A Water‐Soluble, NIR‐Absorbing Quaterrylenediimide Chromophore for Photoacoustic Imaging and Efficient Photothermal Cancer Therapy

Liu, Chang; Zhang, Shaobo; Li, Jianhao; Wei, Jie; Müllen, Kläus; Yin, Meizhen

doi:10.1002/anie.201810541

Cited by 235 publications

(160 citation statements)

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“…Later, acoustic imaging of 4T1 murine breast cancer cells in BALB/c mice analysed wherein the inserted QDI nanoparticles enter the blood circulation and collect at the tumors within the tissues. Thus, the high photoacoustic intensities and relatively less size of QDI nanoparticles support the usage as phototheranostic and photodynamic agents in cancer cell treatment (Figure ) . increase in amplitude.…”

Section: Utilization Of External Stimuli Sourcesmentioning

confidence: 81%

Recent Advances on Stimuli‐Responsive Smart Materials and their Applications

2019

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Stimuli‐responsive materials have raised major attention in digital technology, sensors and biomedical applications owing to quick response towards external stimuli, for example light, voltage, pressure, temperature, mechanical friction and pH. Nevertheless, action of external stimuli on organic materials affects their internal physico‐chemical properties and facilitates improved thermal/photo stability, tuning detection sensitivity, accuracy and biocompatibility. This review article highlights recent progress on stimuli‐responsive materials with mixed valence species, viologens, twisting chirality, crystalline/amorphous, sol‐gel phase transitions and resulting supramolecular nanostructures via non‐covalent interactions. These materials can be applied in flexible electronics, drug delivery, detection of pollutants and bioimaging. Thus, the demand for widespread research on development of stimuli‐responsive materials are requisite to resolve the challenges pertaining to stability and sensitivity of devices for design in comprehensive technology.

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Section: Utilization Of External Stimuli Sourcesmentioning

confidence: 81%

Recent Advances on Stimuli‐Responsive Smart Materials and their Applications

2019

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“…Based on this value, the photothermal conversion efficiency of THPG vesicles was calculated to be 44.1% by combining the Eqs. 1-4 (shown in the methods) 16,[35][36][37] . It is higher than most of the organic photothermal agents reported in literatures 4 .…”

Section: Preparation and Characterization Of Thpg Polymer Vesiclesmentioning

confidence: 99%

In situ supramolecular polymerization-enhanced self-assembly of polymer vesicles for highly efficient photothermal therapy

et al. 2020

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Vesicular photothermal therapy agents (PTAs) are highly desirable in photothermal therapy (PTT) for their excellent light-harvesting ability and versatile hollow compartments. However, up to now, the reported vesicular PTAs are generally self-assembled from small molecules like liposomes, and polymer vesicles have seldom been used as PTAs due to the unsatisfactory photothermal conversion efficiency resulting from the irregular packing of chromophores in the vesicle membranes. Here we report a nano-sized polymer vesicle from hyperbranched polyporphyrins with favorable photothermal stability and extraordinarily high photothermal efficiency (44.1%), showing great potential in imaging-guided PTT for tumors through in vitro and in vivo experiments. These excellent properties are attributed to the in situ supramolecular polymerization of porphyrin units inside the vesicle membrane into well-organized 1D monofilaments driven by π-π stacking. We believe the supramolecular polymerization-enhanced self-assembly process reported here will shed a new light on the design of supramolecular materials with new structures and functions.

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“…Compared with fruitful researches of oligorylene-bisimides for organic devices and single molecular spectroscopy [1][2][3][4][5][6], genuine oligorylenes have been sporadically investigated mainly because of their synthetic difficulty and low solubility ( Figure 1) [7]. To be applied to electronic or photovoltaic components, the scalable synthesis of pure soluble compounds is essential.…”

Section: Introductionmentioning

confidence: 99%

Direct borylation of terrylene and quaterrylene

Kano

Uehara

Matsuo

et al. 2020

Beilstein J. Org. Chem.

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The preparation of large rylenes often needs the use of solubilizing groups along the rylene backbone, and all the substituents of the terrylenes and quaterrylenes were introduced before creating the rylene skeleton. In this work, we successfully synthesized 2,5,10,13-tetrakis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)terrylene (TB4) by using an iridium-catalyzed direct borylation of C–H bonds in terrylene in 56% yield. The product is soluble in common organic solvents and could be purified without column chromatography. Single crystal X-ray diffraction analysis revealed that the terrylene core is not disturbed by the substituents and is perfectly flat. The photophysical properties of TB4 are also unchanged by the substituents because the carbon atoms at 2,5,10,13-positions have less coefficients on its HOMO and LUMO, estimated by theoretical calculations. Finally, the same borylation reaction was applied for quaterrylene, resulting in the formation of soluble tetra-borylated quaterrylene despite a low yield. The post modification of rylenes enables us to prepare their borylated products as versatile units after creating the rylene skeletons.

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A Water‐Soluble, NIR‐Absorbing Quaterrylenediimide Chromophore for Photoacoustic Imaging and Efficient Photothermal Cancer Therapy

Cited by 235 publications

References 41 publications

Recent Advances on Stimuli‐Responsive Smart Materials and their Applications

Recent Advances on Stimuli‐Responsive Smart Materials and their Applications

In situ supramolecular polymerization-enhanced self-assembly of polymer vesicles for highly efficient photothermal therapy

Direct borylation of terrylene and quaterrylene

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