Impact of helical elongation of symmetric oxa[n]helicenes on their structural, photophysical, and chiroptical characteristics

Salem, Mohamed S.H.; Sharma, Rubal; Suzuki, Seika; Imai, Yoshitane; Arisawa, Mitsuhiro; Takizawa, Shinobu

doi:https://doi.org/10.1002/chir.23673

Impact of helical elongation of symmetric oxa[n]helicenes on their structural, photophysical, and chiroptical characteristics

Salem, Mohamed S.H.; Sharma, Rubal; Suzuki, Seika et al.

Chirality, 2024, 36(5), e23673

アクセス数:791件（2025-08-14 16:44 集計）

固定URL: https://hdl.handle.net/11094/97140

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タイトル	Impact of helical elongation of symmetric oxa[n]helicenes on their structural, photophysical, and chiroptical characteristics
著者	著者名 Salem, Mohamed S.H.
	著者名 Sharma, Rubal
	著者名 Suzuki, Seika
	NRID 1000080388496 1000080388496 著者名 Imai, Yoshitane
	NRID 1000040312962 1000040312962 ORCID 0000-0002-7937-670X 0000-0002-7937-670X researchmap permalink read0054866 read0054866 Scopus Author ID 7102922041 7102922041 著者名 Arisawa, Mitsuhiro
	NRID 1000050324851 1000050324851 ORCID 0000-0002-9668-1888 0000-0002-9668-1888 researchmap permalink read0068650 read0068650 Scopus Author ID 7102334067 7102334067 著者名 Takizawa, Shinobu
キーワード等	chiroptical
	circular dichroism
	circularly polarized luminescence
	crystal analysis
	enantiomerization barrier
	helical elongation
	helicene
	time-dependent DFT
内容	Salem M.S.H., Sharma R., Suzuki S., et al. Impact of helical elongation of symmetric oxa[n]helicenes on their structural, photophysical, and chiroptical characteristics. Chirality 36, e23673 (2024); https://doi.org/10.1002/chir.23673.
抄録	The adjustment of the main helical scaffold in helicenes is a fundamental strategy for modulating their optical features, thereby enhancing their potential for diverse applications. This work explores the influence of helical elongation (n = 5–9) on the structural, photophysical, and chiroptical features of symmetric oxa[n]helicenes. Crystal structure analyses revealed structural variations with helical extension, impacting torsion angles, helical pitch, and packing arrangements. Through theoretical investigations using density functional theory (DFT) calculations, the impact of helical extension on aromaticity, planarity distortion, and heightened chiral stability were discussed. Photophysical features were studied through spectrophotometric analysis, with insights gained through time-dependent DFT (TD-DFT) calculations. Following optical resolution via chiral high-performance liquid chromatography (HPLC), the chiroptical properties of both enantiomers of oxa[7]helicene and oxa[9]helicene were investigated. A slight variation in the main helical scaffold of oxa[n]helicenes from [7] to [9] induced an approximately three-fold increase in dissymmetry factors with the biggest values of\|glum\| of oxa[9]helicene (2.2 × 10−3) compared to\|glum\|of oxa[7]helicene (0.8 × 10−3), findings discussed and supported by TD-DFT calculations.
出版者	John Wiley and Sons Inc
収録物名	Chirality
巻(号)	36(5)
ページ	e23673
刊行年月	2024-05-02
言語	英語
ハンドルURL	https://hdl.handle.net/11094/97140
PISSN	08990042
eISSN	1520636X
関連情報 (isIdenticalTo)	DOI (出版社版) https://doi.org/10.1002/chir.23673
アクセス権	open access
権利情報	This article is licensed under a Creative Commons Attribution 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
DCTERMS.bibliographicCitation	Chirality. 2024, 36(5), p. e23673
DC.title	Impact of helical elongation of symmetric oxa[n]helicenes on their structural, photophysical, and chiroptical characteristics
DC.creator	Salem, Mohamed S.H.
	Sharma, Rubal
	Suzuki, Seika
	Imai, Yoshitane
	Arisawa, Mitsuhiro
	Takizawa, Shinobu
DC.publisher	John Wiley and Sons Inc
DC.language' scheme='DCTERMS.RFC1766	英語
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2024-05-02
DC.identifier	https://doi.org/10.1002/chir.23673
DC.subject	chiroptical
	circular dichroism
	circularly polarized luminescence
	crystal analysis
	enantiomerization barrier
	helical elongation
	helicene
	time-dependent DFT
DC.description	Salem M.S.H., Sharma R., Suzuki S., et al. Impact of helical elongation of symmetric oxa[n]helicenes on their structural, photophysical, and chiroptical characteristics. Chirality 36, e23673 (2024); https://doi.org/10.1002/chir.23673.
DCTERMS.abstract	The adjustment of the main helical scaffold in helicenes is a fundamental strategy for modulating their optical features, thereby enhancing their potential for diverse applications. This work explores the influence of helical elongation (n = 5–9) on the structural, photophysical, and chiroptical features of symmetric oxa[n]helicenes. Crystal structure analyses revealed structural variations with helical extension, impacting torsion angles, helical pitch, and packing arrangements. Through theoretical investigations using density functional theory (DFT) calculations, the impact of helical extension on aromaticity, planarity distortion, and heightened chiral stability were discussed. Photophysical features were studied through spectrophotometric analysis, with insights gained through time-dependent DFT (TD-DFT) calculations. Following optical resolution via chiral high-performance liquid chromatography (HPLC), the chiroptical properties of both enantiomers of oxa[7]helicene and oxa[9]helicene were investigated. A slight variation in the main helical scaffold of oxa[n]helicenes from [7] to [9] induced an approximately three-fold increase in dissymmetry factors with the biggest values of\|glum\| of oxa[9]helicene (2.2 × 10−3) compared to\|glum\|of oxa[7]helicene (0.8 × 10−3), findings discussed and supported by TD-DFT calculations.
DC.rights	This article is licensed under a Creative Commons Attribution 4.0 International License.
DC.format	97140
citation_title	Impact of helical elongation of symmetric oxa[n]helicenes on their structural, photophysical, and chiroptical characteristics
citation_author	Salem, Mohamed S.H.
	Sharma, Rubal
	Suzuki, Seika
	Imai, Yoshitane
	Arisawa, Mitsuhiro
	Takizawa, Shinobu
citation_publisher	John Wiley and Sons Inc
citation_language	英語
citation_date	2024-05-02
citation_journal_title	Chirality
citation_volume	36
citation_issue	5
citation_firstpage	e23673
citation_doi	https://doi.org/10.1002/chir.23673
citation_public_url	https://hdl.handle.net/11094/97140

Impact of helical elongation of symmetric oxa[n]helicenes on their structural, photophysical, and chiroptical characteristics

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