Biased Bowl-Direction of Monofluorosumanene in the Solid State

Yakiyama, Yumi; Li, Minghong; Zhou, Dongyi; Abe, Tsuyoshi; Sato, Chisato; Sambe, Kohei; Akutagawa, Tomoyuki; Matsumura, Teppei; Matubayasi, Nobuyuki; Sakurai, Hidehiro

doi:https://doi.org/10.1021/jacs.3c11311

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

アクセス数:41件（2025-04-04 23:44 集計）

固定URL: https://hdl.handle.net/11094/94882

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タイトル	Biased Bowl-Direction of Monofluorosumanene in the Solid State
著者	NRID 1000060636819 1000060636819 ORCID 0000-0003-4278-2015 0000-0003-4278-2015 researchmap permalink yumiyakiyama yumiyakiyama Scopus Author ID 57195377416 57195377416 著者名 Yakiyama, Yumi
	著者名 Li, Minghong
	著者名 Zhou, Dongyi
	著者名 Abe, Tsuyoshi
	著者名 Sato, Chisato
	著者名 Sambe, Kohei
	NRID 1000060271631 1000060271631 著者名 Akutagawa, Tomoyuki
	著者名 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 著者名 Matubayasi, Nobuyuki
	NRID 1000000262147 1000000262147 ORCID 0000-0001-5783-4151 0000-0001-5783-4151 researchmap permalink read0184917 read0184917 Scopus Author ID 7402869823 7402869823 著者名 Sakurai, Hidehiro
内容	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.
抄録	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.
出版者	American Chemical Society
収録物名	Journal of the American Chemical Society
巻(号)	146(8)
ページ	5224-5231
刊行年月	2024-02-28
言語	英語
ハンドルURL	https://hdl.handle.net/11094/94882
PISSN	00027863
eISSN	15205126
関連情報 (isIdenticalTo)	DOI (出版社版) https://doi.org/10.1021/jacs.3c11311
アクセス権	open access
権利情報	© 2024 The Authors. Published by American Chemical Society.
権利情報	This article is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
出版タイプ	Version of Record
カテゴリ	学術雑誌論文 Journal Article

資源タイプ	学術雑誌論文
ローカル資源タイプ	学術雑誌論文
DCMI資源タイプ	text
DCTERMS.bibliographicCitation	Journal of the American Chemical Society. 2024, 146(8), p. 5224-5231
DC.title	Biased Bowl-Direction of Monofluorosumanene in the Solid State
DC.creator	Yakiyama, Yumi
	Li, Minghong
	Zhou, Dongyi
	Abe, Tsuyoshi
	Sato, Chisato
	Sambe, Kohei
	Akutagawa, Tomoyuki
	Matsumura, Teppei
	Matubayasi, Nobuyuki
	Sakurai, Hidehiro
DC.publisher	American Chemical Society
DC.language' scheme='DCTERMS.RFC1766	英語
DC.type' scheme='DCTERMS.DCMIType	text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2024-02-28
DC.identifier	https://doi.org/10.1021/jacs.3c11311
DC.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.
DCTERMS.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.
DC.rights	© 2024 The Authors. Published by American Chemical Society.
DC.rights	This article is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
DC.format	94882
citation_title	Biased Bowl-Direction of Monofluorosumanene in the Solid State
citation_author	Yakiyama, Yumi
	Li, Minghong
	Zhou, Dongyi
	Abe, Tsuyoshi
	Sato, Chisato
	Sambe, Kohei
	Akutagawa, Tomoyuki
	Matsumura, Teppei
	Matubayasi, Nobuyuki
	Sakurai, Hidehiro
citation_publisher	American Chemical Society
citation_language	英語
citation_date	2024-02-28
citation_journal_title	Journal of the American Chemical Society
citation_volume	146
citation_issue	8
citation_firstpage	5224
citation_lastpage	5231
citation_doi	https://doi.org/10.1021/jacs.3c11311
citation_public_url	https://hdl.handle.net/11094/94882

Biased Bowl-Direction of Monofluorosumanene in the Solid State

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