Chemistry of Anthracene−Acetylene Oligomers XXVII. Iterative Synthesis, Structures, and Properties of Anthracene−Diacetylene Cyclic Oligomers with 10‐Mesitylanthracene‐1,8‐diyl Units

Toyota, Shinji; Yoshikawa, Manami; Saibara, Toyoaki; Yokoyama, Yuya; Komori, Takashi; Iwanaga, Takeshi

doi:10.1002/cplu.201800433

Cited by 5 publications

(3 citation statements)

References 37 publications

(38 reference statements)

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“…The synthetic routes toward anthracene-based macrocycles 1 and 2 are depicted in Scheme 1. The key building block 1,8-diborate-10-mesitylanthracene (4) was synthesized from 1,8-dichloro-10-mesitylanthracene (3) 43 through the palladium-catalyzed Miyaura borylation reaction with bis (pinacolato)diboron in 42% yield. Subsequently, the selective Suzuki coupling of compound 4 with 1-bromo-4-iodobenzene or 1-bromo-3-iodobenzene afforded compounds 5 and 6 in the yield of 45% and 73%, respectively.…”

Section: Resultsmentioning

confidence: 99%

Phenyl-Linked Anthracene-Based Macrocycles with Geometrically Tunable Optical Properties

et al. 2020

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Anthracene has been widely explored because of its intrinsic photophysical and photochemical properties. Here, two novel anthracene-based macrocycles (1 and 2) were designed and synthesized with para- and meta-phenylene spacers. X-ray crystallographic analysis demonstrates that compound 1 with para-phenylene spacers adopts a nearly planar structure, while compound 2 with meta-phenylene spacers displays a V-shaped geometry. The photophysical properties of the resultant macrocycles, which are structural isomers, are well studied using photoluminescence spectra and time-resolved absorption spectra, which are further corroborated by density functional theory calculations. The optical properties of these two novel macrocycles can be finely tuned via their geometries.

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Section: Resultsmentioning

confidence: 99%

Phenyl-Linked Anthracene-Based Macrocycles with Geometrically Tunable Optical Properties

et al. 2020

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“…Toyota and co‐workers reported 1,8‐anthryleneethynylene‐containing macrocycles . The intramolecular Sonogashira–Hagihara coupling followed by Eglinton coupling afforded monoyne‐ and diyne‐containing macrocycles 184 and 185 , respectively (Figure b).…”

Section: Angle‐strained Alkyne‐containing π‐Conjugated Macrocyclesmentioning

confidence: 99%

“…To yota and co-workers reported 1,8-anthryleneethynylenecontaining macrocycles. [297][298][299][300][301][302][303] The intramolecular Sonogashira-Hagihara coupling followed by Eglinton coupling afforded monoyne-and diyne-containing macrocycles 184 and 185,r espectively (Figure 59 b). Although 184 and 186 show interesting dynamic behaviors such as swinging and pedaling, these Review macrocycles are strain free (Figure 60).…”

Section: Thiophene Spacersmentioning

confidence: 99%

π‐Conjugated Macrocycles Bearing Angle‐Strained Alkynes

Miki

Ohe

2019

Chemistry A European J

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Angle‐strained alkyne‐containing π‐conjugated macrocycles are attractive compounds both in functional materials chemistry and biochemistry. Their interesting reactivity as well as photophysical and supramolecular properties have been revealed in the past three decades. This review highlights the recent advances in angle‐strained alkyne‐containing π‐conjugated macrocycles, especially their synthetic methods, the bond angles of alkynes (∠sp at C≡C−C), and their functions. The theoretical and experimental research on cyclo[n]carbons and para‐cyclophynes consisting of ethynylenes and para‐phenylenes are mainly summarized. Related macrocycles bearing other linkers, such as ortho‐phenylenes, meta‐phenylenes, heteroaromatics, biphenyls, extended aromatics, are also overviewed. Bond angles of strained alkynes in π‐conjugated macrocycles, which are generable, detectable, and isolable, are summarized at the end of this review.

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Multiple Fused Anthracenes as Helical Polycyclic Aromatic Hydrocarbon Motif for Chiroptical Performance Enhancement

Fujise

Tsurumaki

Fukuhara

et al. 2020

Chemistry An Asian Journal

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Polycyclic aromatic hydrocarbons consisting of three fused anthracene units were designed as new π‐conjugated compounds having helical structures. These expanded helicenes were synthesized by Pt‐catalyzed cycloisomerization of the corresponding ethynyl‐substituted precursors. The nonplanar and helical structure was confirmed by X‐ray analysis and DFT calculations, and the barrier to helical inversion was estimated to be 34 kJ mol−1. The enantiomers of the diphenyl derivative were successfully resolved by chiral HPLC. Enantiopure samples showed good chiroptical performance in the CD (|Δϵ| 1380 L mol−1cm−1) and CPL (|glum| 0.013) spectra, and these values were considerably large for simple organic molecules. The unique chiroptical properties are discussed on the basis of the molecular structure and the electronic state with the aid of time‐dependent DFT calculations.

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Chemistry of Anthracene−Acetylene Oligomers XXVII. Iterative Synthesis, Structures, and Properties of Anthracene−Diacetylene Cyclic Oligomers with 10‐Mesitylanthracene‐1,8‐diyl Units

Cited by 5 publications

References 37 publications

Phenyl-Linked Anthracene-Based Macrocycles with Geometrically Tunable Optical Properties

Phenyl-Linked Anthracene-Based Macrocycles with Geometrically Tunable Optical Properties

π‐Conjugated Macrocycles Bearing Angle‐Strained Alkynes

Multiple Fused Anthracenes as Helical Polycyclic Aromatic Hydrocarbon Motif for Chiroptical Performance Enhancement

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