Construction of Multiple Five‐Membered Rings in Dibenzo[<i>g</i>,<i>p</i>]chrysene Core for the Synthesis of a Nona‐Cycle Buckybowl

Abstract C 60 ‐fragmentary bowl‐shaped molecules, commonly referred to as “buckybowls”, are provocative compounds, and their inviting functions based on the non‐planar π‐conjugation are expected. Yet, achieving synthesis of some kinds of the curved structure remaining challenging. Herein we report skeletal construction of a nona‐cyclic buckybowl that is synthetically unachievable heretofore, namely, 3,10‐dihydroindeno[7,1,2‐ pqr ]‐ as ‐indaceno[3,2,1,8,7‐ defghi ]chrysene. The key to success was solution‐compatible process in which a multiple substituted dibenzo[ g , p ]chrysene is amenable to threefold formation of five‐membered rings at its periphery. The resulting scheme here, coupled with the gently curved scaffold, offers a new insight into the solution‐phase synthesis of curved and twisted polyarenes.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2024-09-02
DOI
https://doi.org/10.1002/ejoc.202400881
Primary Topic
Morinda citrifolia extract uses
Type
article
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article

Construction of Multiple Five‐Membered Rings in Dibenzo[g,p]chrysene Core for the Synthesis of a Nona‐Cycle Buckybowl

Yousuke Yamaoka, Tomoya Imai, Naruhiro Yoshida, Toru Amaya et al.
European Journal of Organic Chemistry
Morinda citrifolia extract uses
article

Construction of Multiple Five‐Membered Rings in Dibenzo[g,p]chrysene Core for the Synthesis of a Nona‐Cycle Buckybowl

Yousuke Yamaoka, Tomoya Imai, Naruhiro Yoshida, Toru Amaya, Tetsuo Iwasawa
article en

Abstract

Abstract C 60 ‐fragmentary bowl‐shaped molecules, commonly referred to as “buckybowls”, are provocative compounds, and their inviting functions based on the non‐planar π‐conjugation are expected. Yet, achieving synthesis of some kinds of the curved structure remaining challenging. Herein we report skeletal construction of a nona‐cyclic buckybowl that is synthetically unachievable heretofore, namely, 3,10‐dihydroindeno[7,1,2‐ pqr ]‐ as ‐indaceno[3,2,1,8,7‐ defghi ]chrysene. The key to success was solution‐compatible process in which a multiple substituted dibenzo[ g , p ]chrysene is amenable to threefold formation of five‐membered rings at its periphery. The resulting scheme here, coupled with the gently curved scaffold, offers a new insight into the solution‐phase synthesis of curved and twisted polyarenes.

European Journal of Organic ChemistryVol. 27(47)
Ryukoku University (JP), Hyogo University of Health Sciences (JP), Nagoya City University (JP), Hyogo University (JP)
Openalex Percentile: Top 72%
Morinda citrifolia extract uses
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