Synthesis of a Black Dye with Absorption Capabilities across the Visible-to-Near-Infrared Region: A MO-Mixing Approach via Heterometal Coordination of Expanded Porphyrinoid

Yue Wang; Hiroto Kai; Masatoshi Ishida; Sabapathi Gokulnath; Shigeki Mori; Tomotaka Murayama; Atsuya Muranaka; Masanobu Uchiyama; Yuhsuke Yasutake; Susumu Fukatsu; Yusuke Notsuka; Yoshihisa Yamaoka; Mamiko Hanafusa; Michito Yoshizawa; Gakhyun Kim; Dongho Kim; Hiroyuki Furuta

doi:10.1021/jacs.0c01824

Synthesis of a Black Dye with Absorption Capabilities across the Visible-to-Near-Infrared Region: A MO-Mixing Approach via Heterometal Coordination of Expanded Porphyrinoid

Yue Wang, Hiroto Kai, Masatoshi Ishida, Sabapathi Gokulnath, Shigeki Mori, Tomotaka Murayama, Atsuya Muranaka, Masanobu Uchiyama, Yuhsuke Yasutake, Susumu Fukatsu, Yusuke Notsuka, Yoshihisa Yamaoka, Mamiko Hanafusa, Michito Yoshizawa, Gakhyun Kim, Dongho Kim, Hiroyuki Furuta

Department of Chemistry

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28 Citations (Scopus)

Abstract

An expanded metalloporphyrin-based "black dye" Au-Pd oxohexaphyrin (AuPd-1) with absorption capabilities across the visible-to-near-infrared (NIR) range was synthesized. This black dye, AuPd-1, possessed efficient light-harvesting and photostable capabilities, which were indicative of superior photothermal (PT) conversion abilities. Encapsulation of AuPd-1 with a micellar nanocapsule resulted in a compound that demonstrated intense photoacoustic (PA) properties in the NIR region in water. This finding indicated how metal (d)-ligand (π) molecular orbital interactions in metalloporphyrins could aid in the design of visible-to-NIR light-harvesting black dyes for PT and PA applications.

Original language	English
Pages (from-to)	6807-6813
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	142
Issue number	14
DOIs	https://doi.org/10.1021/jacs.0c01824
Publication status	Published - 2020 Apr 8

Bibliographical note

Funding Information:
The present work at Kyushu University and Tokyo Institute of Technology (Yokohama) was supported by JSPS KAKENHI Grant Numbers (JP19H04586, JP19H04566, and JP19K05439). Funding from the Tokuyama Research Foundation is gratefully acknowledged. HOKUSAI (RIKEN) provided the computer resources for some parts of DFT calculations. The work at Yonsei University was supported by Strategic Research (NRF2016R1E1A1A01943379) through the National Research Foundation of Korea (NRF) funded by the Ministry of Science. Finally, we acknowledge Prof. T. Yasuda, Prof. D. Kawaguchi, and Prof. K. Tanaka at Kyushu University for helping us for simulated solar light irradiation experiment.

Funding Information:
The present work at Kyushu University and Tokyo Institute of Technology (Yokohama) was supported by JSPS KAKENHI Grant Numbers (JP19H04586, JP19H04566, and JP19K05439). Funding from the Tokuyama Research Foundation is gratefully acknowledged. HOKUSAI (RIKEN) provided the computer resources for some parts of DFT calculations. The work at Yonsei University was supported by Strategic Research (NRF2016R1E1A1A01943379) through the National Research Foundation of Korea (NRF) funded by the Ministry of Science. Finally, we acknowledge Prof. T. Yasuda Prof. D. Kawaguchi, and Prof. K. Tanaka at Kyushu University for helping us for simulated solar light irradiation experiment.

Publisher Copyright:
© 2020 American Chemical Society.

