Isoacenofuran: A novel quinoidal building block for efficient access to high-ordered polyacene derivatives

Kei Kitamura; Ryoji Kudo; Haruki Sugiyama; Hidehiro Uekusa; Toshiyuki Hamura

doi:10.1039/d0cc06620f

Isoacenofuran: A novel quinoidal building block for efficient access to high-ordered polyacene derivatives

Kei Kitamura, Ryoji Kudo, Haruki Sugiyama, Hidehiro Uekusa, Toshiyuki Hamura

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

Abstract

Herein, a simple and practical method for generating isoacenofuran, a new π-extended quinoidal building block, was developed. A three-step protocol involving double nucleophilic additions of alkynyllithiums to acene-2,3-dicarbaldehyde, mono-oxidation, and acid-promoted cyclization enables the generation of the target molecule, which is trapped by a dienophile to produce highly condensed acenequinones. Further transformations by double nucleophilic additions of alkynyllithium to hexacenequinone, followed by reductive aromatization, produce tetraalkynylhexacenes with a remarkably higher stability than that of the previously reported substituted hexacenes.

Original language	English
Pages (from-to)	14988-14991
Number of pages	4
Journal	Chemical Communications
Volume	56
Issue number	95
DOIs	https://doi.org/10.1039/d0cc06620f
Publication status	Published - 2020 Dec 11
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d0cc06620f

Cite this

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title = "Isoacenofuran: A novel quinoidal building block for efficient access to high-ordered polyacene derivatives",

abstract = "Herein, a simple and practical method for generating isoacenofuran, a new π-extended quinoidal building block, was developed. A three-step protocol involving double nucleophilic additions of alkynyllithiums to acene-2,3-dicarbaldehyde, mono-oxidation, and acid-promoted cyclization enables the generation of the target molecule, which is trapped by a dienophile to produce highly condensed acenequinones. Further transformations by double nucleophilic additions of alkynyllithium to hexacenequinone, followed by reductive aromatization, produce tetraalkynylhexacenes with a remarkably higher stability than that of the previously reported substituted hexacenes.",

author = "Kei Kitamura and Ryoji Kudo and Haruki Sugiyama and Hidehiro Uekusa and Toshiyuki Hamura",

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language = "English",

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T2 - A novel quinoidal building block for efficient access to high-ordered polyacene derivatives

AU - Kitamura, Kei

AU - Kudo, Ryoji

AU - Sugiyama, Haruki

AU - Uekusa, Hidehiro

AU - Hamura, Toshiyuki

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Number JP15H05840 in Middle Molecular Strategy and JST ACT-C Grant Number JPMJCR12YY, Japan. Publisher Copyright: © The Royal Society of Chemistry.

PY - 2020/12/11

Y1 - 2020/12/11

N2 - Herein, a simple and practical method for generating isoacenofuran, a new π-extended quinoidal building block, was developed. A three-step protocol involving double nucleophilic additions of alkynyllithiums to acene-2,3-dicarbaldehyde, mono-oxidation, and acid-promoted cyclization enables the generation of the target molecule, which is trapped by a dienophile to produce highly condensed acenequinones. Further transformations by double nucleophilic additions of alkynyllithium to hexacenequinone, followed by reductive aromatization, produce tetraalkynylhexacenes with a remarkably higher stability than that of the previously reported substituted hexacenes.

AB - Herein, a simple and practical method for generating isoacenofuran, a new π-extended quinoidal building block, was developed. A three-step protocol involving double nucleophilic additions of alkynyllithiums to acene-2,3-dicarbaldehyde, mono-oxidation, and acid-promoted cyclization enables the generation of the target molecule, which is trapped by a dienophile to produce highly condensed acenequinones. Further transformations by double nucleophilic additions of alkynyllithium to hexacenequinone, followed by reductive aromatization, produce tetraalkynylhexacenes with a remarkably higher stability than that of the previously reported substituted hexacenes.

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Isoacenofuran: A novel quinoidal building block for efficient access to high-ordered polyacene derivatives

Abstract

ASJC Scopus subject areas

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