Semiconductor Polymer with Strong NIR-II Absorption for Photoacoustic Imaging and Photothermal Therapy

Li, Jia; Li, Shun; Yang, Shuo; Liang, Mengke; Jiang, Xiqun; Wu, Wei

doi:10.1021/acsabm.2c00080

Cited by 12 publications

(3 citation statements)

References 35 publications

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“…The prepared TBy probe exhibited an asymmetric structure, which could effectively alleviate the photobleaching situation, as the energy transfer inside the structure is partially reversible. 40 This feature gave the TBy probe more durable imaging ability, which fulfilled the need for high contrast imaging.…”

Section: Design and Synthesis Of The Tby Fluorescencementioning

confidence: 99%

An Asymmetric NIR-II Organic Fluorophore with an Ultra-Large Stokes Shift for Imaging-Guided and Targeted Phototherapy

Li,

Zhou,

Zhou

et al. 2024

ACS Biomater. Sci. Eng.

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NIR-II imaging-guided phototherapy is an attractive, yet challenging, tumor treatment strategy. By monitoring the accumulation of phototherapy reagents at the tumor site through imaging and determining the appropriate therapy window, the therapeutic effect could be significantly improved. Probes with NIR-II (1000−1700 nm) fluorescence emission and a large Stokes shift hold great promise for fluorescence imaging with deep penetration, minimized self-quenching, and high spatiotemporal resolution. However, due to the lack of a suitable molecular framework, the design of a simple small-molecule dye with a large Stokes shift and NIR-II fluorescence emission has rarely been reported. Herein, we prepare an asymmetric D−π−A type NIR-II fluorescence probe (TBy). The probe is incapsulated in an amphiphilic polymer and modified with a fibronectin targeting peptide CREKA, which could recognize the fibrin−fibronectin complex overexpressed in multiple malignant tumors. The nanoparticles thus constructed (TByC-NPs) have maximum fluorescence emission at 1037 nm with a large Stokes shift of 426 nm, which is the largest Stokes shift among organic NIR-II fluorescent dyes reported in the literature. The TByC-NPs exhibit a good NIR-II imaging performance, active tumor targeting, and good photothermal and photodynamic capabilities. In vitro and in vivo studies verify that the TByC nanoplatform shows outstanding biocompatibility for NIR-II imaging-guided phototherapy and provides an excellent antitumor effect.

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Section: Design and Synthesis Of The Tby Fluorescencementioning

confidence: 99%

An Asymmetric NIR-II Organic Fluorophore with an Ultra-Large Stokes Shift for Imaging-Guided and Targeted Phototherapy

Li,

Zhou,

Zhou

et al. 2024

ACS Biomater. Sci. Eng.

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“…Most of these NBPs were synthesized via conventional methods, such as Stille coupling ,− ,− ,− ,− and Suzuki coupling. ,,− ,,,, Although effective and versatile, these methods still face ecological issues such as involvement of toxic organotin compounds and tedious preactivation of C–H bonds. Considering the great potential and rapid advances in organic semiconductors, there is an urgent need to develop a “greener” approach toward the facile and large-scale synthesis of these polymers.…”

Section: Introductionmentioning

confidence: 99%

“…A dual-acceptor design strategy has also been proposed to construct D–A 1 –D–A 2 copolymers. − For instance, a D–A 1 –D–A 2 copolymer consisting of diketopyrrolopyrrole and benzobisthiadiazole exhibited an E g opt of around 0.65 eV and ambipolar charge transport behavior with mobilities of 1.17 cm 2 V –1 s –1 for holes and 1.32 cm 2 V –1 s –1 for electrons . In addition, NBPs containing benzobisthiadiazole and/or thiadiazoloquinoxaline exhibit NIR absorption and may benefit the photovoltaic performance, − photothermal therapy, ,− and fluorescence/photoacoustic imaging. − Other applications include aspects of spin-related phenomena arising from their open-shell character. ,− …”

