College of Chemistry and Chemical Engineering, Key Laboratory of Functional Inorganic Materials of Anhui Province, Anhui University, Hefei 230039, PR China.
Institutes of Physical Science and Information Technology, Anhui University, PR China.
Bioorg Chem. 2021 May;110:104789. doi: 10.1016/j.bioorg.2021.104789. Epub 2021 Mar 4.
TD-DFT quantum calculation was performed to predict and/or illustrate the electronic transition, the related absorption and emission maxima of some pyrrole-difluoroboron derivatives with different electron donor-acceptor unit or π-conjugated degree. Upon the calculated results, a new near infrared (NIR) fluorophore (abbreviated as TPBD-BP) was designed and fabricated through linking triphenylamine and pyrrole-difluoroboron units to benzothiadiazole (BTD) backbone. The fluorescence of TPBD-BP in solid state centered at 932 nm, which was 985 nm for TPBD-BP nanoparticles (TPBD-BP dots) encapsulated in PEG-6000. The fluorescence of TPBD-BP in both solid state and dots exhibited off-peak tail emission to NIR-II region (extended to 1300 nm). The TPBD-BP dots showed excellent water solubility, biocompatibility and aggregation induced emission (AIE), which was suitable to be applied in vivo imaging. NIR-II emission signal of TPBD-BP dots can be observed in the reproductive organ of normal nude mice after tail vein injection. This attractive combination of computational and experimental investigation would help to develop new-typed small-molecular NIR fluorophores.
采用 TD-DFT 量子计算方法对一些具有不同电子给体-受体单元或π共轭程度的吡咯二氟化硼衍生物的电子跃迁、相关吸收和发射最大值进行预测和/或说明。根据计算结果，通过将三苯胺和吡咯二氟化硼单元连接到苯并噻二唑（BTD）主链上，设计并制备了一种新型近红外（NIR）荧光团（缩写为 TPBD-BP）。TPBD-BP 在固态中的荧光中心位于 932nm，而在 PEG-6000 包裹的 TPBD-BP 纳米粒子（TPBD-BP 点）中则为 985nm。TPBD-BP 在固态和点中的荧光都表现出向近红外二区（延伸至 1300nm）的非峰尾发射。TPBD-BP 点具有出色的水溶性、生物相容性和聚集诱导发射（AIE）特性，适用于体内成像。TPBD-BP 点的近红外二区发射信号可在正常裸鼠的生殖器官中经尾静脉注射后观察到。这种计算和实验研究的吸引人的组合将有助于开发新型小分子近红外荧光团。
