Synthetic routes to bridged dicyclooctatetraenes and alkynylcyclooctatetraenes

Siesel, David A.; Staley, Stuart W.

doi:10.1021/jo00079a036

Cited by 18 publications

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“…This offers a novel approach to substituted COTs; for example, treatment of p -(dicubyl)benzene ( 13 ) and m -(dicubyl)benzene ( 14 ) with Rh 2 (1,5-cyclooctadiene) 2 Cl 2 provides p -(dicyclooctatetraenyl)benzene ( 15 ) and m -(dicyclooctatetraenyl)benzene ( 16 ), respectively, each in better than 85% yield. This approach is entirely different from previous modes of access to these compounds …”

mentioning

confidence: 93%

Building with Cubane-1,4-diyl. Synthesis of Aryl-Substituted Cubanes, p-[n]Cubyls, and Cubane-Separated Bis(arenes)¹

et al. 1999

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On treatment with an organolithium 1,4-diiodocubane generates cubane-1,4-diyl, a highly reactive species, shown here to be a versatile precursor to numerous aryl substituted cubanes, available now for the first time in high yield. The diyl is demonstrated to provide a good route to bicubyl and its derivatives. A kind of “living polymerization” of the diyl is developed to give the p-[n]cubyls. These oligomers are rigid rods made up of cubanes linked together at the 1 and 4 positions, each cubane adding ∼4.15 Å to the length. The properties of these rods, some more than 15 Å long, are discussed, as are methods for modifying their solubility. X-ray crystallographic analyses of some of these compounds are presented, with emphasis on packing parameters.

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confidence: 93%

Building with Cubane-1,4-diyl. Synthesis of Aryl-Substituted Cubanes, p-[n]Cubyls, and Cubane-Separated Bis(arenes)¹

et al. 1999

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“…Because of the low boiling point and great hazard of ( E )–1,2‐dichloroethene, the kind of synthetic route is almost not used in laboratory. In route (c), DAE unit is synthesized through Stille reaction between aryl bromide and ( E )–1,2‐bis(tributylstannyl)ethene . The kind of synthetic method is always utilized in the synthesis of DAE‐based polymers .…”

Section: Typical Synthetic Methods Of Dae‐based Building Blocks and Pmentioning

confidence: 99%

Rational design of diarylethylene‐based polymeric semiconductors for high‐performance organic field‐effect transistors

Zhang

2016

J. Polym. Sci. Part A: Polym. Chem.

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Constructing planar, rigid, and high electronically delocalized p-conjugated molecular system is the most basic requirements of obtaining high-performance polymeric semiconductors for organic field-effect transistors (OFETs). In this regard, diarylethylene (DAE)-based polymers show great potential because many substantive progresses related to polymer field-effect transistors had been achieved from the kind of polymer materials in recent years. In the brief review, series of DAE-based polymer are highlighted, based on which several design strategies have been summarized by the way of comparative research method. These strategies have important guiding significance not only for further developing new DAEbased and other polymeric semiconductors for OFETs but also for developing specific polymeric semiconductors for other organic electronics, such as organic photovoltaics and organic light-emitting diodes. V C 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 585-603 KEYWORDS: design strategies; diarylethylene; organic fieldeffect transistors; polymeric semiconductors; synthesis INTRODUCTION Solution-processable semiconducting polymers have attracted great interest during the recent decades because of the traits of excellent film forming property, and adjustable chemical structure and property, as well as the potential to fabricate various lightweight and flexible electronic devices such as organic field-effect transistors (OFETs) via cost-effective large-area graphic printing processes.

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“…1,4-Dicyclooctatetraenyl-1,3-butadiyne (1). Ethynylcyclooctatetraene (0.82 g, 6.4 mmol) and 1.69 g (15.1 mmol) of cupric acetate were dissolved in 6.0 mL of pyridine and 7.0 mL of methanol. This mixture was stirred overnight under a slightly positive pressure of O 2 and then taken up in 75 mL of hexane and washed with 3 × 50 mL of 6 M aqueous HCl and 3 × 50 mL of brine.…”

Section: Methodsmentioning

confidence: 99%

Kinetics of Bond Shift and Charge Transfer in Dialkynylphenylene-Bridged Dicyclooctatetraenes and Their Dianions

et al. 1999

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1,4-Dicyclooctatetraenyl-1,3-butadiyne and p-, m-, and o-di(cyclooctatetraenylethynyl)benzene (1−4, respectively) and their dipotassium salts (1 2-−4 2-) in THF-d 8 have been synthesized and studied by dynamic NMR spectroscopy. Rate constants for bond shift (k BS) in the neutral cyclooctatetraene (COT) rings of 1−4 and 1 2-−4 2- and for intramolecular charge (electron and cation) transfer (k CT) between the dianion and the neutral COT rings in 1 2-−4 2- have been determined. 13C NMR chemical shifts and AM1 π-charges as well as the values of k CT are interpreted on the basis of a stronger through-bond interaction between the COT rings in the order 1 2- ≫ 2 2- ≥ 4 2- > 3 2-. Similarly, k BS decreases in the order 1 2- ≫ 4 2- > 2 2- > 3 2- on going from 1−4 to the corresponding dianions. Analysis of the AM1 π-charge densities suggests that these differences are primarily due to a through-bond effect with an additional through-space contribution from the electric field of the dianion ring for bond shift in 4 2-.

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Synthetic routes to bridged dicyclooctatetraenes and alkynylcyclooctatetraenes

Cited by 18 publications

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Building with Cubane-1,4-diyl. Synthesis of Aryl-Substituted Cubanes, p-[n]Cubyls, and Cubane-Separated Bis(arenes)¹

Building with Cubane-1,4-diyl. Synthesis of Aryl-Substituted Cubanes, p-[n]Cubyls, and Cubane-Separated Bis(arenes)¹

Rational design of diarylethylene‐based polymeric semiconductors for high‐performance organic field‐effect transistors

Kinetics of Bond Shift and Charge Transfer in Dialkynylphenylene-Bridged Dicyclooctatetraenes and Their Dianions

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Synthetic routes to bridged dicyclooctatetraenes and alkynylcyclooctatetraenes

Cited by 18 publications

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Building with Cubane-1,4-diyl. Synthesis of Aryl-Substituted Cubanes, p-[n]Cubyls, and Cubane-Separated Bis(arenes)1

Building with Cubane-1,4-diyl. Synthesis of Aryl-Substituted Cubanes, p-[n]Cubyls, and Cubane-Separated Bis(arenes)1

Rational design of diarylethylene‐based polymeric semiconductors for high‐performance organic field‐effect transistors

Kinetics of Bond Shift and Charge Transfer in Dialkynylphenylene-Bridged Dicyclooctatetraenes and Their Dianions

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Building with Cubane-1,4-diyl. Synthesis of Aryl-Substituted Cubanes, p-[n]Cubyls, and Cubane-Separated Bis(arenes)¹

Building with Cubane-1,4-diyl. Synthesis of Aryl-Substituted Cubanes, p-[n]Cubyls, and Cubane-Separated Bis(arenes)¹