Bent π‐Conjugated Systems Composed of Three‐Dimensional Benzoannulenes

Nishiuchi, Tomohiko; Iyoda, Masahiko

doi:10.1002/tcr.201402079

Cited by 29 publications

(26 citation statements)

References 141 publications

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“…1 ) 47 48 . The photoresponsive framework is composed of rigid anthracene wings and a flexible joint of cyclooctatetraene 49 50 51 . This hybrid design of rigidity and flexibility confers two important characteristics on the material.…”

Section: Resultsmentioning

confidence: 99%

Light-melt adhesive based on dynamic carbon frameworks in a columnar liquid-crystal phase

et al. 2016

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Liquid crystal (LC) provides a suitable platform to exploit structural motions of molecules in a condensed phase. Amplification of the structural changes enables a variety of technologies not only in LC displays but also in other applications. Until very recently, however, a practical use of LCs for removable adhesives has not been explored, although a spontaneous disorganization of LC materials can be easily triggered by light-induced isomerization of photoactive components. The difficulty of such application derives from the requirements for simultaneous implementation of sufficient bonding strength and its rapid disappearance by photoirradiation. Here we report a dynamic molecular LC material that meets these requirements. Columnar-stacked V-shaped carbon frameworks display sufficient bonding strength even during heating conditions, while its bonding ability is immediately lost by a light-induced self-melting function. The light-melt adhesive is reusable and its fluorescence colour reversibly changes during the cycle, visualizing the bonding/nonbonding phases of the adhesive.

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Section: Resultsmentioning

confidence: 99%

Light-melt adhesive based on dynamic carbon frameworks in a columnar liquid-crystal phase

et al. 2016

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“…41 However, a Corey-Winter reaction of the diol afforded a complex mixture of products (Scheme 7). 41 However, a Corey-Winter reaction of the diol afforded a complex mixture of products (Scheme 7).…”

Section: View Article Onlinementioning

confidence: 99%

Multifunctional π-expanded oligothiophene macrocycles

2015

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This tutorial review summarizes recent progress in the design, synthesis, and multifunctional properties of fully conjugated macrocyclic π-systems. We focus on the π-expanded oligothiophene macrocycles after a short survey of macrocyclic conjugated loops and belts such as [n]cycloparaphenylenes, cyclic[n]para-phenylacetylenes, [4]cyclo-2,8-crysenylenes, and cyclo[n]thiophenes. Fully conjugated π-expanded oligothiophene macrocycles possess shape-persistent but sometimes pliable π-frames, and the electronic and optoelectronic properties of the macrocycles largely depend on the π-systems inserted into the oligothiophene macrocycles. Among them, the π-expanded oligothiophene macrocycle composed of 2,5-thienylenes, ethynylenes, and vinylenes is one of the most widely applicable macrocycles for constructing multifunctional π-systems. These π-expanded oligothiophene macrocycles from small to very large ring sizes can be prepared via a short step procedure, and their various solid state structures can be determined by X-ray analysis. Since these macrocycles have inner and outer domains, specific information concerning structural, electronic, and optical properties is expected. Furthermore, π-expanded oligothiophene macrocycles with alkyl substituents exhibit various morphologies depending on nanophase separation of molecules, and a morphological change is observed for the molecular switch.

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“…Thep reparation of aconjugated belt from aflat precursor has been intensively pursued by the groups of Scott [9] as well as Iyoda, who detected the anticipated cyclophenacene 7 by LD-TOFmass spectrometry. [10,11] Itami and co-workers have now achieved the preparation, isolation, and full characterization of an aromatic nanobelt (Scheme 1). Thesynthesis is based on an iterative application of Wittig reactions to construct the brominated all-Z-configured phenylethenyl macrocycle 13.T he final aromatization was realized by an ickel-mediated reductive ring closure, which delivered the final nanobelt 14 in 1% yield.…”

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confidence: 99%