A thieno-isoindigo derivative-based conjugated polymer nanoparticle for photothermal therapy in the NIR-II bio-window

Wei, Zuwu; Xue, Fangqing; Xin, Fuli; Wu, Ming; Wang, Bingxi; Zhang, Xiaolong; Yang, Sen; Guo, Zhiyong; Liu, Xiaolong

doi:10.1039/d0nr03771k

“…In particular, PTAs with NIR‐II (1000–1700 nm) absorbing ability are aroused immense attention due to their minimized photo‐toxicity to healthy tissue and deeper tissue penetration comparing to NIR‐I (700–1000 nm) absorbing PTAs. So far, few numbers of NIR‐II absorbing PTAs based on inorganic materials, [5–16] conjugated polymer NPs [17–26] and supramolecular radicals [27, 28] have been developed, however, these PTAs still suffer from the long‐term safety concern and low reproducibility. Small organic NIR‐II absorbing PTAs are proposed to be the most promising PTAs due to their better biocompatibility and higher biodegradability comparing to inorganic and conjugated polymer PTAs.…”

Section: Introductionmentioning

confidence: 99%

A Borondifluoride‐Complex‐Based Photothermal Agent with an 80 % Photothermal Conversion Efficiency for Photothermal Therapy in the NIR‐II Window

Jiang

¹

,

Zhang

²

,

Wang

³

et al. 2021

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Small organic photothermal agents (SOPTAs) that absorb in the second near‐infrared (NIR‐II, 1000–1700 nm) window are highly desirable in photothermal therapy for their good biocompatibility and deeper tissue penetration. However, the design of NIR‐II absorbing SOPTAs remains a great challenge. Herein, we report that molecular engineering of BF2 complex via strengthening the donor‐acceptor conjugation and increasing the intramolecular motions is an efficient strategy to achieve NIR‐II absorbing SOPTAs with high photothermal performance. Based on this strategy, a BF2 complex, BAF4, was designed and synthesized. BAF4 exhibits an intense absorption maximum at 1000 nm and negligible fluorescence. Notably, the nanoparticles of BAF4 achieve a high photothermal conversion efficiency value of 80 % under 1064 nm laser irradiation (0.75 W cm−2). In vitro and in vivo studies reveal the great potential of BAF4 nanoparticles in photoacoustic imaging‐guided photothermal therapy in the NIR‐II window.

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“…In particular, PTAs with NIR‐II (1000–1700 nm) absorbing ability are aroused immense attention due to their minimized photo‐toxicity to healthy tissue and deeper tissue penetration comparing to NIR‐I (700–1000 nm) absorbing PTAs. So far, few numbers of NIR‐II absorbing PTAs based on inorganic materials, [5–16] conjugated polymer NPs [17–26] and supramolecular radicals [27, 28] have been developed, however, these PTAs still suffer from the long‐term safety concern and low reproducibility. Small organic NIR‐II absorbing PTAs are proposed to be the most promising PTAs due to their better biocompatibility and higher biodegradability comparing to inorganic and conjugated polymer PTAs.…”

Section: Introductionmentioning

confidence: 99%

A Borondifluoride‐Complex‐Based Photothermal Agent with an 80 % Photothermal Conversion Efficiency for Photothermal Therapy in the NIR‐II Window

Jiang

¹

,

Zhang

²

,

Wang

³

et al. 2021

View full text Add to dashboard Cite

Small organic photothermal agents (SOPTAs) that absorb in the second near‐infrared (NIR‐II, 1000–1700 nm) window are highly desirable in photothermal therapy for their good biocompatibility and deeper tissue penetration. However, the design of NIR‐II absorbing SOPTAs remains a great challenge. Herein, we report that molecular engineering of BF2 complex via strengthening the donor‐acceptor conjugation and increasing the intramolecular motions is an efficient strategy to achieve NIR‐II absorbing SOPTAs with high photothermal performance. Based on this strategy, a BF2 complex, BAF4, was designed and synthesized. BAF4 exhibits an intense absorption maximum at 1000 nm and negligible fluorescence. Notably, the nanoparticles of BAF4 achieve a high photothermal conversion efficiency value of 80 % under 1064 nm laser irradiation (0.75 W cm−2). In vitro and in vivo studies reveal the great potential of BAF4 nanoparticles in photoacoustic imaging‐guided photothermal therapy in the NIR‐II window.

