Side Chain Phenyl Isomerization‐Induced Spatial Conjugation for Achieving Efficient Near‐Infrared II Phototheranostic Agents
Abstract
The contradiction of near‐infrared II (NIR‐II) emission and photothermal effects limits the development of phototheranostic agents (PTAs) in many emerging cutting‐edge applications. Organic aggregates present a promising opportunity for the balance of competitive relaxation processes through the manipulation of molecular structure and packing. Herein, side chain phenyl isomerization‐induced spatial conjugation was proposed for constructing A‐D‐A type NIR‐II PTAs with simultaneous enhancement of fluorescence brightness and photothermal properties. Three pairs of mutually isomeric fluorophores, whose phenyls respectively located at the outside (o‐series) and inside (i‐series) of the side chain, were designed and synthesized. The positional isomerization of the phenyl endows the o‐series crystals with strong spatial conjugation between the phenyl group on the side chain and the backbone, as well as interlocked planar network, which is different to that observed in the i‐series. Thus, all o‐series nanoparticles (NPs) exhibit red‐shifted absorption, enhanced NIR‐II emission, and superior photothermal properties than their i‐series counterparts. A prominent member of the o‐series, o‐ITNP NPs, demonstrated efficacy in facilitating NIR‐II angiography, tumor localization, and NIR‐II imaging‐guided tumor photothermal therapy. The success of this side chain phenyl isomerization strategy paves the way for precise control of the aggregation behavior and for further development of efficient NIR‐II PTAs.
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The o- and i-isomers shared similar absorption/emission profiles.
“While o- and i-isomers shared similar absorption/emission profiles”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [189]
Wang et al. devised a phenyl side-chain isomerization approach in six A-D-A fluorophores.
“Wang et al. devised a phenyl side-chain isomerization approach in six A-D-A fluorophores (o-ITNP, i-ITNP, o-ITCT, i-ITCT, o-IDTCT, i-IDTCT) (Fig. 12a)189.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [189]
Nanoparticles derived from the o-series consistently displayed red-shifted absorption, enhanced NIR-II brightness, and superior imaging-guided tumor ablation.
“Nanoparticles derived from o-series consistently displayed red-shifted absorption, enhanced NIR-II brightness, and superior imaging-guided tumor ablation.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [189]
The o-series fluorophores exhibited brighter NIR fluorescence and improved photothermal conversion.
“o-series fluorophores exhibited brighter NIR fluorescence and improved photothermal conversion.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [189]
The enhancement of o-series fluorophores was attributed to conformational restriction introduced by ortho-phenyl substitution, which facilitated conformational locking and spatial conjugation between the side chain and the backbone.
“This enhancement was attributed to the conformational restriction introduced by the ortho-phenyl substitution, which facilitated conformational locking and spatial conjugation between the side chain and the backbone.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [189]
The consequent tighter molecular packing and extended π-conjugation plane enhanced electronic coupling and reduced the HOMO-LUMO gap.
“The consequent tighter molecular packing and extended π-conjugation plane enhanced electronic coupling and reduced the HOMO-LUMO gap.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [189]
These structural changes accelerated both radiative and non-radiative decay pathways, resulting in red-shifted absorption, superior brightness, and enhanced photothermal performance.
“These structural changes accelerated both radiative and non-radiative decay pathways, resulting in red-shifted absorption, superior brightness, and enhanced photothermal performance.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [189]
Cyano derivatives such as malononitrile are essential electron acceptors for designing NIR-II fluorescent probes.
“Cyano derivatives, such as malononitrile, are essential electron acceptors for designing NIR-II fluorescent probes”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [189]
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References 58 · Cited by 26
- Authors
- Li, C., Yao, M., Jiang, G., Feng, L., Wu, Y., Sha, R., Li, Y., Tang, B. Z., & Wang, J.
- Affiliations
- Inner Mongolia University (CN)
- Chinese Academy of Sciences (CN)
- Chinese University of Hong Kong, Shenzhen (CN)
- Corresponding author
- Wang, Jianguo
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2024-11-25
- Volume
- 64
- Issue
- 7
- Pages
- e202419785-e202419785
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W4404207467
- Cited by
- 26
- References
- 58
- Citations by year
- 2026: 14 · 2025: 12
- FWCI
- 2.54
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Angewandte Chemie International Edition (publishedVersion)
- PubMed (publishedVersion)
- Rare & Special e-Zone (The Hong Kong University of Science and Technology) (submittedVersion)
- Funders
- National Natural Science Foundation of China (22161034, 22165020, 22371151, and 22375213)
- China Postdoctoral Science Foundation (GZC20231183)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Engineering › Biomedical Engineering › Nanoplatforms for cancer theranostics
- Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
- Keywords
- organic nanoparticles, photothermal therapy, tumor targeting, fluorescence enhancement, aggregation behavior
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