Donor Engineering for NIR-II Molecular Fluorophores with Enhanced Fluorescent Performance

Yang, Qinglai; Hu, Zhubin; Zhu, Shoujun; Ma, Rui; Ma, Haiying; Ma, Zhuoran; Wan, Hao; Zhu, Tong; Jiang, Zhengyan; Liu, Weiqiang; Jiao, Liying; Sun, Haitao; Liang, Yongye; Dai, Hongjie

doi:10.1021/jacs.7b10334

Cited by 438 publications

(363 citation statements)

References 76 publications

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“…When the water fraction in THF/water mixture gradually elevates to above 60 %, the PL intensities of both TPE‐Ph‐B and TPE‐Th‐B tremendously increase due to the formation of aggregates resulting in RIM, showing representative AIE feature. For TPE‐ETh‐B, as the oxygen‐containing ETh group enhances the water‐solubility of the whole molecule, water cannot serve as a desirable poor solvent. As a result, dimethyl sulphoxide (DMSO)/toluene were used as the good/poor solvent pair.…”

Section: Resultsmentioning

confidence: 99%

Far‐Red/Near‐Infrared Emissive (1,3‐Dimethyl)barbituric Acid‐Based AIEgens for High‐Contrast Detection of Metastatic Tumors in the Lung

Hong

Bao

Dai

et al. 2018

Chemistry An Asian Journal

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Despite of the enthusiastic research in aggregation‐induced emission luminogens (AIEgens) in recent years, the ones that can be smoothly used for sophisticated biomedical applications such as in vivo bioimaging of pulmonary metastatic tumors during surgery are still limited. Herein, we report the design and synthesis of a new series of far‐red/near‐infrared (FR/NIR) fluorescent AIEgens that consist of methoxy‐substituted tetraphenylethene (TPE) as the electron‐donating moiety, (1,3‐dimethyl)barbituric acid as the electron‐withdrawing moiety, and different π‐bridge units. As compared to benzene or 3,4‐ethylenedioxythiophene, using thiophene as the π‐conjugation unit between the donor and acceptor results in a relatively higher absolute fluorescence quantum yield (14.5 %) in water when formulating the corresponding AIEgens into nanoparticles (AIE dots) with an amphiphilic co‐polymer as the doping matrix. The highly FR/NIR‐emissive thiophene‐based AIE dots are demonstrated to be potent for intraoperative detection of pulmonary metastatic tumors, particularly the micro‐sized ones, with excellent signal‐to‐background ratio.

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Section: Resultsmentioning

confidence: 99%

Far‐Red/Near‐Infrared Emissive (1,3‐Dimethyl)barbituric Acid‐Based AIEgens for High‐Contrast Detection of Metastatic Tumors in the Lung

Hong

Bao

Dai

et al. 2018

Chemistry An Asian Journal

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“…Further, dialkyl substituted fluorene is employed as a shielding unit to introduce into the central DAD core to prevent the interaction with water. These strategies open up new avenues for developing a series of high bright NIR‐II fluorophores, of which the optimized one displays fluorescence emission peaked at 1048 nm with a QY of 5.3% in water . Despite long side chains being capable of reducing intermolecular interactions, they are found to also trigger molecular motions in aggregates, whose nonradiative decay spoils fluorescence QY .…”

Section: Introductionmentioning

confidence: 99%

Constitutional Isomerization Enables Bright NIR‐II AIEgen for Brain‐Inflammation Imaging

Liu

Chen

et al. 2019

Adv Funct Materials

213

209

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The shortage of high quantum yield (QY) organic fluorophores in the second near‐infrared window (NIR‐II) has become a bottleneck in bioimaging field. Now, a simple strategy is proposed to address this: constitutional isomerization on the basis of the molecular design philosophy of aggregation‐induced emission. With the combination of backbone distortion and rotor twisting, the resultant NIR‐II fluorophore 2TT‐oC6B displays an emission peak at 1030 nm and a QY of 11% in nanoparticles, one of the highest reported so far. Control molecules confirm that the distorted backbone and twisted rotors play equally important roles in determining the fluorescence properties of the NIR‐II fluorophores. To allow for the targeting ability to reach deeply located diseases, neutrophils (NEs) are used to penetrate the brain tissues and accumulate in the inflammation site. Herein, it is shown that NEs carrying 2TT‐oC6B nanoparticles can penetrate the blood‐brain‐barrier and visualize the deeply located inflammation through an intact scalp and skull. Notably, the bright 2TT‐oC6B contributes to a significantly enhanced signal‐to‐background ratio of 30.6 in the brain inflammation site.

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“…Based on the shielding unit–donor–acceptor–donor–shielding unit (S‐D‐A‐D‐S) backbone, we developed a series of NIR‐II fluorophores by tuning the donor units and side chains on the shielding unit and identified a super bright D‐A‐D dye with high quantum yield (QY) of ≈6.0% in water. In vivo imaging studies showed that IR‐FD had high tumor retention . PbS/CdS core/shell quantum dots (QDs) with dense polymer coating were selected for NIR‐IIb imaging to visualize cancer‐associated sentinel LNs.…”

mentioning

confidence: 99%

Multiplexed NIR‐II Probes for Lymph Node‐Invaded Cancer Detection and Imaging‐Guided Surgery

et al. 2020

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Tumor‐lymph node (LN) metastasis is the dominant prognostic factor for tumor staging and therapeutic decision‐making. However, concurrently visualizing metastasis and performing imaging‐guided lymph node surgery is challenging. Here, a multiplexed‐near‐infrared‐II (NIR‐II) in vivo imaging system using nonoverlapping NIR‐II probes with markedly suppressed photon scattering and zero‐autofluorescence is reported, which enables visualization of the metastatic tumor and the tumor metastatic proximal LNs resection. A bright and tumor‐seeking donor–acceptor–donor (D‐A‐D) dye, IR‐FD, is screened for primary/metastatic tumor imaging in the NIR‐IIa (1100–1300 nm) window. This optimized D‐A‐D dye exhibits greatly improved quantum yield of organic D‐A‐D fluorophores in aqueous solutions (≈6.0%) and good in vivo performance. Ultrabright PbS/CdS core/shell quantum dots (QDs) with dense polymer coating are used to visualize cancer‐invaded sentinel LNs in the NIR‐IIb (>1500 nm) window. Compared to clinically used indocyanine green, the QDs show superior brightness and photostability (no obvious bleaching even after continuous laser irradiation for 5 h); thus, only a picomolar dose is required for sentinel LNs detection. This combination of dual‐NIR‐II image‐guided surgery can be performed under bright light, adding to its convenience and appeal in clinical use.

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Donor Engineering for NIR-II Molecular Fluorophores with Enhanced Fluorescent Performance

Cited by 438 publications

References 76 publications

Far‐Red/Near‐Infrared Emissive (1,3‐Dimethyl)barbituric Acid‐Based AIEgens for High‐Contrast Detection of Metastatic Tumors in the Lung

Far‐Red/Near‐Infrared Emissive (1,3‐Dimethyl)barbituric Acid‐Based AIEgens for High‐Contrast Detection of Metastatic Tumors in the Lung

Constitutional Isomerization Enables Bright NIR‐II AIEgen for Brain‐Inflammation Imaging

Multiplexed NIR‐II Probes for Lymph Node‐Invaded Cancer Detection and Imaging‐Guided Surgery

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