Acid Responsive Hydrogen-Bonded Organic Frameworks

Hisaki, Ichiro; Suzuki, Yuto; Gomez, Eduardo; Ji, Qin; Tohnai, Norimitsu; Nakamura, Takayoshi; Douhal, Abderrazzak

doi:https://doi.org/10.1021/jacs.8b12124

Acid Responsive Hydrogen-Bonded Organic Frameworks

Hisaki, Ichiro; Suzuki, Yuto; Gomez, Eduardo et al.

Journal of the American Chemical Society, 2019, 141(5), 2111-2121

アクセス数:665件（2025-07-18 10:43 集計）

固定URL: https://hdl.handle.net/11094/92728

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タイトル	Acid Responsive Hydrogen-Bonded Organic Frameworks
著者	NRID 1000090419466 1000090419466 ORCID 0000-0002-8170-5605 0000-0002-8170-5605 researchmap permalink Ichiro_Hisaki Ichiro_Hisaki Scopus Author ID 12801798700 12801798700 著者名 Hisaki, Ichiro
	著者名 Suzuki, Yuto
	著者名 Gomez, Eduardo
	著者名 Ji, Qin
	NRID 1000030346184 1000030346184 researchmap permalink read0089607 read0089607 Scopus Author ID 6701482198 6701482198 ORCID 0000-0001-7051-7599 0000-0001-7051-7599 著者名 Tohnai, Norimitsu
	NRID 1000060270790 1000060270790 著者名 Nakamura, Takayoshi
	著者名 Douhal, Abderrazzak
内容	Hisaki I., Suzuki Y., Gomez E., et al. Acid Responsive Hydrogen-Bonded Organic Frameworks. Journal of the American Chemical Society. 141(5), 2111-2121, (2019), 6 February 2019; © 2019 American Chemical Society. https://doi.org/10.1021/jacs.8b12124.
抄録	A porous hydrogen-bonded organic framework (HOF) responsive to acid was constructed from a hexaazatrinaphthylene derivative with carboxyphenyl groups (CPHATN). Precise structures of both 1,2,4-trichlorobenzene solvate [CPHATN-1(TCB)] and activated HOF with permanent porosity (CPHATN-1a) were successfully determined by single-crystalline X-ray diffraction analysis. Permanent porosity of CPHATN-1a was evaluated by gas sorption experiments at low temperature. CPHATN-1a also shows significant thermal stability up to 633 K. Its crystals exhibit a rich photochemistry thanks to intramolecular charge-transfer and interunit proton-transfer reactions. Femtosecond (fs) experiments on crystals demonstrate that these events occur in ≤200 fs and 1.2 ps, respectively. Moreover, single-crystal fluorescence microscopy reveals a shift of the emission spectra most probably as a result of defects and a high anisotropic behavior, reflecting an ordered crystalline structure with a preferential orientation of the molecular dipole moments. Remarkably, CPHATN-1a, as a result of the protonation of pyradyl nitrogen atoms embedded in its π-conjugated core, shows reversible vapor acid-induced color changes from yellow to reddish-brown, which can be also followed by an ON/OFF of its emission. To the best of our knowledge, this is the first HOF that exhibits acid-responsive color changes. The present work provides new findings for developing stimuli responsive HOFs.
出版者	American Chemical Societyservice
収録物名	Journal of the American Chemical Society
巻(号)	141(5)
ページ	2111-2121
刊行年月	2019-02-06
言語	英語
ハンドルURL	https://hdl.handle.net/11094/92728
PISSN	00027863
eISSN	15205126
関連情報 (isVersionOf)	DOI (出版社版) https://doi.org/10.1021/jacs.8b12124
アクセス権	open access
権利情報	© 2019 American Chemical Society
出版タイプ	Accepted Manuscript
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. 2019, 141(5), p. 2111-2121
DC.title	Acid Responsive Hydrogen-Bonded Organic Frameworks
DC.creator	Hisaki, Ichiro
	Suzuki, Yuto
	Gomez, Eduardo
	Ji, Qin
	Tohnai, Norimitsu
	Nakamura, Takayoshi
	Douhal, Abderrazzak
DC.publisher	American Chemical Societyservice
DC.language' scheme='DCTERMS.RFC1766	英語
DC.type' scheme='DCTERMS.DCMIType	text
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2019-02-06
DC.identifier	https://doi.org/10.1021/jacs.8b12124
DC.description	Hisaki I., Suzuki Y., Gomez E., et al. Acid Responsive Hydrogen-Bonded Organic Frameworks. Journal of the American Chemical Society. 141(5), 2111-2121, (2019), 6 February 2019; © 2019 American Chemical Society. https://doi.org/10.1021/jacs.8b12124.
DCTERMS.abstract	A porous hydrogen-bonded organic framework (HOF) responsive to acid was constructed from a hexaazatrinaphthylene derivative with carboxyphenyl groups (CPHATN). Precise structures of both 1,2,4-trichlorobenzene solvate [CPHATN-1(TCB)] and activated HOF with permanent porosity (CPHATN-1a) were successfully determined by single-crystalline X-ray diffraction analysis. Permanent porosity of CPHATN-1a was evaluated by gas sorption experiments at low temperature. CPHATN-1a also shows significant thermal stability up to 633 K. Its crystals exhibit a rich photochemistry thanks to intramolecular charge-transfer and interunit proton-transfer reactions. Femtosecond (fs) experiments on crystals demonstrate that these events occur in ≤200 fs and 1.2 ps, respectively. Moreover, single-crystal fluorescence microscopy reveals a shift of the emission spectra most probably as a result of defects and a high anisotropic behavior, reflecting an ordered crystalline structure with a preferential orientation of the molecular dipole moments. Remarkably, CPHATN-1a, as a result of the protonation of pyradyl nitrogen atoms embedded in its π-conjugated core, shows reversible vapor acid-induced color changes from yellow to reddish-brown, which can be also followed by an ON/OFF of its emission. To the best of our knowledge, this is the first HOF that exhibits acid-responsive color changes. The present work provides new findings for developing stimuli responsive HOFs.
DC.rights	© 2019 American Chemical Society
DC.format	92728
citation_title	Acid Responsive Hydrogen-Bonded Organic Frameworks
citation_author	Hisaki, Ichiro
	Suzuki, Yuto
	Gomez, Eduardo
	Ji, Qin
	Tohnai, Norimitsu
	Nakamura, Takayoshi
	Douhal, Abderrazzak
citation_publisher	American Chemical Societyservice
citation_language	英語
citation_date	2019-02-06
citation_journal_title	Journal of the American Chemical Society
citation_volume	141
citation_issue	5
citation_firstpage	2111
citation_lastpage	2121
citation_doi	https://doi.org/10.1021/jacs.8b12124
citation_public_url	https://hdl.handle.net/11094/92728

Acid Responsive Hydrogen-Bonded Organic Frameworks

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