Shortwave Infrared Imaging with J-Aggregates Stabilized in Hollow Mesoporous Silica Nanoparticles

Chen, Wei; Cheng, Chi‐An; Cosco, Emily D.; Ramakrishnan, S.; Lingg, Jakob G. P.; Bruns, Oliver T.; Zink, Jeffrey I.; Sletten, Ellen M.

doi:10.26434/chemrxiv.7503506

Cited by 3 publications

(3 citation statements)

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“…Increasing cyanine NIR-II dyes have appeared in academic literature through structure redesigning or modifying. [70,71] The cyclohexene can also be replaced by cyclopentene or other derivatives, e.g., IR-806, IR-797, IR-140, etc. NIR-II tail emission of part of NIR-I dyes was observed.…”

Section: Nir-i/ii Polymethine/cyanine Dyesmentioning

confidence: 99%

Near‐Infrared‐II Molecular Dyes for Cancer Imaging and Surgery

et al. 2019

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Fluorescence bioimaging affords a vital tool for both researchers and surgeons to molecularly target a variety of biological tissues and processes. This review focuses on summarizing organic dyes emitting at a biological transparency window termed the near‐infrared‐II (NIR‐II) window, where minimal light interaction with the surrounding tissues allows photons to travel nearly unperturbed throughout the body. NIR‐II fluorescence imaging overcomes the penetration/contrast bottleneck of imaging in the visible region, making it a remarkable modality for early diagnosis of cancer and highly sensitive tumor surgery. Due to their convenient bioconjugation with peptides/antibodies, NIR‐II molecular dyes are desirable candidates for targeted cancer imaging, significantly overcoming the autofluorescence/scattering issues for deep tissue molecular imaging. To promote the clinical translation of NIR‐II bioimaging, advancements in the high‐performance small molecule–derived probes are critically important. Here, molecules with clinical potential for NIR‐II imaging are discussed, summarizing the synthesis and chemical structures of NIR‐II dyes, chemical and optical properties of NIR‐II dyes, bioconjugation and biological behavior of NIR‐II dyes, whole body imaging with NIR‐II dyes for cancer detection and surgery, as well as NIR‐II fluorescence microscopy imaging. A key perspective on the direction of NIR‐II molecular dyes for cancer imaging and surgery is also discussed.

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Section: Nir-i/ii Polymethine/cyanine Dyesmentioning

confidence: 99%

Near‐Infrared‐II Molecular Dyes for Cancer Imaging and Surgery

et al. 2019

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“…In addition to the polymeric encapsulation, other methods are also available for the bioimaging. Sletten and co-workers 45 successfully employed hollow mesoporous silica nanoparticles (HMSNs) to load the IR-140 photosensitizer (Figure 6a). As mentioned earlier, the dye IR-140 formed a special J-aggregation under the guidance of a quantum dot template enabling a larger than 165 nm of absorption red-shift to the NIR-II region.…”

Section: Fluorescence and Photoacoustic Imagingmentioning

confidence: 99%

Assembly Induced Super-Large Red-Shifted Absorption: The Burgeoning Field of Organic Near-Infrared Materials

2021

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Supramolecular assembly of organic dye compounds with J-aggregation leads to a red-shifted absorption spectrum that greatly facilitates the construction of near-infrared (NIR) materials. A considerable improvement of the material functions requires that the absorption red-shift be larger than 100 nm, but such a super-large red-shift is challenging, and the rules leading to the super-large red-shifted absorption is still not explicit. In this review, we focused on those J-aggregated organic dye materials with super-large red-shifted absorption. The nature of the super-large red-shift is originated from the intermolecular charge transfer between neighboring chromophores. The super-large red-shift can be obtained by tuning either the molecular structure or kinetic assembly process in a delicate manner. Materials with super-large red-shifted absorption have been successfully applied to biological imaging, phototherapy, electronic devices, and solar cells, and show great potential in many other fields. The elaboration of assembly induced super-large red-shifted absorption is promising for design of supramolecular NIR materials with tuned structures, enhanced functionalities, and a wide array of applications.

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“…[25][26][27] Bene ting from these unique characteristics of J-aggregates, J-aggregation is becoming a facile way to achieve NIR-II uorescence. Elegant examples of NIR-II emissive J-aggregates of cyanine and squaraine dyes were given by Sletten, 28 Zhang, 29 , and Fan 23 groups. However, advances in the J-aggregates with NIR-II emission are rather slow in comparison with uorophores developed based on molecular engineering strategy due to the lack of diversi ed Jaggregate uorescent dyes.…”

Section: Introductionmentioning

confidence: 99%

J-Aggregates of meso- [2.2] Paracyclophanyl-BODIPY Dye for NIR-II Imaging

Liu

Duan

et al. 2020

Preprint

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J-aggregation has been proved to be an efficient strategy for the development of fluorescent imaging agents in the second near-infrared (NIR-II, 1000–1700 nm) window. However, the design of NIR-II 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 the first example of BODIPY dye with J-aggregation induced NIR-II fluorescence. PCP-BDP2 shows emission maximum at 795 nm in diluted solution and NIR-II emission at 1010 nm in the J-aggregation state. Mechanism studies reveal that the steric and conjugation effect of the PCP group on the BODIPY core plays key roles in the J-aggregation behavior and NIR-II fluorescence tuning. Notably, NIR-II emissive J-aggregates of PCP-BDP2 can be efficiently stabilized in the assembled nanoparticle. Taking advantage of high quantum yield and good photo-/chemo-stability, J-aggregates of PCP-BDP2 show high-resolution and long-term in vivo NIR-II imaging ability. Furthermore, J-aggregates of PCP-BDP2 can be utilized for lymph node imaging and fluorescence-guided surgery in the nude mouse, which demonstrates their potential clinical application. This study not only demonstrates BODIPY dye as a new J-aggregation platform for developing NIR-II imaging agents but also encourages further exploration on J-aggregation induced NIR-II emission of the other conventional organic dyes.

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Shortwave Infrared Imaging with J-Aggregates Stabilized in Hollow Mesoporous Silica Nanoparticles

Cited by 3 publications

References 1 publication

Near‐Infrared‐II Molecular Dyes for Cancer Imaging and Surgery

Near‐Infrared‐II Molecular Dyes for Cancer Imaging and Surgery

Assembly Induced Super-Large Red-Shifted Absorption: The Burgeoning Field of Organic Near-Infrared Materials

J-Aggregates of meso- [2.2] Paracyclophanyl-BODIPY Dye for NIR-II Imaging

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