Metal‐Bridging Cyclic Bilatriene Analogue Affords Stable π‐Radicaloid Dyes with Near‐Infrared II Absorption
Open accessAbstract
Stable neutral metal radicaloid complexes have been synthesized from a modified tetrapyrrolic pigment, bilatriene, with iridium(I) and rhodium(I) cyclooctadiene (COD) synthons. The bilatriene skeleton contains α‐linked conjugated pyrrole units, whereas an N‐confused analogue used in this work possesses β‐linked pyrrole moieties at the terminal, demonstrating a unique metal binding capability. Unprecedentedly, the metal‐COD cations are accommodated at the outer nitrogen sites, which induced the formation of open‐shell metal‐radicaloid species. The resulting compounds are highly stable under ambient conditions and demonstrated facile redox conversion to afford the corresponding cation and anion species. Furthermore, the radicaloid complexes showed a distinct second near‐infrared absorption (NIR‐II) capability extending up to 1500 nm along with high photostability. These features emphasized that the complexes can be potential NIR‐II light‐responsible photothermal and photoacoustic imaging contrast agents based on the metal‐radicaloid dye platform.
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Metal complexes are promising photofunctional materials due to superior photostability, large Stokes shifts, and high emission quantum yields compared to organic chromophores.
“Metal complexes are promising photofunctional materials due to their superior photostability, large Stokes shifts, and high emission quantum yields compared to organic chromophores”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [199]
The Conclusions (page unavailable) describe the studied metal complexes as promising light-responsive materials with high photostability. Results and Discussion (page unavailable) reports greater photostability than indocyanine green, but calls for minimal fluorescence quantum yields in the intended photoacoustic application. The paper does not support the claimed large Stokes shifts, high emission quantum yields, or a general comparison with organic chromophores. (LLM, conf=0.88)
Experimental — accuracy not yet measuredBiomedical application of metal complexes is hindered by a reliance on high-energy, short-wavelength excitation, leading to phototoxicity and poor tissue penetration.
“Nevertheless, their biomedical application is hindered by a reliance on high-energy, short-wavelength excitation, which leads to phototoxicity and poor tissue penetration.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [199]
The Introduction (page not provided) says NIR-II light permits higher maximum exposures and less tissue scattering than NIR-I light, and links NIR-II imaging to deeper tissue penetration. It does not say metal complexes generally rely on high-energy, short-wavelength excitation or that such excitation causes phototoxicity; the metal complexes studied absorb in the NIR-II range. (LLM, conf=0.82)
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- Authors
- Ghosh, A., Mori, S., Ide, Y., Song, J. T., Yamaoka, Y., Ishihara, T., Ikeue, T., Furuta, H., & Ishida, M.
- Affiliations
- Tokyo Metropolitan University (JP)
- Ehime University (JP)
- Hokkaido University (JP)
- Kyushu University (JP)
- Komatsu University (JP)
- Shimane University (JP)
- Corresponding author
- Ishida, Masatoshi
- ORCID
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2024-12-17
- Volume
- 64
- Issue
- 6
- Pages
- e202418751-e202418751
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- PMC
- PMC11795725
- OpenAlex
- W4405236207
- Cited by
- 14
- References
- 54
- Citations by year
- 2026: 9 · 2025: 5
- FWCI
- 1.37
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Angewandte Chemie International Edition (publishedVersion, cc-by-nc-nd)
- PubMed Central (publishedVersion, cc-by-nc-nd)
- PubMed (publishedVersion)
- Funders
- Japan Society for the Promotion of Science London (JP20H00406, JP22K19937)
- Japan Science and Technology Agency (JPMJPR2103)
- Izumi Science and Technology Foundation
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Porphyrin and Phthalocyanine Chemistry
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Properties of Aromatic Compounds
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Keywords
- iridium(I) complexes, rhodium(I) complexes, redox conversion, photostability
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