Croconaine Rotaxane Dye with 984 nm Absorption: Wavelength‐Selective Photothermal Heating

McGarraugh, Hannah H.; Liu, Wenqi; Matthews, Braden; Smith, Bradley D.

doi:10.1002/ejoc.201900082

Cited by 11 publications

(4 citation statements)

References 36 publications

(67 reference statements)

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“…So far, most of the reported croconaines have absorption peaks in the NIR-I region . Although their absorption can be tuned by introducing large planar donors, − this strategy remains difficult to push the absorption to the NIR-II range. It is also reported that croconic acid reacts with phenolic hydroxyl groups on both sides after ring opening occurs, obtaining an NIR-II-absorbing isomerized product, but its yield and molar absorption coefficient are both very low.…”

Section: Introductionmentioning

confidence: 99%

Chalcogen Atom-Modulated Croconaine for Efficient NIR-II Photothermal Theranostics

Chen,

Ma,

Yang

et al. 2024

ACS Appl. Mater. Interfaces

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Organic dye-based agents with near-infrared (NIR)-II absorption have great potential for cancer theranostics because of the deeper tissue penetration and good biocompatibility. However, proper design is required to develop NIR-IIabsorbing dyes with good optical properties. We proposed to construct chalcogen atom-modulated croconaine for NIR-II light-triggered photothermal theranostics. By introducing different chalcogen atoms (O, S, Se, or Te) into the structure of croconaine, the light absorption of croconaine can be precisely regulated from the NIR-I to the NIR-II range due to the heavy-atom effect. Especially, Te-substituted croconaine (CRTe) and its nanoformulations exhibit superior NIR-II responsiveness, a high photothermal conversion efficiency (70.6%), and good photostability. With their favorable tumor accumulation, CRTe-NPs from tumor regions can be visualized by NIR-II optoacoustic systems with high resolution and high contrast; meanwhile, their superior photothermal performance also contributes to efficient cell killing and tumor elimination upon 1064 nm laser irradiation. Therefore, this work provides an efficient strategy for the molecular design of NIR-II organic photothermal agents.

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Section: Introductionmentioning

confidence: 99%

Chalcogen Atom-Modulated Croconaine for Efficient NIR-II Photothermal Theranostics

Chen,

Ma,

Yang

et al. 2024

ACS Appl. Mater. Interfaces

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“…Dyes and pigments featuring rotaxane topologies are known in the scientific community and find application as nanoscale switches in molecular electronics amongst others. [ 1 , 2 , 3 , 4 , 5 ] In this work, we investigate a supramolecular photovoltaics approach to rectify charge propagation in solar cells through the use of rotaxane sensitizers.…”

Section: Introductionmentioning

confidence: 99%

Rotaxane‐Functionalized Dyes for Charge‐Rectification in p‐Type Photoelectrochemical Devices

Bouwens,

Bakker,

Zhu

et al. 2023

Advanced Science

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A supramolecular photovoltaic strategy is applied to enhance power conversion efficiencies (PCE) of photoelectrochemical devices by suppressing electron–hole recombination after photoinduced electron transfer (PET). Here, the author exploit supramolecular localization of the redox mediator—in close proximity to the dye—through a rotaxane topology, reducing electron–hole recombination in p‐type dye‐sensitized solar cells (p‐DSSCs). Dye PRotaxane features 1,5‐dioxynaphthalene recognition sites (DNP‐arms) with a mechanically‐interlocked macrocyclic redox mediator naphthalene diimide macrocycle (3‐NDI‐ring), stoppering synthetically via click chemistry. The control molecule PStopper has stoppered DNP‐arms, preventing rotaxane formation with the 3‐NDI‐ring. Transient absorption and time‐resolved fluorescence spectroscopy studies show ultrafast (211 ± 7 fs and 2.92 ± 0.05 ps) PET from the dye‐moiety of PRotaxane to its mechanically interlocked 3‐NDI‐ring‐acceptor, slowing down the electron–hole recombination on NiO surfaces compared to the analogue . p‐DSSCs employing PRotaxane (PCE = 0.07%) demonstrate a 30% PCE increase compared to PStopper (PCE = 0.05%) devices, combining enhancements in both open‐circuit voltages (VOC = 0.43 vs 0.36 V) and short‐circuit photocurrent density (JSC = −0.39 vs −0.34 mA cm−2). Electrochemical impedance spectroscopy shows that PRotaxane devices exhibit hole lifetimes (τh) approaching 1 s, a 16‐fold improvement compared to traditional I−/I3−‐based systems (τh = 50 ms), demonstrating the benefits obtained upon nanoengineering of interfacial dye‐regeneration at the photocathode.

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“…The alteration of metabolic state in tumor tissue results in peculiar extracellular chemical composition, which leads to the TME being slightly more acidic (pH 6.5–7.0) than normal tissues . The absorption of some NIR organic dyes could be readily tuned in the acidic environment, thus proving to be potentially pH-sensitive PA contrast agents. − Recently, pH-sensitive Croc dyes exhibited strong NIR absorption and intense photothermal conversion efficiency with remarkable chemical and thermal stability, making them a promising agent for PA as well as PTT. − However, their poor solubility in aqueous solution hinders in vivo biomedical use . There are reports on chemical modification of Croc dyes to improve their biocompatibility through self-assembled HSA-Croc NPs and PEGylation of CR780 (a Croc dye) NPs for PA imaging and PTT. , …”

Section: Introductionmentioning

confidence: 99%

pH-Triggered Poly(ethylene glycol)–Poly(lactic acid/glycolic acid)/Croconaine Nanoparticles-Assisted Multiplexed Photoacoustic Imaging and Enhanced Photothermal Cancer Therapy

Lui

et al. 2021

ACS Appl. Bio Mater.

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The most advantageous and attractive property of photoacoustic imaging is its capability to visualize and differentiate multiple species according to their unique absorbance profiles simultaneously in a single mixture. We here report the pH-sensitive near-infrared (NIR) croconaine (Croc) dyes-loaded copolymeric PEG−PLGA nanoparticles (NPs) for in vivo multiplexed PA imaging and pH-responsive photothermal therapy (PTT) in an orthotopic xenograft model. PEG chains on the polymeric NPs shell were conjugated with iRGD in another set of NPs to realize efficient tumor targeting. The distribution and the intensity of two sets of iRGD-targeted and nontargeted NPs inside tumors are simultaneously imaged and monitored in vivo. Meanwhile, the utilization of iRGD-targeted PPC 815 NPs as a pH-active photothermal agent with promising tumor-inhibition efficacy was demonstrated. As a result, this nanoplatform is capable of assisting multiwavelength unmixing of PA imaging as well as providing remarkable photothermal ablation for anticancer treatment.

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Croconaine Rotaxane Dye with 984 nm Absorption: Wavelength‐Selective Photothermal Heating

Cited by 11 publications

References 36 publications

Chalcogen Atom-Modulated Croconaine for Efficient NIR-II Photothermal Theranostics

Chalcogen Atom-Modulated Croconaine for Efficient NIR-II Photothermal Theranostics

Rotaxane‐Functionalized Dyes for Charge‐Rectification in p‐Type Photoelectrochemical Devices

pH-Triggered Poly(ethylene glycol)–Poly(lactic acid/glycolic acid)/Croconaine Nanoparticles-Assisted Multiplexed Photoacoustic Imaging and Enhanced Photothermal Cancer Therapy

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