Bright and Stable NIR‐II J‐Aggregated AIE Dibodipy‐Based Fluorescent Probe for Dynamic In Vivo Bioimaging

Zhang, Qisong; Yu, Peng; Fan, Yong; Sun, Chia‐Chung; He, Haisheng; Li, Xuan; Lu, Lingfei; Zhao, Mengyao; Zhang, Hongxin; Zhang, Fan

doi:10.1002/anie.202012427

Cited by 136 publications

(102 citation statements)

References 98 publications

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“… 50 , 51 For instance, J-aggregates of indocyanine green show Φ F = 3 × 10 –4 with an emission maximum at 890 nm, 52 cyanine dyes have Φ F = 0.05, 53 and dibodipy J-aggregates demonstrate Φ F = 0.03 at 920 nm. 54 …”

Section: Resultsmentioning

confidence: 99%

Exciton Delocalization Counteracts the Energy Gap: A New Pathway toward NIR-Emissive Dyes

Cravcenco

Edhborg

et al. 2021

J. Am. Chem. Soc.

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Exciton coupling between the transition dipole moments of ordered dyes in supramolecular assemblies, so-called J/H-aggregates, leads to shifted electronic transitions. This can lower the excited state energy, allowing for emission well into the near-infrared regime. However, as we show here, it is not only the excited state energy modifications that J-aggregates can provide. A bay-alkylated quaterrylene was synthesized, which was found to form J-aggregates in 1,1,2,2-tetrachloroethane. A combination of superradiance and a decreased nonradiative relaxation rate made the J-aggregate four times more emissive than the monomeric counterpart. A reduced nonradiative relaxation rate is a nonintuitive consequence following the 180 nm (3300 cm −1 ) red-shift of the J-aggregate in comparison to the monomeric absorption. However, the energy gap law, which is commonly invoked to rationalize increased nonradiative relaxation rates with increasing emission wavelength, also contains a reorganization energy term. The reorganization energy is highly suppressed in J-aggregates due to exciton delocalization, and the framework of the energy gap law could therefore reproduce our experimental observations. J-Aggregates can thus circumvent the common belief that lowering the excited state energies results in large nonradiative relaxation rates and are thus a pathway toward highly emissive organic dyes in the NIR regime.

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Section: Resultsmentioning

confidence: 99%

Exciton Delocalization Counteracts the Energy Gap: A New Pathway toward NIR-Emissive Dyes

Cravcenco

Edhborg

et al. 2021

J. Am. Chem. Soc.

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“…Therefore, the development of NIR‐II small‐molecule organic fluorophores is of great interest in the fields of bioimaging and chemical research (J. Cao et al, 2020; Lei et al, 2019; Y. Sun, Qu, et al, 2016; Q. Zhang et al, 2021; M. Zhao et al, 2021). Although the development of small organic molecule‐based NIR‐II fluorophores is conceptually straightforward, design and synthesis are complex in reality, which is a major roadblock in the development of such agents (Ding et al, 2018; Schnermann, 2017).…”

Section: Classification Of Nir‐ii Fluorophoresmentioning

confidence: 99%

“…Therefore, the development of NIR-II small-molecule organic fluorophores is of great interest in the fields of bioimaging and chemical research (J. Cao et al, 2020;Lei et al, 2019;Q. Zhang et al, 2021;.…”

Section: Small Organic Molecule-based Fluorescent Dyesmentioning

confidence: 99%

Unlocking the power of optical imaging in the second biological window: Structuring near‐infrared II materials from organic molecules to nanoparticles

Dahal

Ray

Pan

2021

WIREs Nanomed Nanobiotechnol

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Biomedical imaging techniques play a crucial role in clinical diagnosis, surgical intervention, and prognosis. Fluorescence imaging in the second biological window (second near‐infrared [NIR‐II]; 1000–1700 nm) has attracted attention recently. NIR‐II fluorescence imaging offers unique advantages in terms of reduced photon scattering, deep tissue penetration, high sensitivity, and many others. A host of materials, including small organic molecules, single‐walled carbon nanotubes, polymeric and rare‐earth‐doped nanoparticles, have been explored as NIR‐II emitting fluorescent probes. Efficient and viable approaches to design and develop fluorescence probes with tunable photophysical properties without compromising other key features are of paramount importance. Various chemical strategies are explored to increase the quantum yield of these imaging agents without compromising their spatiotemporal resolution, specificity, and tissue penetration capabilities. This review summarizes the strategies implemented to design and synthesize NIR‐II emitting nanoparticles and small organic molecule‐based fluorescent probes for applications in the biomedical field. This article is categorized under: Diagnostic Tools > In Vivo Nanodiagnostics and Imaging Implantable Materials and Surgical Technologies > Nanoscale Tools and Techniques in Surgery

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“…AIEgens commonly show enhanced emission in the aggregated state, which is mainly attributed to the restriction of intramolecular motions. AIEgens have made great contributions to bioimaging applications, especially those in the ll OPEN ACCESS near-infrared (NIR) window, by regulating multi-hierarchical structures from single-molecule to molecular aggregates (Liu et al, 2020;Xu et al, 2020b;Zhang et al, 2020;Zhao et al, 2020). AIE effect endows molecules with high fluorescence efficiency while the TICT effect enables a red-shifted emission and enhanced non-radiative relaxation (Li et al, 2015(Li et al, , 2017.…”

Section: Introductionmentioning

confidence: 99%

Hypoxia-activated probe for NIR fluorescence and photoacoustic dual-mode tumor imaging

et al. 2021

iScience

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Construction of tumor microenvironment responsive probe with more than one imaging modality, in particular toward hypoxia of solid tumors, is an appealing yet significantly challenging task. In this work, we designed a hypoxia-activated probe TBTO (Triphenylamine-Benzothiadiazole-Triphenylamine derivative featuring four diethylamino N-Oxide groups) for in vivo imaging. TBTO could undergo bioreduction in a hypoxic microenvironment to yield compound TBT sharing both near-infrared (NIR) aggregation-induced emission and strong twisted intramolecular charge transfer features, which endows the probe with excellent performance in NIR fluorescence and photoacoustic dual-mode tumor imaging. This study offers useful insights into designing a new generation agent for clinical cancer diagnosis.

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Bright and Stable NIR‐II J‐Aggregated AIE Dibodipy‐Based Fluorescent Probe for Dynamic In Vivo Bioimaging

Cited by 136 publications

References 98 publications

Exciton Delocalization Counteracts the Energy Gap: A New Pathway toward NIR-Emissive Dyes

Exciton Delocalization Counteracts the Energy Gap: A New Pathway toward NIR-Emissive Dyes

Unlocking the power of optical imaging in the second biological window: Structuring near‐infrared II materials from organic molecules to nanoparticles

Hypoxia-activated probe for NIR fluorescence and photoacoustic dual-mode tumor imaging

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