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.0c01824

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Wang, Y., Kai, H., Ishida, M., Gokulnath, S., Mori, S., Murayama, T., Muranaka, A., Uchiyama, M., Yasutake, Y., Fukatsu, S., Notsuka, Y., Yamaoka, Y., Hanafusa, M., Yoshizawa, M., Kim, G., Kim, D., & Furuta, H. (2020). Synthesis of a Black Dye with Absorption Capabilities across the Visible-to-Near-Infrared Region: A MO-Mixing Approach via Heterometal Coordination of Expanded Porphyrinoid. Journal of the American Chemical Society, 142(14), 6807-6813. https://doi.org/10.1021/jacs.0c01824

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title = "Synthesis of a Black Dye with Absorption Capabilities across the Visible-to-Near-Infrared Region: A MO-Mixing Approach via Heterometal Coordination of Expanded Porphyrinoid",

abstract = "An expanded metalloporphyrin-based {"}black dye{"} Au-Pd oxohexaphyrin (AuPd-1) with absorption capabilities across the visible-to-near-infrared (NIR) range was synthesized. This black dye, AuPd-1, possessed efficient light-harvesting and photostable capabilities, which were indicative of superior photothermal (PT) conversion abilities. Encapsulation of AuPd-1 with a micellar nanocapsule resulted in a compound that demonstrated intense photoacoustic (PA) properties in the NIR region in water. This finding indicated how metal (d)-ligand (π) molecular orbital interactions in metalloporphyrins could aid in the design of visible-to-NIR light-harvesting black dyes for PT and PA applications.",

author = "Yue Wang and Hiroto Kai and Masatoshi Ishida and Sabapathi Gokulnath and Shigeki Mori and Tomotaka Murayama and Atsuya Muranaka and Masanobu Uchiyama and Yuhsuke Yasutake and Susumu Fukatsu and Yusuke Notsuka and Yoshihisa Yamaoka and Mamiko Hanafusa and Michito Yoshizawa and Gakhyun Kim and Dongho Kim and Hiroyuki Furuta",

note = "Funding Information: The present work at Kyushu University and Tokyo Institute of Technology (Yokohama) was supported by JSPS KAKENHI Grant Numbers (JP19H04586, JP19H04566, and JP19K05439). Funding from the Tokuyama Research Foundation is gratefully acknowledged. HOKUSAI (RIKEN) provided the computer resources for some parts of DFT calculations. The work at Yonsei University was supported by Strategic Research (NRF2016R1E1A1A01943379) through the National Research Foundation of Korea (NRF) funded by the Ministry of Science. Finally, we acknowledge Prof. T. Yasuda, Prof. D. Kawaguchi, and Prof. K. Tanaka at Kyushu University for helping us for simulated solar light irradiation experiment. Funding Information: The present work at Kyushu University and Tokyo Institute of Technology (Yokohama) was supported by JSPS KAKENHI Grant Numbers (JP19H04586, JP19H04566, and JP19K05439). Funding from the Tokuyama Research Foundation is gratefully acknowledged. HOKUSAI (RIKEN) provided the computer resources for some parts of DFT calculations. The work at Yonsei University was supported by Strategic Research (NRF2016R1E1A1A01943379) through the National Research Foundation of Korea (NRF) funded by the Ministry of Science. Finally, we acknowledge Prof. T. Yasuda Prof. D. Kawaguchi, and Prof. K. Tanaka at Kyushu University for helping us for simulated solar light irradiation experiment. Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = apr,

day = "8",

doi = "10.1021/jacs.0c01824",

language = "English",

volume = "142",

pages = "6807--6813",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

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Wang, Y, Kai, H, Ishida, M, Gokulnath, S, Mori, S, Murayama, T, Muranaka, A, Uchiyama, M, Yasutake, Y, Fukatsu, S, Notsuka, Y, Yamaoka, Y, Hanafusa, M, Yoshizawa, M, Kim, G, Kim, D & Furuta, H 2020, 'Synthesis of a Black Dye with Absorption Capabilities across the Visible-to-Near-Infrared Region: A MO-Mixing Approach via Heterometal Coordination of Expanded Porphyrinoid', Journal of the American Chemical Society, vol. 142, no. 14, pp. 6807-6813. https://doi.org/10.1021/jacs.0c01824

Synthesis of a Black Dye with Absorption Capabilities across the Visible-to-Near-Infrared Region: A MO-Mixing Approach via Heterometal Coordination of Expanded Porphyrinoid. / Wang, Yue; Kai, Hiroto; Ishida, Masatoshi et al.
In: Journal of the American Chemical Society, Vol. 142, No. 14, 08.04.2020, p. 6807-6813.

