Sulphur‐Embedded Hydrocarbon Belts: Synthesis, Structure and Redox Chemistry of Cyclothianthrenes

Wang, Shenghua; Yuan, Jun; Xie, Junqiu; Lu, Zonghuan; Jiang, Long; Mu, Yingxiao; Huo, Yanping; Tsuchido, Yoshitaka; Zhu, Kelong

doi:10.1002/anie.202104054

Cited by 51 publications

(40 citation statements)

References 61 publications

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“…On the other hand, they possess the inherent chirality of the macrocyclic figure-eight and both ( P , P )- and ( M , M )- enantiomers could be isolated by chiral high performance liquid chromatography (HPLC). It is also worthy of note that recently two double-stranded, half-twisted Möbius stripes were reported by Tanaka and Zhu et al Particularly, the latter successfully resolved the racemic isomers.…”

mentioning

confidence: 76%

Synthesis and Chiral Resolution of Twisted Carbon Nanobelts

et al. 2021

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Twisted carbon nanobelts could display persistent chirality, which is desirable for material applications, but their synthesis is very challenging. Herein, we report the successful synthesis and chiral resolution of such a kind of molecules (1-H and 1) with a figure-eight configuration. 1-H was synthesized first by macrocyclization through Suzuki coupling reaction followed by benzannulation via Bi(OTf)3-mediated cyclization reaction of vinyl ether. Oxidative dehydrogenation of 1-H gave the fully π-conjugated 1. Their twisted structures were confirmed by X-ray crystallographic analysis and calculations, and they can be resolved by chiral high-performance liquid chromatography. The isolated enantiomers showed persistent chiroptical properties according to the circular dichroism measurements, with moderate |g abs| values (0.0016 for 1-H and 0.005–0.007 for 1). Their photophysical properties were also briefly studied.

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confidence: 76%

Synthesis and Chiral Resolution of Twisted Carbon Nanobelts

et al. 2021

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“…131 Macrocycles 144-147 were produced with high fidelity by using a Pummerer-type fragmentation to construct the thianthrene rings after macrocycle formation. 131 Although macrocycles 144-146 adopt the expected tubular shape, compound 147, with nine thianthrene units, adopts a Möbius conformation, as observed by 1 H NMR spectroscopy. 131 The synthesis of such structures was enabled by the non-planar geometry of the thianthrene heterocycle, which significantly reduces the strain of the resulting macrocycle, as compared to carbon-based analogues.…”

Section: Review Synthesismentioning

confidence: 99%

The Properties, Synthesis, and Materials Applications of 1,4-Dithiins and Thianthrenes

Swager¹,

Etkind²

2022

Synthesis

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Abstract1,4-Dithiin and its dibenzo-analogue, thianthrene, represent a class of non-aromatic, sulfur-rich heterocycles. Their unique properties, stemming from both their non-planar structures and reversible one- and two-electron oxidations, serve as primary motivators for their use in the development of new materials. The applications of 1,4-dithiins and thianthrenes are rich and diverse, having been used for energy storage and harvesting, and the synthesis of phosphorescent compounds and porous polymers, among other uses. This review offers first an overview of the properties of 1,4-dithiin and thianthrene. Next, we describe enabling synthetic methodology to access 1,4-dithiins and thianthrenes with various substitution patterns. Lastly, the utility of 1,4-dithiin and thianthrene in the construction and design of new materials is detailed using select literature examples.1 Introduction2 Properties of 1,4-Dithiins and Thianthrenes3 Synthesis of 1,4-Dithiins and Thianthrenes3.1 Synthesis of 1,4-Dithiins3.2 Synthesis of Thianthrenes4 Application of 1,4-Dithiins and Thianthrenes in Materials4.1 Thianthrene-Containing Polymers4.2 Thianthrene in Redox-Active Materials4.3 Thianthrenes and 1,4-Dithiins in Supramolecular Chemistry and Self-Assembly4.4 Thianthrenes in Phosphorescent Materials4.5 Thianthrenes with Other Interesting Photophysical Properties4.6 Thianthrenes in the Synthesis of Non-natural Products5 Conclusion

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“…Inspired by this thinking, Zhu et al recently demonstrated the synthesis of sulphur-embedded nanobelts with thianthrene moieties (Scheme 1). 13 In their initial design strategy, the introduction of thianthrene moieties would lead to dynamic nanobelts with not only reduced strain energies that originate from the bent and foldable structures of thianthrene units but also switchable complexation behaviors that originate from the redox tunable conformations of thianthrene moieties. Interestingly, in this study, the successful synthesis of a novel molecular Möbius strip was achieved.…”

Section: Nonconjugated Molecular Möbius Stripsmentioning

confidence: 99%