Synthesis of Near-Infrared-Absorbing Anionic Heptamethine Cyanine Dyes with Trifluoromethyl Groups DOI Creative Commons

Hiroki Masuoka,

Yasuhiro Kubota, Toshiyasu Inuzuka

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(12), P. 4650 - 4650

Published: June 8, 2023

A novel anionic heptamethine cyanine (HMC) dye with two trifluoromethyl groups that selectively absorb near-infrared light is synthesized. When contrasted previously studied HMC dyes substituents such as methyl, phenyl, and pentafluorophenyl groups, the trifluoromethylated displays a red-shifted maximum absorption wavelength (for instance, 948 nm in CH2Cl2) along enhanced photostability. Furthermore, broad region are synthesized by combining cationic counterion.

Language: Английский

Anti‐Quenching NIR‐II J‐Aggregates of Benzo[c]thiophene Fluorophore for Highly Efficient Bioimaging and Phototheranostics DOI
Ka‐Wai Lee,

Yijian Gao,

Wei‐Chih Wei

et al.

Advanced Materials, Journal Year: 2023, Volume and Issue: 35(20)

Published: March 3, 2023

Molecular fluorophores with the second near-infrared (NIR-II) emission hold great potential for deep-tissue bioimaging owing to their excellent biocompatibility and high resolution. Recently, J-aggregates are used construct long-wavelength NIR-II emitters as optical bands show remarkable red shifts upon forming water-dispersible nano-aggregates. However, wide applications in fluorescence imaging impeded by limited varieties of J-type backbone serious quenching. Herein, a bright benzo[c]thiophene (BT) J-aggregate fluorophore (BT6) anti-quenching effect is reported highly efficient phototheranostics. The BT manipulated have Stokes shift over 400 nm aggregation-induced (AIE) property conquering self-quenching issue fluorophores. Upon BT6 assemblies an aqueous environment, absorption 800 1000 boosted more than 41 26 folds, respectively. In vivo visualization whole-body blood vessel imaging-guided phototherapy results verify that NPs agent cancer This work develops strategy precisely properties biomedical applications.

Language: Английский

Citations

108

J‐Aggregation Strategy toward Potentiated NIR‐II Fluorescence Bioimaging of Molecular Fluorophores DOI
Xiaoming Hu,

Caijun Zhu,

Fengwei Sun

et al.

Advanced Materials, Journal Year: 2023, Volume and Issue: 36(1)

Published: Aug. 1, 2023

Molecular fluorophores emitting in the second near-infrared (NIR-II, 1000-1700 nm) window with strong optical harvesting and high quantum yields hold great potential for vivo deep-tissue bioimaging high-resolution biosensing. Recently, J-aggregates are harnessed to engineer long-wavelength NIR-II emitters show unique superiority tumor detection, vessel mapping, surgical navigation, phototheranostics due their bathochromic-shifted bands required slip-stacked arrangement aggregation state. However, despite preliminary progress of theoretical study structure-property relationships, further paradigms remain scarce lack on aggregated fashion. In this effort, how utilize specific molecular structure form packing motifs J-type exciton coupling is emphatically elucidated. First, several regulating strategies achieve containing intermolecular interactions external conditions positively summarized deeply analyzed. Then, recent reports theranostics systematically provide a clear reference direction promoting development organic fluorophores. Eventually, prospective efforts ameliorating clinical practices outlined.

Language: Английский

Citations

68

Exploring and leveraging aggregation effects on reactive oxygen species generation in photodynamic therapy DOI Creative Commons

Zeyan Zhuang,

Jianqing Li,

Pingchuan Shen

et al.

