Role of Second Halogen Atoms of Dihalobenzene in Controlling the Photoluminescence Properties of Single-Walled Carbon Nanotubes by Reductive Arylation

Yutaka Maeda; Atsushi Suwa; Kentaro Kawada; Pei Zhao; Masahiro Ehara; Yasuhiro Suzuki; Yui Iguchi; Yasunari Taki; Yui Konno; Michio Yamada; Hitoshi Kasai; Koji Kimoto; Koji Harano

doi:10.1021/acsnanoscienceau.5c00152

Journal article Role of Second Halogen Atoms of Dihalobenzene in Controlling the Photoluminescence Properties of Single-Walled Carbon Nanotubes by Reductive Arylation

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Yutaka Maeda, Atsushi Suwa, Kentaro Kawada, Pei Zhao, Masahiro Ehara, Yasuhiro Suzuki, Yui Iguchi, Yasunari Taki, Yui Konno, Michio Yamada, Hitoshi Kasai, Koji Kimoto, Koji Harano. Role of Second Halogen Atoms of Dihalobenzene in Controlling the Photoluminescence Properties of Single-Walled Carbon Nanotubes by Reductive Arylation. ACS Nanoscience Au. 2026, 6 (2), 270-280. https://doi.org/10.1021/acsnanoscienceau.5c00152

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The chemical functionalization of single-walled carbon nanotubes (SWCNTs) is effective for controlling their near-infrared (NIR) photoluminescence (PL) wavelength by locally modulating the band gap energy of the SWCNTs. The PL efficiency is dependent on the degree of functionalization. Herein, SWCNTs were reductively arylated using sodium naphthalenide and halo- and dihalobenzene derivatives to control their PL properties. (6,5) SWCNTs functionalized with iodobenzene exhibited two new PL peaks at 1100 and 1230 nm. In contrast, the arylated SWCNTs prepared using fluorobenzene and chlorobenzene exhibited a single new PL peak at 1100 nm. Furthermore, the arylated SWCNTs prepared using dihalobenzene derivatives exhibited a new PL peak at 1230 nm, which was dependent on the type and number of halogen atoms. The relative stabilities and transition energies of the model compounds for the arylated SWCNTs were estimated using theoretical calculations. These results suggest that their transition energies can be tuned by the binding configuration, and that the relative stability of the binding configuration varies depending on the addenda. The arylated SWCNTs were chirally separated, and an analysis of the optical properties of the separated SWCNT adducts revealed that this arylation reaction is effective for tuning the PL wavelength and intensity of (6,4), (7,3), (8,3), and (7,5) SWCNTs with different chiral indices in the NIR region. The addenda on the SWCNTs were successfully observed using transmittance electron microscopy by isolating the functionalized (6,5) SWCNTs and subsequent thermal treatment.

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Creative Commons BY-NC-ND Attribution-NonCommercial-NoDerivs 4.0 International

Keyword: single-walled carbon nanotubes, infrared, photoluminescence, functionalization, transmission electron microscopy

Date published: 2026-04-15

Publisher: American Chemical Society (ACS)

Journal:

ACS Nanoscience Au (ISSN: 26942496) vol. 6 issue. 2 p. 270-280

Funding:

Japan Society for the Promotion of Science JP17H02735
Japan Society for the Promotion of Science JP20H02210
Japan Society for the Promotion of Science JP20H02718
Japan Society for the Promotion of Science JP21H01759
Japan Society for the Promotion of Science JP22H05133
Japan Society for the Promotion of Science JP23H04874

Manuscript type: Publisher's version (Version of record)

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First published URL: https://doi.org/10.1021/acsnanoscienceau.5c00152

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Updated at: 2026-04-16 04:21:22 +0900

Published on MDR: 2026-04-16 16:26:11 +0900

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