Biased Bowl-Direction of Monofluorosumanene in the Solid State

Yakiyama, Yumi; Li, Minghong; Zhou, Dongyi et al.

Journal of the American Chemical Society, 2024, 146(8), 5224-5231

Number of Access:892（2025-07-31 17:05 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/94882

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Title
Biased Bowl-Direction of Monofluorosumanene in the Solid State
Creator
NRID
1000060636819 1000060636819
ORCID
0000-0003-4278-2015 0000-0003-4278-2015
researchmap permalink
yumiyakiyama yumiyakiyama
Scopus Author ID
57195377416 57195377416
CreatorName
Yakiyama, Yumi
CreatorName
Li, Minghong
CreatorName
Zhou, Dongyi
CreatorName
Abe, Tsuyoshi
CreatorName
Sato, Chisato
CreatorName
Sambe, Kohei
NRID
1000060271631 1000060271631
CreatorName
Akutagawa, Tomoyuki
CreatorName
Matsumura, Teppei
NRID
1000020281107 1000020281107
ORCID
0000-0001-7176-441X 0000-0001-7176-441X
researchmap permalink
nbyk_MTBYS nbyk_MTBYS
Scopus Author ID
7003410578 7003410578
CreatorName
Matubayasi, Nobuyuki
NRID
1000000262147 1000000262147
ORCID
0000-0001-5783-4151 0000-0001-5783-4151
researchmap permalink
read0184917 read0184917
Scopus Author ID
7402869823 7402869823
CreatorName
Sakurai, Hidehiro
Description
Yakiyama Y., Li M., Zhou D., et al. Biased Bowl-Direction of Monofluorosumanene in the Solid State. Journal of the American Chemical Society 146, 5224 (2024); https://doi.org/10.1021/jacs.3c11311.
Abstract
A new curved π-conjugated molecule 1-fluorosumanene (1) was designed and synthesized that possesses one fluorine atom on the benzylic carbon of sumanene. This compound can exhibit bowl inversion in solution, leading to the formation of two diastereomers, 1endo and 1exo, with different dipole moments. Experimental and theoretical investigation revealed an energetical relationship among 1exo, 1endo, and solvent to realize the various endo:exo ratios in the single crystals of 1 depending on the crystallization solvent. Significantly, the molecular dynamics (MD) simulations revealed that 1exo positively worked for the elongation of the stacking structure and the final endo:exo ratio was affected by the relative stability difference between 1endo and 1exo derived by solvation. Such an arrangeable endo:exo ratio of 1 realized the preparation of unique materials showing a different dielectric response from the same molecule 1 just by changing the crystallization solvent.
Publisher
American Chemical Society
Source Title
Journal of the American Chemical Society
Volume (Issue)
146(8)
Page
5224-5231
Date of Issued
2024-02-28
Language
English
Handle URL
https://hdl.handle.net/11094/94882
PISSN
00027863
eISSN
15205126
Relation.isIdenticalTo
DOI (Publisher Version)
https://doi.org/10.1021/jacs.3c11311
Access Rights
open access
CopyRight
© 2024 The Authors. Published by American Chemical Society.
This article is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
oaire:version
Version of Record
Category
学術雑誌論文 Journal Article