Conjugated Polymers from Naphthalene Bisimide

Guo, Xugang; Watson, Mark D.

doi:10.1021/ol801918y

Cited by 325 publications

(346 citation statements)

References 31 publications

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“…Thus, appropriately coupled di- [26a, 43] and tetrasubstituted [44] NDI derivatives could be obtained by Suzuki, Stille, or Sonogashira coupling. This approach found wide application, particularly for the synthesis of conjugated oligomers [45] and polymers, [46] which enabled donor-acceptor polymers to be created for organic electronics applications. The conjugative interactions of electron-poor NDI with appropriate electron-rich donor units can result in low band gap polymers.…”

Section: Core Functionalization With Nucleophilesmentioning

confidence: 99%

Strategies for the Synthesis of Functional Naphthalene Diimides

2014

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Naphthalene diimides, which have for a long time been in the shadow of their higher homologues the perylene diimides, currently belong to the most investigated classes of organic compounds. This is primarily due to the initial synthetic studies on core functionalization that were carried out at the beginning of the last decade, which facilitated diverse structural modifications of the naphthalene scaffold. Compounds with greatly modified optical and electronic properties that can be easily and effectively modulated by appropriate functionalization were made accessible through relatively little synthetic effort. This resulted in diverse interesting applications. The electron-deficient character of these compounds makes them highly valuable, particularly in the field of organic electronics as air-stable n-type semiconductors, while absorption bands over the whole visible spectral range through the introduction of core substituents enabled interesting photosystems and photovoltaic applications. This Review provides an overview on different approaches towards core functionalization as well as on synthetic strategies for the core expansion of naphthalene diimides that have been developed mainly in the last five years.

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Section: Core Functionalization With Nucleophilesmentioning

confidence: 99%

Strategies for the Synthesis of Functional Naphthalene Diimides

2014

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“…[34] PNIBT was effectively synthesized by Stille coupling polymerization using Pd 2 (dba) 3 /P(o-tolyl) 3 as catalyst, similar to our previous report for a related analogue. [35] The molecular weight of PNIBT, determined by gel permeation chromatography relative to polystyrene standards, was 113 kDa with a polydispersity index of 3.33. Contrary to variable temperature optical absorption measurements (see below), differential scanning calorimetry (DSC) scans of PNIBT indicated no obvious thermal transitions, up to 350 8C (Fig.…”

mentioning

confidence: 99%

High‐mobility Ambipolar Transistors and High‐gain Inverters from a Donor–Acceptor Copolymer Semiconductor

et al. 2010

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“…Oxygen has a smaller van der Waals radius (1.5Å) compared to the methylene group (2.0Å), and additionally there is a favorable electrostatic attraction between oxygen and the neighboring thienyl sulfur atoms). This has been shown to help planarize the head-to-head alkoxy linkages [90,91], and may also explain the ability of the 5-bromo-3-alkoxy-2-thienyl magnesium chloride to polymerize (unlike the alkyl isomer 3), as the initiation of polymerization requires a reduction of the Ni(II) by dimerization of the thienyl Grignard. It is important to note that the use of 2-bromo-3-alkoxythiophene, in analogy to the McCullough method for poly(3-alkyl)thiophene, does not afford regioregular polymers [86].…”

Section: Thiophene-based Monomersmentioning

confidence: 99%

The Synthesis of Conjugated Polythiophenes by K umada Cross‐Coupling

Koch

Heeney

2012

Materials Science and Technology

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Conjugated polymers have been the subject of intensive research efforts over the past few decades. Much of this interest has stemmed from the fact that such materials combine the inherent processibility and mechanical robustness associated with polymers, with the electronic properties more typically associated with inorganic semiconductors. Thus, such materials may allow the fabrication of electronic devices on a variety of flexible or conformable surfaces, by a range of potentially low-cost and large-area deposition techniques such as printing. Possible applications include field effect transistors for display backplanes, organic solar cells, electrochromic displays, chemical sensors, and polymeric light-emitting diodes [1].Within the realms of conjugated polymer research, thiophene-containing materials have been one of the most widely investigated classes for many of the above applications [2,3]. Thiophene is a cheap and widely available electron-rich, planar aromatic heterocycle which is readily functionalized by range of chemistries. As a result, it can be copolymerized with a variety of aromatic comonomers to generate polymers with extended π-electron delocalization along the backbone. The alternating double and single bonds of the delocalized conjugated system are nondegenerate, leading to an energy band gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO). For many of the optoelectronic applications outlined above, the absolute energy levels of the HOMO and LUMO, as well as the band gap between them, are important parameters affecting device performance. As such, major research efforts have been devoted to understanding how chemical structure can influence the electronic delocalization of conjugated polymers. Whilst these factors are complex, they can be related to points such as the attachment of electron-donating/-withdrawing substituents to the polymer backbone, the degree of backbone planarity (and, therefore, the π-electron overlap and delocalization), and the nature and aromaticity of any comonomers included in the polymer backbone.

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Conjugated Polymers from Naphthalene Bisimide

Cited by 325 publications

References 31 publications

Strategies for the Synthesis of Functional Naphthalene Diimides

Strategies for the Synthesis of Functional Naphthalene Diimides

High‐mobility Ambipolar Transistors and High‐gain Inverters from a Donor–Acceptor Copolymer Semiconductor

The Synthesis of Conjugated Polythiophenes by K umada Cross‐Coupling

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