A Diradical Approach towards BODIPY-Based Dyes with Intense Near-Infrared Absorption around λ=1100 nm

Yong Ni, Sangsu Lee, Minjung Son, Naoki Aratani, Masatoshi Ishida, Animesh Samanta, Hiroko Yamada, Young Tae Chang, Hiroyuki Furuta, Dongho Kim, Jishan Wu

Research output: Contribution to journalArticle

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Abstract

A diradical approach to obtain stable organic dyes with intense absorption around λ=1100 nm is reported. The para- and meta-quinodimethane-bridged BODIPY dimers BD-1 and BD-2 were synthesized and were found to have a small amount of diradical character. These molecules exhibited very intense absorption at λ=1088 nm (ɛ=6.65×105 M−1 cm−1) and 1136 nm (ɛ=6.44×105 M−1 cm−1), respectively, together with large two-photon-absorption cross-sections. Structural isomerization induced little variation in their diradical character but distinctive differences in their physical properties. Moreover, the compounds showed a selective fluorescence turn-on response in the presence of the hydroxyl radical but not with other reactive oxygen species.
Original languageEnglish
Pages (from-to)2815-2819
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number8
DOIs
Publication statusPublished - 2016 Feb 18

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Infrared absorption
Isomerization
Hydroxyl Radical
Dimers
Reactive Oxygen Species
Coloring Agents
Photons
Dyes
Physical properties
Fluorescence
Molecules
Oxygen
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene

Cite this

Ni, Yong ; Lee, Sangsu ; Son, Minjung ; Aratani, Naoki ; Ishida, Masatoshi ; Samanta, Animesh ; Yamada, Hiroko ; Chang, Young Tae ; Furuta, Hiroyuki ; Kim, Dongho ; Wu, Jishan. / A Diradical Approach towards BODIPY-Based Dyes with Intense Near-Infrared Absorption around λ=1100 nm. In: Angewandte Chemie - International Edition. 2016 ; Vol. 55, No. 8. pp. 2815-2819.
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abstract = "A diradical approach to obtain stable organic dyes with intense absorption around λ=1100 nm is reported. The para- and meta-quinodimethane-bridged BODIPY dimers BD-1 and BD-2 were synthesized and were found to have a small amount of diradical character. These molecules exhibited very intense absorption at λ=1088 nm (ɛ=6.65×105 M−1 cm−1) and 1136 nm (ɛ=6.44×105 M−1 cm−1), respectively, together with large two-photon-absorption cross-sections. Structural isomerization induced little variation in their diradical character but distinctive differences in their physical properties. Moreover, the compounds showed a selective fluorescence turn-on response in the presence of the hydroxyl radical but not with other reactive oxygen species.",
author = "Yong Ni and Sangsu Lee and Minjung Son and Naoki Aratani and Masatoshi Ishida and Animesh Samanta and Hiroko Yamada and Chang, {Young Tae} and Hiroyuki Furuta and Dongho Kim and Jishan Wu",
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Ni, Y, Lee, S, Son, M, Aratani, N, Ishida, M, Samanta, A, Yamada, H, Chang, YT, Furuta, H, Kim, D & Wu, J 2016, 'A Diradical Approach towards BODIPY-Based Dyes with Intense Near-Infrared Absorption around λ=1100 nm', Angewandte Chemie - International Edition, vol. 55, no. 8, pp. 2815-2819. https://doi.org/10.1002/anie.201511151

A Diradical Approach towards BODIPY-Based Dyes with Intense Near-Infrared Absorption around λ=1100 nm. / Ni, Yong; Lee, Sangsu; Son, Minjung; Aratani, Naoki; Ishida, Masatoshi; Samanta, Animesh; Yamada, Hiroko; Chang, Young Tae; Furuta, Hiroyuki; Kim, Dongho; Wu, Jishan.

In: Angewandte Chemie - International Edition, Vol. 55, No. 8, 18.02.2016, p. 2815-2819.

Research output: Contribution to journalArticle

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AU - Ishida, Masatoshi

AU - Samanta, Animesh

AU - Yamada, Hiroko

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AU - Wu, Jishan

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