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

TY - JOUR

T1 - Synthesis of a Black Dye with Absorption Capabilities across the Visible-to-Near-Infrared Region

T2 - A MO-Mixing Approach via Heterometal Coordination of Expanded Porphyrinoid

AU - Wang, Yue

AU - Kai, Hiroto

AU - Ishida, Masatoshi

AU - Gokulnath, Sabapathi

AU - Mori, Shigeki

AU - Murayama, Tomotaka

AU - Muranaka, Atsuya

AU - Uchiyama, Masanobu

AU - Yasutake, Yuhsuke

AU - Fukatsu, Susumu

AU - Notsuka, Yusuke

AU - Yamaoka, Yoshihisa

AU - Hanafusa, Mamiko

AU - Yoshizawa, Michito

AU - Kim, Gakhyun

AU - Kim, Dongho

AU - Furuta, Hiroyuki

N1 - Funding Information: The present work at Kyushu University and Tokyo Institute of Technology (Yokohama) was supported by JSPS KAKENHI Grant Numbers (JP19H04586, JP19H04566, and JP19K05439). Funding from the Tokuyama Research Foundation is gratefully acknowledged. HOKUSAI (RIKEN) provided the computer resources for some parts of DFT calculations. The work at Yonsei University was supported by Strategic Research (NRF2016R1E1A1A01943379) through the National Research Foundation of Korea (NRF) funded by the Ministry of Science. Finally, we acknowledge Prof. T. Yasuda, Prof. D. Kawaguchi, and Prof. K. Tanaka at Kyushu University for helping us for simulated solar light irradiation experiment. Funding Information: The present work at Kyushu University and Tokyo Institute of Technology (Yokohama) was supported by JSPS KAKENHI Grant Numbers (JP19H04586, JP19H04566, and JP19K05439). Funding from the Tokuyama Research Foundation is gratefully acknowledged. HOKUSAI (RIKEN) provided the computer resources for some parts of DFT calculations. The work at Yonsei University was supported by Strategic Research (NRF2016R1E1A1A01943379) through the National Research Foundation of Korea (NRF) funded by the Ministry of Science. Finally, we acknowledge Prof. T. Yasuda Prof. D. Kawaguchi, and Prof. K. Tanaka at Kyushu University for helping us for simulated solar light irradiation experiment. Publisher Copyright: © 2020 American Chemical Society.

PY - 2020/4/8

Y1 - 2020/4/8

N2 - An expanded metalloporphyrin-based "black dye" Au-Pd oxohexaphyrin (AuPd-1) with absorption capabilities across the visible-to-near-infrared (NIR) range was synthesized. This black dye, AuPd-1, possessed efficient light-harvesting and photostable capabilities, which were indicative of superior photothermal (PT) conversion abilities. Encapsulation of AuPd-1 with a micellar nanocapsule resulted in a compound that demonstrated intense photoacoustic (PA) properties in the NIR region in water. This finding indicated how metal (d)-ligand (π) molecular orbital interactions in metalloporphyrins could aid in the design of visible-to-NIR light-harvesting black dyes for PT and PA applications.

AB - An expanded metalloporphyrin-based "black dye" Au-Pd oxohexaphyrin (AuPd-1) with absorption capabilities across the visible-to-near-infrared (NIR) range was synthesized. This black dye, AuPd-1, possessed efficient light-harvesting and photostable capabilities, which were indicative of superior photothermal (PT) conversion abilities. Encapsulation of AuPd-1 with a micellar nanocapsule resulted in a compound that demonstrated intense photoacoustic (PA) properties in the NIR region in water. This finding indicated how metal (d)-ligand (π) molecular orbital interactions in metalloporphyrins could aid in the design of visible-to-NIR light-harvesting black dyes for PT and PA applications.

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SN - 0002-7863

VL - 142

SP - 6807

EP - 6813

JO - Journal of the American Chemical Society

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IS - 14

ER -

Synthesis of a Black Dye with Absorption Capabilities across the Visible-to-Near-Infrared Region: A MO-Mixing Approach via Heterometal Coordination of Expanded Porphyrinoid

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