J-aggregates of meso-[2.2]paracyclophanyl-BODIPY dye for NIR-II imaging
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Abstract
J-aggregation is an efficient strategy for the development of fluorescent imaging agents in the second near-infrared window. However, the design of the second near-infrared fluorescent J-aggregates is challenging due to the lack of suitable J-aggregation dyes. Herein, we report meso -[2.2]paracyclophanyl-3,5-bis- N , N -dimethylaminostyrl BODIPY (PCP-BDP2) as an example of BODIPY dye with J-aggregation induced the second near-infrared fluorescence. PCP-BDP2 shows an emission maximum at 1010 nm in the J-aggregation state. Mechanism studies reveal that the steric and conjugation effect of the PCP group on the BODIPY play key roles in the J-aggregation behavior and photophysical properties tuning. Notably, PCP-BDP2 J-aggregates can be utilized for lymph node imaging and fluorescence-guided surgery in the nude mouse, which demonstrates their potential clinical application. This study demonstrates BODIPY dye as an alternate J-aggregation platform for developing the second near-infrared imaging agents.
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In this system, an interaction between PCP and the N,N-dimethylaminophenyl group predominates the molecular packing and plays a key role in the slip-stacking of the BODIPY core.
“In this system, an interaction between PCP and the N,N-dimethylaminophenyl group predominates the molecular packing and plays a key role in the slip-stacking of the BODIPY core.”
From The Pursuit of Shortwave Infrared-Emitting Nanoparticles with Bright Fluorescence through Molecular Design and Excited-State Engineering of Molecular Aggregates (2022) · cites this paper as [118]
The Results section (X-ray single-crystal structure analysis) identifies a C–H…π interaction between the PCP and N,N-dimethylaminophenyl groups as one of three interactions that dominate PCP-BDP2 packing and facilitate J-aggregation. It does not establish that this interaction alone predominates over the other two. (LLM, conf=0.84)
Experimental — accuracy not yet measuredSWIR fluorescence emitted from J-aggregates of BODIPY dye has been demonstrated by introducing a paracyclophenyl (PCP) group to the meso-position of 3,5-bis-N,N-dimethylaminostyryl BODIPY.
“An SWIR fluorescence emitted from J-aggregates of BODIPY dye has been demonstrated by introducing a paracyclophenyl (PCP) group to the meso-position of 3,5-bis-N,N-dimethylaminostyryl BODIPY (Figure 4b).118”
From The Pursuit of Shortwave Infrared-Emitting Nanoparticles with Bright Fluorescence through Molecular Design and Excited-State Engineering of Molecular Aggregates (2022) · cites this paper as [118]
Encapsulation of PCP-BDP2 J-aggregates in Pluronic F-127 yielded spherical nanoparticles (average diameter of 70 nm) with absorption and fluorescence peaks at 750 and 1010 nm, respectively.
“Further, by encapsulation of PCP-BDP2 J-aggregates in Pluronic F-127, spherical nanoparticles (average diameter of 70 nm) with absorption and fluorescence peaks at 750 and 1010 nm, respectively, were obtained.”
From The Pursuit of Shortwave Infrared-Emitting Nanoparticles with Bright Fluorescence through Molecular Design and Excited-State Engineering of Molecular Aggregates (2022) · cites this paper as [118]
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References 61 · Cited by 301
- Authors
- Li, K., Duan, X., Jiang, Z., Ding, D., Chen, Y., Zhang, G.-Q., & Liu, Z.
- Affiliations
- Nanjing Forestry University (CN)
- Nankai University (CN)
- Nanjing University (CN)
- Corresponding author
- Chen, Yuncong
- Zhang, Guo-Qiang
- Liu, Zhipeng
- Venue
- Nature Communications
- Published
- 2021-04-22
- Volume
- 12
- Issue
- 1
- Pages
- 2376-2376
- ISSN
- 2041-1723 (ISSN-L)
- PMC
- PMC8062432
- OpenAlex
- W3153227329
- Cited by
- 301
- References
- 61
- Citations by year
- 2026: 35 · 2025: 54 · 2024: 70 · 2023: 64 · 2022: 61 · 2021: 17
- FWCI
- 16.08
- Type
- journal article
- Language
- en
- Open access
- gold
- doi.org
- Locations
- Nature Communications (publishedVersion, cc-by)
- Research Square (acceptedVersion, cc-by)
- PubMed Central (publishedVersion, cc-by)
- PubMed (publishedVersion)
- RePEc: Research Papers in Economics (submittedVersion)
- DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
- Funders
- National Natural Science Foundation of China (21971115)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
- Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Photochemistry and Electron Transfer Studies
- Keywords
- J-aggregation, BODIPY dyes, NIR-II fluorescence, second near-infrared window, fluorescent imaging agents, lymph node imaging, fluorescence-guided surgery, photophysical properties, nude mice
- MeSH terms
- Intravital Microscopy, Animals, Boron Compounds, Disease Models, Animal, Fluorescence, Fluorescent Dyes, Humans, Infrared Rays, Lymphatic System, Peritoneal Neoplasms, Video-Assisted Surgery, Cell Line, Tumor, Mice, Optical Imaging
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