TY - JOUR
T1 - Isoacenofuran
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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U2 - 10.1039/d0cc06620f
DO - 10.1039/d0cc06620f
M3 - Article
C2 - 33179656
AN - SCOPUS:85097571204
SN - 1359-7345
VL - 56
SP - 14988
EP - 14991
JO - Chemical Communications
JF - Chemical Communications
IS - 95
ER -