligomers with increasing number of repeat units. The corresponding conjugated polymer 1p with the same substitution matches the values which were extrapolated from the oligomer series 1a−1j. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

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Anil‐Synthese. 3. Mitteilung [1] Über die Darstellung von Styryl‐Derivaten aus methyl‐substituierten carbocyclischen Aromaten

Cited by 117 publications

References 53 publications

Surface Noncovalent Bonding for Rational Design of Hierarchical Molecular Self‐Assemblies

Surface Noncovalent Bonding for Rational Design of Hierarchical Molecular Self‐Assemblies

Supramolecular self-assembly and opto-electronic properties of semiconducting block copolymers

Pentadecamer 2,5-Dipropoxy-1,4-phenylenevinylene

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