Article Well-Structured Narrow Near-Infrared Absorption Based on Nonaggregated Hexarylene-Bisimide toward a Colorless Dye

Shoko Yoshida ; Nozomi Kasakura ; Miho Hirakawa ; Hirofumi Morimoto ; Kyohei Matsuo ; Hironobu Hayashi SAMURAI ORCID ; Mitsuaki Yamauchi ORCID ; Ryutarou Kanamori ; Soji Shimizu ORCID ; Hiroko Yamada ORCID ; Naoki Aratani ORCID

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Shoko Yoshida, Nozomi Kasakura, Miho Hirakawa, Hirofumi Morimoto, Kyohei Matsuo, Hironobu Hayashi, Mitsuaki Yamauchi, Ryutarou Kanamori, Soji Shimizu, Hiroko Yamada, Naoki Aratani. Well-Structured Narrow Near-Infrared Absorption Based on Nonaggregated Hexarylene-Bisimide toward a Colorless Dye. The Journal of Organic Chemistry. 2025, 90 (44), 15489-15494. https://doi.org/10.1021/acs.joc.5c01320

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(abstract)

Extended π-conjugated systems are often insoluble, and their aggregation manner greatly affects their absorption spectra. This study produced a planar, soluble, and nonaggregated hexarylene-bisimide (HB) with appropriate substituents. The single-crystal X-ray structure of HB confirmed the planar molecular structure with small twist angles and the dimerization behavior of HB in the solid state. The concentration-dependent 1H NMR experiments in CDCl3 indicated that the association constant Kdimer is 4.6 × 103 M–1 at 298 K and ΔGdimer (298 K) = −20.8 kJ mol–1. The longest absorption of HB at the monomeric state exhibits a sharp and intense peak at 921 nm (ε = 230,000 M–1 cm–1, full width at half-maximum = 718 cm–1) in toluene. 75% of the absorption of HB above 400 nm appears in the near-infrared region, thus giving a practically colorless solution. Magnetic circular dichroism spectra of a series of oligorylene-bisimides reveal the predominant contribution of the linear polyene-like conjugation over the annulene-like conjugation for larger [n]oligorylene-bisimides.

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Keyword: dye, aromatic compound, single crystal, near-infrared absorbing, Magnetic circular dichroism

Date published: 2025-11-07

Publisher: American Chemical Society (ACS)

Journal:

  • The Journal of Organic Chemistry (ISSN: 00223263) vol. 90 issue. 44 p. 15489-15494

Funding:

  • Nara Institute of Science and Technology
  • Ministry of Education, Culture, Sports, Science and Technology JPMXP1225NR5003
  • Masuya Memorial Basic Research Foundation
  • Casio Science Promotion Foundation J41-23
  • Ministry of Education, Culture, Sports, Science and Technology JPMJPR21AC
  • Ministry of Education, Culture, Sports, Science and Technology JP20H05833
  • Ministry of Education, Culture, Sports, Science and Technology JP23K23332
  • Ministry of Education, Culture, Sports, Science and Technology JP23K26480
  • Ministry of Education, Culture, Sports, Science and Technology JP24K01576
  • Ministry of Education, Culture, Sports, Science and Technology JP25K01751

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

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First published URL: https://doi.org/10.1021/acs.joc.5c01320

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Updated at: 2025-12-10 12:30:10 +0900

Published on MDR: 2025-12-10 12:23:53 +0900

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