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“…Under irradiation at 1064 nm, the SPN exhibited admirable PTT effect with excellent targeting ability for tumor both in vitro and in vivo. [211] In another research, Yang and co-workers reported P169 with thieno-M5 as the acceptor unit. [212] The corresponding SPN exhibited strong absorbance in the NIR-II window with a superior photothermal conversion efficiency of 66.4% under 1064 nm irradiation, thereby leading to efficient PTT performance to cancer cell in vivo.…”

Section: Phototherapymentioning

confidence: 98%

“…[38] Liu and co-workers synthesized P168 based on thieno-M5 (Figure 16). [211] The polymer possessed low optical bandgap with absorption extended to 1100 nm in the NIR-II window ascribing to the intramolecular charge transfer. Then, the surface-functionalized SPN based on P168 was prepared.…”

Section: Phototherapymentioning

confidence: 99%

Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

Wei

¹

,

Zhang

²

,

Yu

³

2021

Adv Funct Materials

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(1 of 33)benzothiadiazole (BT), [8,9] naphthalene diimide (NDI), [10,11] and isoindigo. [12][13][14] Isoindigo is an isomer of the wellknown industrial dye indigo and can be directly isolated from nature. [15,16] The structural difference between isoindigo and indigo is the relative positions of the nitrogen atom and the carbonyl group. In the indigo molecule, the nitrogen atoms are not connected to the carbonyl groups. Moreover, the nitrogen atoms in isoindigo molecule are connected with carbonyl groups. In 2012, indigo was reported as the active layer material of organic fieldeffect transistors (OFETs), which exhibited well-balanced ambipolar transport. [17] However, the H-bonded indigo showed extremely low solubility. For achieving good solution processibility, solubilizing side chains are introduced on the nitrogen atoms, which on the other hand break the intramolecular hydrogen bond, thereby reducing the molecular conjugation and limiting the electronics applications. [18] By contrast, the side chains on isoindigo do not break the hydrogen bond, and thus isoindigo is considered as a superior building block for organic electronic materials. [18,19] Since isoindigo was first used in organic electronics in 2010, [20] isoindigo-derived conjugated polymers have attracted considerable attention and have been developed rapidly due to the strong electron deficiency and high molecular planarity of isoindigo unit. [12,21] Moreover, compared with DPP, BT or NDI, isoindigo has a π-framework that can be readily modified. The structural feature of isoindigo endows itself many modification sites, including the side chains attached to the lactam nitrogen atoms, the center double bond, and the phenyl rings. More than twenty isoindigo derivatives have been reported. [22][23][24][25][26][27][28] Based on isoindigo and its derivatives, various isoindigo-derived conjugated polymers have been synthesized and many of them showed excellent performance. For example, using isoindigo-derived conjugated polymers, the hole and electron mobilities of p-and n-type OFETs have reached 14.4 and 14.9 cm 2 V −1 s −1 , respectively, and some ambipolar OFETs exhibited high hole/electron mobilities of up to 5.97/7.07 cm 2 V −1 s −1 . [29][30][31] The power conversion efficiencies (PCEs) of fullerene-containing organic photovoltaics (OPVs) and all-polymer solar cells (all-PSCs) based on isoindigo-derived polymers have exceeded 10% and 7%, respectively. [32,33] Furthermore, various structural modification

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A thieno-isoindigo derivative-based conjugated polymer nanoparticle for photothermal therapy in the NIR-II bio-window

Abstract: Photothermal therapy (PTT), a powerful tool for non-invasive cancer treatment, has been recognized as an alternative strategy for cancer therapy in clinic, and it is promoted by optical absorbing agents...

Cited by 35 publications

References 48 publications

A Borondifluoride‐Complex‐Based Photothermal Agent with an 80 % Photothermal Conversion Efficiency for Photothermal Therapy in the NIR‐II Window

A Borondifluoride‐Complex‐Based Photothermal Agent with an 80 % Photothermal Conversion Efficiency for Photothermal Therapy in the NIR‐II Window

A Borondifluoride‐Complex‐Based Photothermal Agent with an 80 % Photothermal Conversion Efficiency for Photothermal Therapy in the NIR‐II Window

Semiconducting Polymers Based on Isoindigo and Its Derivatives: Synthetic Tactics, Structural Modifications, and Applications

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