Section: Introductionmentioning

confidence: 99%

Versatile Protocol of C–H Direct Arylation Coupling Enables the Synthesis of Narrow-Band-Gap Polymers Containing Benzobisthiadiazole or Thiadiazoloquinoxaline Units

et al. 2023

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π-Conjugated narrow-band-gap polymers (NBPs), characterized by their intrinsically electrical, optical, spintronic, and mechanical properties, have attracted broad interest since the development of the first generation of conducting polymers. The current synthesis of NBPs, nevertheless, largely relies on traditional Suzuki or Stille coupling, which often requires preactivation of aryl C–H bonds involving highly flammable organometallic reagents, such as butyl lithium and highly toxic stannyl agents, which are often involved in Stille coupling. Here, we report the synthesis of a series of NBPs consisting of benzobisthiadiazole (BBT) or thiadiazoloquinoxaline (BBQ) units via a “greener chemistry” of direct arylation polymerization (DArP). Free of toxic organotin compounds or extra borylation, our DArP protocol, in the presence of a Pd2(dba)3 catalyst, phosphine ligands, and carboxylic acid additives enables efficient polymerization with monomers of BBT or BBQ with comonomers containing opposite reactive sites. Consequently, a series of donor–acceptor (D–A) or acceptor–acceptor (A–A) alternating copolymers have been synthesized in decent yields and with minimal defects. These polymers with narrow optical band gaps below 1.3 eV can achieve near-infrared (NIR) absorption and fluorescence emission, as well as stable electrochemical performance. Moreover, the scope of open-shell BBT- and BBQ-based polymers has been broadened, including a series of spin density and spin–orbit coupling, as well as tunable electron, hole, or ambipolar charge transport behavior.

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Metal‐Free Catalytic Formation of a Donor‐Acceptor‐Donor Molecule and Its Lewis Acid‐Adduct Singlet Diradical with High‐Efficient NIR‐II Photothermal Conversion

Kong,

Yang,

Sun

et al. 2024

Angewandte Chemie

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We have synthesized a quinone‐incorporated bistriarylamine donor‐acceptor‐donor (D‐A‐D) semiconductor molecule 1 by B(C6F5)3 (BCF) catalyzed C–H/C–H cross coupling via radical ion pair intermediates. Coordination of Lewis acids BCF and Al(ORF)3 (RF = C(CF3)3) to the semiconductor 1 afforded diradical zwitterions 2 and 3 by integer electron transfer. Upon binding to Lewis acids, the LUMO energy of 1 is significantly lowered and the band gap of the semiconductor is significantly narrowed from 1.93 eV (1) to 1.01 eV (2) and 1.06 eV (3). 2 and 3 are rare near‐infrared (NIR) diradical dyes with broad absorption both centered around 1500 nm. By introducing a photo BCF generator, 2 can be generated by light‐dependent control. Furthermore, the integer electron transfer process can also be reversibly regulated via the addition of CH3CN. In addition, the temperature of 2 sharply increased and reached as high as 110 °C in 10 s upon the irradiation of near‐infrared‐II (NIR‐II) laser (1064 nm, 0.7 W cm‐2), exhibiting a fast response to laser. It displays excellent photothermal stability with a photothermal (PT) conversion efficiency of 62.26% and high‐quality PT imaging.

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Semiconductor Polymer with Strong NIR-II Absorption for Photoacoustic Imaging and Photothermal Therapy

Cited by 12 publications

References 35 publications

An Asymmetric NIR-II Organic Fluorophore with an Ultra-Large Stokes Shift for Imaging-Guided and Targeted Phototherapy

An Asymmetric NIR-II Organic Fluorophore with an Ultra-Large Stokes Shift for Imaging-Guided and Targeted Phototherapy

Versatile Protocol of C–H Direct Arylation Coupling Enables the Synthesis of Narrow-Band-Gap Polymers Containing Benzobisthiadiazole or Thiadiazoloquinoxaline Units

Metal‐Free Catalytic Formation of a Donor‐Acceptor‐Donor Molecule and Its Lewis Acid‐Adduct Singlet Diradical with High‐Efficient NIR‐II Photothermal Conversion

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