Efficient Red/Near‐Infrared Fluorophores Based on Benzo[1,2‐b:4,5‐b′]dithiophene 1,1,5,5‐Tetraoxide for Targeted Photodynamic Therapy and In Vivo Two‐Photon Fluorescence Bioimaging,Advanced Functional Materials

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Efficient Red/Near‐Infrared Fluorophores Based on Benzo[1,2‐b:4,5‐b′]dithiophene 1,1,5,5‐Tetraoxide for Targeted Photodynamic Therapy and In Vivo Two‐Photon Fluorescence Bioimaging
Advanced Functional Materials ( IF 18.5 ) Pub Date : 2018-01-26 , DOI: 10.1002/adfm.201706945
Shijie Zhen ₁ , Shaowei Wang ₂ , Shiwu Li ₁ , Wenwen Luo ₁ , Meng Gao ₁ , Lai Guan Ng ₃ , Chi Ching Goh ₃ , Anjun Qin ₁ , Zujin Zhao ₁ , Bin Liu ₂ , Ben Zhong Tang _{1,

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Affiliation

Red/near‐infrared dyes are highly demanded for biological applications but most of them are far from satisfactory. In this work, a series of red/near‐infrared fluorophores based on electron‐withdrawing benzo[1,2‐b:4,5‐b′]dithiophene 1,1,5,5‐tetraoxide (BDTO) are synthesized and characterized. They possess both aggregation‐induced emission, and hybridized local and charge‐transfer characteristics. Crystallographic, spectroscopic, electrochemical and computational results reveal that the oxidation of benzo[1,2‐b:4,5‐b′]dithiophene to BDTO can endow the fluorophores with greatly red‐shifted emission, enhanced emission efficiency, reduced energy levels, enlarged two‐photon absorption cross section, and increased reactive oxygen species generation efficiency. The nanoparticles fabricated with a near‐infrared fluorophore TPA‐BDTO show high photostability and biocompatibility with good performance in targeted photodynamic ablation of cancer cells and two‐photon fluorescence imaging of intravital mouse brain vasculature.

中文翻译：

基于苯并[1,2-b：4,5-b']二噻吩1,1,5,5-四氧化钛的高效红/近红外荧光团用于靶向光动力疗法和体内双光子荧光生物成像

红色/近红外染料对生物应用有很高的要求，但大多数都不令人满意。在这项工作中，合成并表征了一系列基于吸电子苯并[1,2- b：4,5- b ']二噻吩1,1,5,5-四氧化物（BDTO）的红色/近红外荧光团。它们既具有聚集引起的发射，又具有混合的局部和电荷转移特征。晶体学，光谱学，电化学和计算结果表明，苯并[1,2- b：4,5- b′]二噻吩与BDTO的结合可以使荧光团具有极大的红移发射，增强的发射效率，降低的能级，增大的两个光子吸收截面以及增加的活性氧生成效率。用近红外荧光团TPA-BDTO制成的纳米颗粒具有很高的光稳定性和生物相容性，在癌细胞的靶向光动力消融和活体小鼠脑血管的双光子荧光成像中表现出良好的性能。

更新日期：2018-01-26

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