Exact helical polymer synthesis by a two-point-covalent-linking protocol between C2-chiral spirobifluorene and C2- or Cs-symmetric anthraquinone monomers

Yi, Zhaozhong; Okuda, Hitoshi; Koyama, Yasuhito; Seto, Ryota; Uchida, Satoshi; Sogawa, Hiromitsu; Kuwata, Shigeki; Takata, Toshikazu

doi:10.1039/c5cc02086g

Cited by 24 publications

(17 citation statements)

References 38 publications

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“…Takata et al developed a method to synthesize helical polymers based on rigid C -chial repeating units. [61] In 2015, they constructed a coil-shaped compound 82 and screw-shaped compound 84 (Scheme 28), with rigid structures, via reductive cyclization reactions. Surprisingly, the two polymers were highly soluble in water, since sulfonation might occur on the fluorene moieties.…”

Section: Rigid Polymersmentioning

confidence: 99%

Rigidly Fused Spiro‐Conjugated π‐Systems

Xia

Baumgarten

2020

ChemPlusChem

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Spiro‐fused π‐systems have gained considerable attention for their application as semiconductors in molecular electronics. Here, a synopsis regarding recent breakthroughs in ladderized spirobifluorenes and indeno‐spirobifluorenes, along with further spiro‐condensed heteroatomic hydrocarbons with donor‐acceptor moieties, is provided. Additionally, an extended range of rigid spirobifluorene polymers and specific doubly linked spiro‐systems with partial chiral character is discussed. The diverse applications of the aforementioned structures are thoroughly evaluated.

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Section: Rigid Polymersmentioning

confidence: 99%

Rigidly Fused Spiro‐Conjugated π‐Systems

Xia

Baumgarten

2020

ChemPlusChem

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“…[5c] Spiro-conjugated frameworks have been utilized as attractive and useful building blocks for optically-active spiro-bridged ladder-type oligomers [7] owing to the axially chiral spiro scaffold, thereby forming unique orthogonallyconjugated chiral architecture with intriguing circularly polarized luminescence (CPL). Chiral spirobifluorene units were also employed to construct optically active helical ladder-like polymers by Takata and co-workers, [8] but these structures were not fully characterized.…”

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confidence: 99%

Synthesis of Single‐Handed Helical Spiro‐Conjugated Ladder Polymers through Quantitative and Chemoselective Cyclizations**

2021

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We report the unprecedented synthesis of onehanded helical spiro-conjugated ladder polymers with welldefined primary and secondary structures, in which the spirolinked dibenzo [a,h]anthracene fluorophores are arranged in a one-handed twisting direction, through quantitative and chemoselective acid-promoted intramolecular cyclizations of random-coil precursor polymers composed of chiral 1,1'spirobiindane and achiral bis[2-(4-alkoxyphenyl)ethynyl]phenylene units. Intense circular dichroism (CD) and circularly polarized luminescence (CPL) were observed, whereas the precursor polymers exhibited negligible CD and CPL activities. The introduction of 2,6-dimethyl substituents on the 4alkoxyphenylethynyl pendants is of key importance for this simple, quantitative, and chemoselective cyclization. This strategy is applicable to the defect-free precise synthesis of other varieties of fully p-conjugated molecules and coplanar ladder polymers that have not been achieved before.

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“…Scheme 137 , Section 4.3 ). 64 Polycondensation of 137.1 with the anthraquinone spacer 36.1 efficiently gave the polymeric precursor 36.2 in 86% yield ( Scheme 36 ). A subsequent intramolecular cyclization reaction of 36.2 upon treatment with H 2 SO 4 quantitatively afforded a screw-shaped helical polymer 36.3 .…”

Section: Perylenoidsmentioning

confidence: 99%