Post-Modification of Pyrrolopyrrole Aza-BODIPY toward High Near-Infrared Fluorescence Brightness

Yitong Wang; Shigeki Mori; Hajime Nakanotani; Chihaya Adachi; Soji Shimizu

doi:10.1021/acs.orglett.3c00848

Post-Modification of Pyrrolopyrrole Aza-BODIPY toward High Near-Infrared Fluorescence Brightness

Yitong Wang, Shigeki Mori, Hajime Nakanotani, Chihaya Adachi, Soji Shimizu

Functional Materials Chemistry

Research output: Contribution to journal › Article › peer-review

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Abstract

Pyrrolopyrrole aza-BODIPYs (PPABs), dimeric aza-BODIPY analogues, exhibit intense absorption and fluorescence in the visible and near-infrared (NIR) regions. Here, we developed a facile postmodification by palladium-catalyzed coupling reactions to synthesize a series of donor-acceptor-donor (D-A-D) PPABs. Despite the possible fluorescence quenching dictated by the energy-gap low, D-A-D PPABs exhibit high-fluorescence brightness in the NIR region, implying their potential use as a bright NIR emitter.

Original language	English
Pages (from-to)	3040-3044
Number of pages	5
Journal	Organic letters
Volume	25
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.3c00848
Publication status	Published - May 5 2023

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.3c00848

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title = "Post-Modification of Pyrrolopyrrole Aza-BODIPY toward High Near-Infrared Fluorescence Brightness",

abstract = "Pyrrolopyrrole aza-BODIPYs (PPABs), dimeric aza-BODIPY analogues, exhibit intense absorption and fluorescence in the visible and near-infrared (NIR) regions. Here, we developed a facile postmodification by palladium-catalyzed coupling reactions to synthesize a series of donor-acceptor-donor (D-A-D) PPABs. Despite the possible fluorescence quenching dictated by the energy-gap low, D-A-D PPABs exhibit high-fluorescence brightness in the NIR region, implying their potential use as a bright NIR emitter.",

author = "Yitong Wang and Shigeki Mori and Hajime Nakanotani and Chihaya Adachi and Soji Shimizu",

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AU - Wang, Yitong

AU - Mori, Shigeki

AU - Nakanotani, Hajime

AU - Adachi, Chihaya

AU - Shimizu, Soji

N1 - Funding Information: This work was supported by Grants-in-Aid from JSPS (Nos. JP22H02064 and JP19H02703) and Naohiko Fukuoka Memorial Foundation. Publisher Copyright: © 2023 American Chemical Society.

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N2 - Pyrrolopyrrole aza-BODIPYs (PPABs), dimeric aza-BODIPY analogues, exhibit intense absorption and fluorescence in the visible and near-infrared (NIR) regions. Here, we developed a facile postmodification by palladium-catalyzed coupling reactions to synthesize a series of donor-acceptor-donor (D-A-D) PPABs. Despite the possible fluorescence quenching dictated by the energy-gap low, D-A-D PPABs exhibit high-fluorescence brightness in the NIR region, implying their potential use as a bright NIR emitter.

AB - Pyrrolopyrrole aza-BODIPYs (PPABs), dimeric aza-BODIPY analogues, exhibit intense absorption and fluorescence in the visible and near-infrared (NIR) regions. Here, we developed a facile postmodification by palladium-catalyzed coupling reactions to synthesize a series of donor-acceptor-donor (D-A-D) PPABs. Despite the possible fluorescence quenching dictated by the energy-gap low, D-A-D PPABs exhibit high-fluorescence brightness in the NIR region, implying their potential use as a bright NIR emitter.

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Post-Modification of Pyrrolopyrrole Aza-BODIPY toward High Near-Infrared Fluorescence Brightness

Abstract

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