Colorless Near-Infrared Absorbing Dyes Based on B-N Fused Donor-Acceptor-Donor π-Conjugated Molecules for Organic Phototransistors

Yokoyama, Soichi; Utsunomiya, Sakura; Seo, Takuji; Saeki, Akinori; Ie, Yutaka

doi:https://doi.org/10.1002/advs.202405656

Colorless Near-Infrared Absorbing Dyes Based on B-N Fused Donor-Acceptor-Donor π-Conjugated Molecules for Organic Phototransistors

Yokoyama, Soichi; Utsunomiya, Sakura; Seo, Takuji et al.

Advanced Science, 2024

アクセス数:23件（2025-03-17 08:25 集計）

固定URL: https://hdl.handle.net/11094/97612

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タイトル	Colorless Near-Infrared Absorbing Dyes Based on B-N Fused Donor-Acceptor-Donor π-Conjugated Molecules for Organic Phototransistors
著者	NRID 1000040811211 1000040811211 ORCID 0000-0001-6218-1159 0000-0001-6218-1159 researchmap permalink Soichi_Yokoyama Soichi_Yokoyama Scopus Author ID 57197721206 57197721206 著者名 Yokoyama, Soichi
	著者名 Utsunomiya, Sakura
	著者名 Seo, Takuji
	NRID 1000010362625 1000010362625 ORCID 0000-0001-7429-2200 0000-0001-7429-2200 researchmap permalink a-saeki a-saeki Scopus Author ID 7004268947 7004268947 著者名 Saeki, Akinori
	NRID 1000080362622 1000080362622 researchmap permalink read0105668 read0105668 Scopus Author ID 55930140700 55930140700 著者名 Ie, Yutaka
キーワード等	colorless characteristics
	electronic transitions
	NIR absorbing dyes
	organic phototransistors
	organic semiconductors
内容	Yokoyama S., Utsunomiya S., Seo T., et al. Colorless Near-Infrared Absorbing Dyes Based on B-N Fused Donor-Acceptor-Donor π-Conjugated Molecules for Organic Phototransistors. Advanced Science, (2024); https://doi.org/10.1002/advs.202405656.
抄録	The introduction of a colorless function to organic electronic devices allows responses to light in the near-infrared (NIR) region and is expected to broaden the applications of these devices. However, the development of a colorless NIR dye remains a challenge due to the lack of a rational molecular design for controlling electronic transitions. In this study, to suppress the π-π* transitions in the visible region, polycyclic donor-acceptor-donor π-conjugated molecules with boron bridges (Py-FNTz-B and IP-FNTz-B) are designed and synthesized, which contain pyrrole or indenopyrrole as donor units with fluorinated naphthobisthiadiazole (FNTz) as an acceptor unit. The pyrrole end-capped Py-FNTz-B shows an absorption band in the NIR region without distinct visible-light absorption, which has led to the establishment of colorless characteristics. The indenopyrrole end-capped IP-FNTz-B shows a narrow optical energy gap of 0.87 eV in films. Time-resolved microwave conductance and field-effect transistors demonstrate the semiconducting characteristics of these molecules, and Py-FNTz-B-based devices function as NIR phototransistors. Theoretical analyses indicate that the combination of a polyene-like electronic structure with orbital symmetry is important to obtain NIR wavelength-selective absorption. This study suggests that a molecular design based on electronic structures can be effective in the development of colorless NIR-absorbing dyes for organic electronics.
出版者	John Wiley and Sons Inc
収録物名	Advanced Science
刊行年月	2024-06-14
言語	英語
ハンドルURL	https://hdl.handle.net/11094/97612
eISSN	21983844
関連情報 (isIdenticalTo)	DOI (出版社版) https://doi.org/10.1002/advs.202405656
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	Advanced Science. 2024
DC.title	Colorless Near-Infrared Absorbing Dyes Based on B-N Fused Donor-Acceptor-Donor π-Conjugated Molecules for Organic Phototransistors
DC.creator	Yokoyama, Soichi
	Utsunomiya, Sakura
	Seo, Takuji
	Saeki, Akinori
	Ie, Yutaka
DC.publisher	John Wiley and Sons Inc
DC.language' scheme='DCTERMS.RFC1766	英語
DCTERMS.issued' scheme='DCTERMS.W3CDTF	2024-06-14
DC.identifier	https://doi.org/10.1002/advs.202405656
DC.subject	colorless characteristics
	electronic transitions
	NIR absorbing dyes
	organic phototransistors
	organic semiconductors
DC.description	Yokoyama S., Utsunomiya S., Seo T., et al. Colorless Near-Infrared Absorbing Dyes Based on B-N Fused Donor-Acceptor-Donor π-Conjugated Molecules for Organic Phototransistors. Advanced Science, (2024); https://doi.org/10.1002/advs.202405656.
DCTERMS.abstract	The introduction of a colorless function to organic electronic devices allows responses to light in the near-infrared (NIR) region and is expected to broaden the applications of these devices. However, the development of a colorless NIR dye remains a challenge due to the lack of a rational molecular design for controlling electronic transitions. In this study, to suppress the π-π* transitions in the visible region, polycyclic donor-acceptor-donor π-conjugated molecules with boron bridges (Py-FNTz-B and IP-FNTz-B) are designed and synthesized, which contain pyrrole or indenopyrrole as donor units with fluorinated naphthobisthiadiazole (FNTz) as an acceptor unit. The pyrrole end-capped Py-FNTz-B shows an absorption band in the NIR region without distinct visible-light absorption, which has led to the establishment of colorless characteristics. The indenopyrrole end-capped IP-FNTz-B shows a narrow optical energy gap of 0.87 eV in films. Time-resolved microwave conductance and field-effect transistors demonstrate the semiconducting characteristics of these molecules, and Py-FNTz-B-based devices function as NIR phototransistors. Theoretical analyses indicate that the combination of a polyene-like electronic structure with orbital symmetry is important to obtain NIR wavelength-selective absorption. This study suggests that a molecular design based on electronic structures can be effective in the development of colorless NIR-absorbing dyes for organic electronics.
DC.rights	This article is licensed under a Creative Commons Attribution 4.0 International License.
DC.format	97612
citation_title	Colorless Near-Infrared Absorbing Dyes Based on B-N Fused Donor-Acceptor-Donor π-Conjugated Molecules for Organic Phototransistors
citation_author	Yokoyama, Soichi
	Utsunomiya, Sakura
	Seo, Takuji
	Saeki, Akinori
	Ie, Yutaka
citation_publisher	John Wiley and Sons Inc
citation_language	英語
citation_date	2024-06-14
citation_journal_title	Advanced Science
citation_doi	https://doi.org/10.1002/advs.202405656
citation_public_url	https://hdl.handle.net/11094/97612

Colorless Near-Infrared Absorbing Dyes Based on B-N Fused Donor-Acceptor-Donor π-Conjugated Molecules for Organic Phototransistors

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