Near-infrared absorption of a benzothiophene-appended triphenylamine radical cation: A novel molecular design of NIR-II dye

Masafumi Yano; Yoshinori Inada; Yuki Hayashi; Misaki Nakai; Koichi Mitsudo; Yukiyasu Kashiwagi

doi:10.1016/j.dyepig.2021.109929

Near-infrared absorption of a benzothiophene-appended triphenylamine radical cation: A novel molecular design of NIR-II dye

Masafumi Yano, Yoshinori Inada, Yuki Hayashi, Misaki Nakai, Koichi Mitsudo, Yukiyasu Kashiwagi

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

Abstract

A triphenylamine with three benzothiophene rings was designed and successfully synthesized in 87% yield. The compound showed absorption at 386 nm and blue emission at around 442 nm, with a fluorescence quantum yield of 0.57. The compound showed high thermostability. The radical cation obtained by one-electron oxidation was stable in solution and showed a significant absorption in the NIR-II region (λ_max = 1213 nm). DFT calculations confirmed the experimental data.

Original language	English
Article number	109929
Journal	Dyes and Pigments
Volume	197
DOIs	https://doi.org/10.1016/j.dyepig.2021.109929
Publication status	Published - Jan 2022

Keywords

Benzothiophene
Near-infrared absorption
NIR-II dye
Stable radical cation
Triphenylamine

ASJC Scopus subject areas

Chemical Engineering(all)
Process Chemistry and Technology

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10.1016/j.dyepig.2021.109929

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title = "Near-infrared absorption of a benzothiophene-appended triphenylamine radical cation: A novel molecular design of NIR-II dye",

abstract = "A triphenylamine with three benzothiophene rings was designed and successfully synthesized in 87% yield. The compound showed absorption at 386 nm and blue emission at around 442 nm, with a fluorescence quantum yield of 0.57. The compound showed high thermostability. The radical cation obtained by one-electron oxidation was stable in solution and showed a significant absorption in the NIR-II region (λmax = 1213 nm). DFT calculations confirmed the experimental data.",

keywords = "Benzothiophene, Near-infrared absorption, NIR-II dye, Stable radical cation, Triphenylamine",

author = "Masafumi Yano and Yoshinori Inada and Yuki Hayashi and Misaki Nakai and Koichi Mitsudo and Yukiyasu Kashiwagi",

note = "Funding Information: The authors would like to thank Dr Hitoshi Ishida, Kansai University, for the measurements of UV?vis?NIR and spectra, and Dr Masashi Nakamura, Osaka Research Institute of Industrial Science and Technology, for the measurements of fluorescence quantum yield. Publisher Copyright: {\textcopyright} 2021 Elsevier Ltd",

year = "2022",

month = jan,

doi = "10.1016/j.dyepig.2021.109929",

language = "English",

volume = "197",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier BV",

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TY - JOUR

T1 - Near-infrared absorption of a benzothiophene-appended triphenylamine radical cation

T2 - A novel molecular design of NIR-II dye

AU - Yano, Masafumi

AU - Inada, Yoshinori

AU - Hayashi, Yuki

AU - Nakai, Misaki

AU - Mitsudo, Koichi

AU - Kashiwagi, Yukiyasu

N1 - Funding Information: The authors would like to thank Dr Hitoshi Ishida, Kansai University, for the measurements of UV?vis?NIR and spectra, and Dr Masashi Nakamura, Osaka Research Institute of Industrial Science and Technology, for the measurements of fluorescence quantum yield. Publisher Copyright: © 2021 Elsevier Ltd

PY - 2022/1

Y1 - 2022/1

N2 - A triphenylamine with three benzothiophene rings was designed and successfully synthesized in 87% yield. The compound showed absorption at 386 nm and blue emission at around 442 nm, with a fluorescence quantum yield of 0.57. The compound showed high thermostability. The radical cation obtained by one-electron oxidation was stable in solution and showed a significant absorption in the NIR-II region (λmax = 1213 nm). DFT calculations confirmed the experimental data.

AB - A triphenylamine with three benzothiophene rings was designed and successfully synthesized in 87% yield. The compound showed absorption at 386 nm and blue emission at around 442 nm, with a fluorescence quantum yield of 0.57. The compound showed high thermostability. The radical cation obtained by one-electron oxidation was stable in solution and showed a significant absorption in the NIR-II region (λmax = 1213 nm). DFT calculations confirmed the experimental data.

KW - Benzothiophene

KW - Near-infrared absorption

KW - NIR-II dye

KW - Stable radical cation

KW - Triphenylamine

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DO - 10.1016/j.dyepig.2021.109929

M3 - Article

AN - SCOPUS:85118875944

VL - 197

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

M1 - 109929

ER -

Near-infrared absorption of a benzothiophene-appended triphenylamine radical cation: A novel molecular design of NIR-II dye

Abstract

Keywords

ASJC Scopus subject areas

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