Constructing Stable and Wavelength‐Extended Heptamethine Cyanines via Donor Ectopic Substitution for NIR‐IIa/b Bioimaging
Abstract
Organic NIR‐II dyes, particularly cyanine fluorophores, offer high molar extinction coefficients, biocompatibility, and structural tunability and are popular for noninvasive, high‐resolution, and ‐contrast in vivo imaging. However, achieving stable, long‐wavelength, and large Stokes shift NIR‐II cyanine suitable for NIR‐IIa/IIb bioimaging is still a formidable challenge. Herein, we introduce a novel strategy that extends the emission wavelength by the enhanced Highest occupied molecular orbital (HOMO)–Lowest occupied molecular orbital (LUMO) separation through simple donor ectopic substitution at the terminal structure of NIR‐II cyanine. Compared to the original NIR‐II cyanine Flav7, these novel dyes (NIR‐ACs) exhibited a significant emission redshift and larger Stokes shift, with the maximum emission wavelength exceeding 1300 nm (NIR‐IIa) and a tail emission exceeding 1500 nm (NIR‐IIb). Notably, they also demonstrate excellent stability and deeper tissue imaging ability in vivo imaging. Finally, through surface modification of nanoparticles, NIR‐ACs nanoparticles (NPs) have successfully achieved high‐contrast tumor and bone‐targeted detecting as well as multicolor imaging, providing robust tools for in vivo diagnostics and biomedical research.
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NIR-ACs maximum emission extended beyond 1300 nm, with the spectral tail reaching above 1500 nm.
“Their maximum emission extended beyond 1300 nm, with the spectral tail reaching above 1500 nm.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [104]
Zhang et al. engineered NIR-ACs via simple donor ectopic substitution at the terminal structures of NIR-II cyanine.
“Zhang et al.104 engineered a series of novel dyes (NIR-ACs) via simple donor ectopic substitution at the terminal structures of NIR-II cyanine.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [104]
Compared to Flav7, NIR-ACs exhibited markedly red-shifted emission of 87-263 nm, substantially larger Stokes shifts of greater than 42 nm up to 112 nm, and favorable fluorescence brightness.
“Compared to the original NIR-II cyanine Flav7, these NIR-ACs exhibited markedly red-shifted emission (red-shifts of 87–263 nm), substantially larger Stokes shifts ( > 42 nm, up to 112 nm), and favorable fluorescence brightness.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [104]
Zhang et al. developed the novel heptamethine cyanine dye NIR-AC4 through donor ectopic substitution at the terminal structure of the NIR-II cyanine scaffold.
“Soon afterward, Zhang et al. developed the novel heptamethine cyanine dye (NIR-AC4) through donor ectopic substitution at the terminal structure of NIR-II cyanine scaffold (Fig. 14c)104.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [104]
Biotin-modified and alendronate-functionalized NIR-AC4 NPs exhibited enhanced affinity for tumor and bone tissues, respectively.
“Biotin-modified and alendronate-functionalized NIR-AC4 NPs exhibited enhanced affinity for tumor and bone tissues, respectively.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [104]
NIR-AC4 AaNPs yielded an SBR of 14.32, facilitating differentiation between spinous processes and vertebral bodies for precise osteoporosis detection in murine models.
“Similarly, NIR-AC4 AaNPs yielded an SBR of 14.32, facilitating differentiation between spinous processes and vertebral bodies with enhanced structural integrity for precise osteoporosis detection in murine models.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [104]
NIR-AC4 has stable NIR-II emission at 1206 nm and a fluorescence quantum yield of 0.063%.
“Due to its stable NIR-II emission (1206 nm) and fluorescence quantum yield (QY = 0.063%), NIR-AC4 generated strong fluorescence signals in cerebral and tumor blood vessels.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [104]
At 24 h post injection, NIR-AC4 Bio NPs attained a TNR of 15, affording high contrast NIR-IIb imaging for precise tumor resection and boundary delineation.
“At 24 h post injection, NIR-AC4 Bio NPs attained a TNR of 15, affording high contrast NIR-IIb imaging for precise tumor resection and boundary delineation.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [104]
NIR-AC4 generated strong fluorescence signals in cerebral and tumor blood vessels.
“Due to its stable NIR-II emission (1206 nm) and fluorescence quantum yield (QY = 0.063%), NIR-AC4 generated strong fluorescence signals in cerebral and tumor blood vessels.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [104]
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- Authors
- Ou, Y., Xiang, H., Yang, X., Wang, R., Huan, S., Yuan, L., Ren, T., & Zhang, X.
- Affiliations
- State Key Laboratory of Chemo and Biosensing College of Chemistry and Chemical Engineering Hunan University Hunan University Changsha 410082 P.R. China
- Hunan University (CN)
- Corresponding author
- Ren, Tian‐Bing
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2025-03-30
- Volume
- 64
- Issue
- 22
- Pages
- e202423978-e202423978
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W4408701632
- Cited by
- 29
- References
- 46
- Citations by year
- 2026: 22 · 2025: 7
- FWCI
- 6.13
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- Angewandte Chemie International Edition (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Natural Science Foundation of China (22374039, 22234003)
- Natural Science Foundation of Hunan Province (2023JJ20004)
- Fundamental Research Funds for the Central Universities (531118010753)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
- Physical Sciences › Engineering › Biomedical Engineering › Nanoplatforms for cancer theranostics
- Keywords
- heptamethine cyanine, emission redshift, large Stokes shift, HOMO-LUMO gap, dye stability, deep tissue imaging, nanoparticle surface modification, tumor imaging, multicolor imaging, in vivo imaging
- MeSH terms
- Animals, Carbocyanines, Fluorescent Dyes, Humans, Infrared Rays, Molecular Structure, Mice, Nanoparticles, Optical Imaging
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Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
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