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Poly(arylene ethynylene)s: From Synthesis to Application

Christoph Weder (eds.)

Resumen/Descripción – provisto por la editorial

No disponible.

Palabras clave – provistas por la editorial

Polymer Sciences; Organic Chemistry; Characterization and Evaluation of Materials; Analytical Chemistry

Disponibilidad
Institución detectada Año de publicación Navegá Descargá Solicitá
No detectada 2005 SpringerLink

Información

Tipo de recurso:

libros

ISBN impreso

978-3-540-23366-4

ISBN electrónico

978-3-540-31570-4

Editor responsable

Springer Nature

País de edición

Reino Unido

Fecha de publicación

Información sobre derechos de publicación

© Springer-Verlag Berlin Heidelberg 2005

Cobertura temática

Tabla de contenidos

Synthesis and Structure of PAEs

Uwe H. F. Bunz

This review discusses the progress in the synthesis of poly(aryleneethynylene)s (PAEs). It covers the literature from 1999 through 2003. The last comprehensive review of PAE synthesis appeared in 2000. The present review comprehensively updates the developments in the synthesis of PAEs. Synthetic methods are discussed first, followed by the description of PAEs with novel structures and topologies. Progress has been made in the field of water-soluble and bioavailable poly(-phenyleneethynylene)s (PPEs) and in the field of heterocyclic PAEs. In the last section the polymer-analogous reactions of PAEs are treated. Reduction and metal complexation are discussed. Most of the novel PAEs are proposed for applications in “plastic electronics” and/or in sensors.

Pp. 1-52

Organometallic PAEs

Elisabeth Klemm; Thomas Pautzsch; Lars Blankenburg

This review describes recent results in the field of poly(aryleneethynylene)s (PAEs) that contain metal ions in the polymer backbone, or in the polymer side chain. This work is focused primarily on polymers possessing ligands of metal complexes as part of the aryleneethynylene chain. PAEs with porphyrinylene in the backbone have also been addressed. Synthetic routes toward the polymers, as well as their photochemical, photophysical, and electrochemical properties, are presented. Monodisperse oligo(phenyleneethynylene)s with terminal metal complexes or with a ferrocene and thiol at each end are mentioned.

Pp. 53-90

Supramolecular Organization of Foldable Phenylene Ethynylene Oligomers

Jeffrey S. Moore; Christian R. Ray

This review summarizes the supramolecular organization of foldable phenylene ethynylene (PE) oligomers and polymers. -Phenylene ethynylenes (PEs) have demonstrated the ability to undergo a cooperative, solvophobic collapse from a random conformation into a compact helical structure. The stability of this compact structure can be altered through modification of various nonspecific and specific interactions. A result of the solvophobic collapse of the mPE backbone is the formation of a solvophobic cavity where small-molecule guests may bind with some measure of specificity. Use of chiral guests or chiral moieties in the backbone or side chains can lead to a bias of the handedness of the helical form. Further supramolecular organization was observed in solution in the form of higher order aggregates and at the air–water interface. In the solid state it was found that PE packing was dependent on the stability of the folded state. Application of these folding principles to imine-containing PEs allowed for the biasing of combinatorial libraries toward the most stable folded state or host–guest complex, as well as the formation of high molecular weight polymers. Strategies for creating water-soluble PEs are also explored. The theoretical groundwork for the emerging field of -phenylene ethynylenes (PEs) will also be discussed.

Pp. 91-149

Poly(arylene ethynylene)s in Chemosensing and Biosensing

Timothy M. Swager; Juan Zheng

Poly(arylene ethynylene)s (PArEs) have been used in recent years as effective transducers for a variety of sensing purposes ranging from organic molecules such as methyl viologen and TNT to biological analytes. Their superior sensitivity to minor perturbations is fundamentally governed by the energy transport properties resulting from the extended conjugation of the polymer backbone. An understanding of the underlying principles of energy transport allows the design of sensors with greater sensitivity and specificity. Pioneering work with methyl viologen as an electron-transfer quencher demonstrated that connecting receptors in series amplifies the sensing response compared to that of individual receptors. Since then, factors such as the electronic and structural nature of the polymers and their assembly architecture have proven to be important in improving sensory response. In this review, we present an overview of works to date by various groups in the field of PArE chemosensors and biosensors.

Pp. 151-179

PAEs with Heteroaromatic Rings

Takakazu Yamamoto; Isao Yamaguchi; Takuma Yasuda

This article reviews the synthesis and chemical properties of poly(aryleneethynylene)s, PAEs, consisting of sulfur-containing heteroaromatic rings (e.g., thiophene), nitrogen-containing heteroaromatic rings (e.g., pyridine), and silicon-containing heteroaromatic rings (e.g., silole). The polymers are usually prepared via Pd-catalyzed C–C coupling between diethynyl compounds and dihalo organic compounds. However, synthesis using other monomers such as distannylacetylenic compounds is also possible. This article describes the chemical and optical properties of PAEs, which are affected by the basic electronic properties of the heteroaromatic ring and the molecular structure of the PAE.

Pp. 181-208

Electronic Properties of PAEs

Christoph Weder; Gabriela Voskerician

Poly(arylene ethynylene)s (PAEs) represent an important family of conjugated polymers with interesting optical and electronic properties. A great deal of attention has been devoted to the synthesis, physicochemical characteristics, and optical properties of these materials, but their electrically (semi)conducting nature has received comparably little attention. Only during the last decade have significant research efforts been devoted to this subject in research laboratories around the world, and PAEs have eventually established themselves as a versatile class of polymeric semiconductors. Focusing on the subjects of electrical conductivity, charge transport, and electroluminescence, this review article attempts to provide a comprehensive summary of the electronic properties of PAEs and their potential applications in “plastic electronic” devices.

Pp. 209-248