A simple two‐step synthesis of a novel, fully aromatic ladder‐type polymer

Chmil, K.; Scherf, Ullrich

doi:10.1002/marc.1993.030140401

Cited by 81 publications

(36 citation statements)

References 11 publications

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“…[54,55] These also show blue-green luminescence (l max ¼ 478 nm and 484 nm) with some long wavelength emission in the solid state which is attributed to aggregates. Their EL efficiency is very low.…”

Section: Ladder-type Poly(para-phenylene)s (Lppps)mentioning

confidence: 96%

Oligomers and Polymers Based on Bridged Phenylenes as Electronic Materials

Grimsdale

Müllen

2007

Macromol. Rapid Commun.

191

154

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The synthesis, properties, and application in electronic devices of ladder and step‐ladder phenylene‐based oligomers and polymers are reviewed with an emphasis on control of properties by synthetic design. Bridged polyphenylenes can be prepared with a range of different amounts and types of bridges. Fully bridged polymers suffer the problem of incomplete formation of bridges during polymer analogous reactions. This problem is surmounted by the synthesis of regular stepladder polymers in which the monomers are well‐characterized oligo(ladder‐phenylene)s. By controlling the degree of bridging and thus the planarity of the polymer, its optical properties can be tuned. The optical and electronic properties can be further controlled by means of the type of bridges used.

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Section: Ladder-type Poly(para-phenylene)s (Lppps)mentioning

confidence: 96%

Oligomers and Polymers Based on Bridged Phenylenes as Electronic Materials

Grimsdale

Müllen

2007

Macromol. Rapid Commun.

191

154

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“…217,218 The synthesis was carried out through carbonyl olefination of functionalized poly(para-phenylene) with B 2 S 3 217,218 or through 217,218 The synthesis was carried out through carbonyl olefination of functionalized poly(para-phenylene) with B 2 S 3 217,218 or through…”

Section: Solution-mediated Synthesis Of Graphene Nanoribbonsmentioning

confidence: 99%

New advances in nanographene chemistry

et al. 2015

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Nanographenes, or extended polycyclic aromatic hydrocarbons, have been attracting renewed and more widespread attention since the first experimental demonstration of graphene in 2004. However, the atomically precise fabrication of nanographenes has thus far been achieved only through synthetic organic chemistry. The precise synthesis of quasi-zero-dimensional nanographenes, i.e. graphene molecules, has witnessed rapid developments over the past few years, and these developments can be summarized in four categories: (1) non-conventional methods, (2) structures incorporating seven- or eight-membered rings, (3) selective heteroatom doping, and (4) direct edge functionalization. On the other hand, one-dimensional extension of the graphene molecules leads to the formation of graphene nanoribbons (GNRs) with high aspect ratios. The synthesis of structurally well-defined GNRs has been achieved by extending nanographene synthesis to longitudinally extended polymeric systems. Access to GNRs thus becomes possible through the solution-mediated or surface-assisted cyclodehydrogenation, or "graphitization," of tailor-made polyphenylene precursors. In this review, we describe recent progress in the "bottom-up" chemical syntheses of structurally well-defined nanographenes, namely graphene molecules and GNRs.

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“…The synthesis of the single-stranded carbonyl-functionalized PPP-intermediate (4) via aryl-aryl homocoupling according to Yamamoto was described by Chmil and Scherf in two previous papers 7,12) . Completely soluble 2,5-benzoyl-substituted poly(para-phenylene)s 4 can be generated by polycondensation of 4,499-dialkyl-substituted 29,59-dibromoterephthalophenone monomers and possess number-average molecular weights up to 53 000 which corresponds to a degree of polymerization of A95.…”

Section: Resultsmentioning

confidence: 99%

“…However, the corresponding vinylene-bridged ladder polymers (3), so-called angular poly-(acene)s, have been synthesized, also via a "classical" synthetic sequence. The synthetic procedure involves, in this case, the aryl-aryl-coupling of an alkyl-substituted 29,59-dibromoterephthalophenone with Ni[0]-reagents 7) followed by a subsequent polymer-analogous olefination according to McMurry. Unfortunately, this class of conjugated ladder materials displays a drastically reduced quantum efficiency of photo-and electroluminescence when compared to the methylene-bridged system 1 8) .…”

Section: Introductionmentioning

confidence: 99%