Aggregate, Journal Year: 2024, Volume and Issue: 5(4)

Published: March 10, 2024

Abstract Aggregate‐level photodynamic therapy (PDT) has attracted significant interest and driven substantial advances in multifunction phototheranostic platforms. As exemplified by two typical instances of aggregation‐caused quenching reactive oxygen species (ROS) aggregation‐induced generation ROS, the aggregation effect plays a role on ROS photosensitizers (PSs), which is worthy in‐depth exploration full utilization. However, contrast to well‐developed researches luminescence, studies concerning are currently relatively nascent disjointed stage, lacking guidance from firmly established research paradigm. To advance this regard, review aims at providing consolidated overview fundamental principles status effects generation. Here, can be organized into main facets. One involves comparison between isolated state aggregated state, mainly conducted methods changing solvent environments adding adjuvants given solvent. The other underscores distinctions different aggregate states, consisting three parts, namely within same or categories based classification single‐component multicomponent aggregates. In endeavor, we will present our views current methodologies that explore how affects highlight design strategies leverage optimize PS regiments. We aspire propel advancement platforms accelerate clinical implementation precision medicine, inspire more contributions aggregate‐level photophysics photochemistry, pushing science materials forward.

Language: Английский

Citations

38

Tuning Shortwave‐Infrared J‐aggregates of Aromatic Ring‐Fused Aza‐BODIPYs by Peripheral Substituents for Combined Photothermal and Photodynamic Therapies at Ultralow Laser Power DOI
Xing Guo, Wanle Sheng, Hongfei Pan

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(11)

Published: Jan. 16, 2024

Abstract Achieving photothermal therapy (PTT) at ultralow laser power density is crucial for minimizing photo‐damage and allowing higher maximum permissible skin exposure. However, this requires agents to possess not just superior conversion efficiency (PCE), but also exceptional near‐infrared (NIR) absorptivity. J ‐aggregates, exhibit a significant redshift narrower absorption peak with extinction coefficient. Nevertheless, achieving predictable ‐aggregates through molecular design remains challenge. In study, we successfully induced desirable J‐ aggregation (λ abs max : 968 nm, ϵ: 2.96×10 5 M −1 cm , λ em 972 Φ FL 6.2 %) by tuning electrostatic interactions between π‐conjugated planes manipulating surface potential of aromatic ring‐fused aza‐BODIPY dyes. Notably, controlling the preparation method encapsulating dyes into F‐127 polymer, were able selectively generate H ‐/ respectively. Furthermore, exhibited two controllable morphologies: nanospheres nanowires. Importantly, shortwave‐infrared ‐aggregated nanoparticles impressive PCE 72.9 % effectively destroyed cancer cells mice‐tumors an 0.27 W −2 (915 nm). This phototherapeutic nano‐platform, which generates behavior, can controllably form / H‐ aggregates selectable aggregate morphology, valuable paradigm developing tumor‐treatment density.

Language: Английский

Citations

31

Rational design of CT-coupled J-aggregation platform based on Aza-BODIPY for highly efficient phototherapy DOI Creative Commons
Sheng‐Mei Wu, Wenze Zhang, Chaoran Li

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(16), P. 5973 - 5979

Published: Jan. 1, 2024

We present the first D–A–D aza-BODIPY scaffold to construct CT-coupled J-aggregates, which show promising results for highly efficient phototherapy.

Language: Английский

Citations

24

Recent advances in near-infrared-II organic J-aggregates for bio-applications DOI

Junchao Xu,

Xudong Zheng, Tian‐Bing Ren

et al.

Coordination Chemistry Reviews, Journal Year: 2025, Volume and Issue: 528, P. 216379 - 216379

Published: Jan. 4, 2025

Language: Английский

Citations

4

A stable and biocompatible shortwave infrared nanoribbon for dual-channel in vivo imaging DOI Creative Commons

Cheng Yao,

Ruwei Wei,

Xiao Luo

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Jan. 2, 2025

The shortwave infrared (SWIR) region is an ideal spectral window for next-generation bioimaging to harness improved penetration and reduced phototoxicity. SWIR activity may also be accessed via supramolecular dye aggregation. Unfortunately, development of aggregation remains challenging. We propose a crystal-aided aggregate synthesis (CAASH) approach introduce layer rationality the J-aggregate successful water-soluble JV-aggregate with bisbenzannulated silicon rhodamine scaffold (ESi5). resulting SWIR-aggregates exhibit excellent stabilities toward organic solvents, pH, sonication, photobleaching, thiols, endogenous oxidative species. Notably, aggregates have high structure-dependent melting temperature ca. 330-335 K. In fact, heating/annealing process can exploited reduce disorder. are biocompatible broad potential in vivo fluorescence photoacoustic imaging more. While has applications, stable absorbers/emitters challenging access. Here, authors report J-aggregates bioimaging.

Language: Английский

Citations

3

Ion−π interactions for constructing organic luminescent materials DOI Creative Commons
Guoyu Jiang, Yu Jia, Jianguo Wang

et al.

Aggregate, Journal Year: 2022, Volume and Issue: 3(6)

Published: Oct. 24, 2022

Abstract Organic luminescent materials are one of the research hotspots worldwide. The efficiency these can be tuned by introducing noncovalent interactions. Ion−π interactions, mainly including anion−π interactions and cation−π relatively new but powerful with extensive applications in supramolecular chemistry. use ion−π to fabricate highly is initiated since they were introduced develop aggregation‐induced emission luminogens 2017. Then, this field undergoing through challenging very prospective developments. In minireview, we start a brief introduction then make summary reports on organic fluorescence based room temperature phosphorescence induced bioimaging, imaging‐guided anticancer antibacterial treatment also discussed. challenges prospects using for constructing presented final part. It expected that minireview will provide some guidelines fabricating novel further extend application potential

Language: Английский

Citations

63

Electron-Withdrawing Substituents Enhance the Type I PDT and NIR-II Fluorescence of BODIPY J Aggregates for Bioimaging and Cancer Therapy DOI
Yu Zhu,

Fapu Wu,

Bingbing Zheng

et al.

Nano Letters, Journal Year: 2024, Volume and Issue: 24(27), P. 8287 - 8295

Published: June 28, 2024

Organic dyes with simultaneously boosted near-infrared-II (NIR-II) fluorescence, type I photodynamic therapy (PDT), and photothermal (PTT) in the aggregate state are still elusive due to unclear structure-function relationship. Herein, electron-withdrawing substituents introduced at 5-indolyl positions of BODIPY form tight J-aggregates for enhanced NIR-II fluorescence PDT/PTT. The introduction an electron-rich julolidine group

Language: Английский

Citations

12

Pyrrolopyrrole Cyanine J-Aggregate Nanoparticles with High Near-Infrared Fluorescence Brightness and Photothermal Performance for Efficient Phototheranostics DOI
Yingnan Xu, Xue Meng, Yang Zhao

et al.

ACS Applied Materials & Interfaces, Journal Year: 2024, Volume and Issue: 16(30), P. 39005 - 39020

Published: July 22, 2024

Advanced photosensitizers for high-performance fluorescence imaging-guided photothermal therapy demand excellent near-infrared (NIR) brightness [molar absorption coefficient (ε) × quantum yield (QY)] and exceptional performance [ε conversion efficiency (PCE)]. However, integrating high potent within a single molecule faces formidable challenge. This article proposes method to address this issue by preparing J-aggregate nanoparticles (NPs) using molecules with ε. J-aggregates effectively improve QY induce molecular emission redshift, while ε play crucial role in improving the performance. By optimizing structure based on pyrrolopyrrole cyanine (PPCy), precise control over PCE of PPCy is achieved. Ultimately, PDDO NPs exhibiting superior (ε = 3.32 104 M–1 cm–1) 1.21 105 are identified as photosensitizers. Notably, each parameter represents one highest levels among reported or probes date. The vivo studies demonstrate that possess NIR imaging capabilities remarkable tumor inhibition rates. study provides innovative insights into development multifunctional

Language: Английский

Citations

10