4,8-Bis(5-bromo-2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazole | 1323953-37-2

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 环羧酸
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 4,8-Bis(5-bromo-2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazole
• 英文别名: 2,8-bis(5-bromo-2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl)-5λ4,11-dithia-4,6,10,12-tetrazatricyclo[7.3.0.03,7]dodeca-1(12),2,4,5,7,9-hexaene
• CAS: 1323953-37-2
• 化学式: C₁₈H₈Br₂N₄O₄S₄
• 分子量: 632.358
• InChiKey: CQRDDXBXVRFOAL-UHFFFAOYSA-N

物化性质

• 沸点：
  749.8±70.0 °C(Predicted)
• 密度：
  2.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  173
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4,8-Bis(5-bromo-2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazole 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Donor–Acceptor–Donor-based π-Conjugated Oligomers for Nonlinear Optics and Near-IR Emission

  摘要：

  A family of multi-heterocycle donor acceptor donor (DAD) telechelic conjugated oligomers designed for two-photon absorption (2PA) and emission in the near-infrared (near-IR) were prepared, and the relationship between their spectral, structural, and electrochemical properties were investigated. These oligomers, based on electron-rich thiophene, phenylene, and 3,4-ethylenedioxythiophene (EDOT) units as donors along with electron-deficient benzothiadiazole or its derivative units as acceptors, have been characterized through linear absorbance and fluorescence measurements, nonlinear absorbance, cyclic voltammetry, and differential pulse voltammetry to demonstrate the evolution of narrow HOMO-LUMO gaps ranging from 1.05 to 1.95 eV, with the oligomers composed of EDOT and benzo[1,2-c,3,4-c']bis[1,2,5]thiadiazole (BBT) exhibiting the narrowest gap. The absorption maxima ranges from 517 to 846 nm and the fluorescence maxima ranges from 651 to 1088 nm for the different oligomers. Z-scan and two-photon fluorescence were used to measure the frequency degenerate 2PA of the different oligomers. The oligomer's 2PA cross sections ranged from 900-3500 GM, with the oligomer containing EDOT donor units and a BBT acceptor unit exhibiting the largest 2PA cross section. The use of these oligomers in red to near-IR emitting polymer light-emitting diodes (PLEDs) was demonstrated by blending the soluble emitting oligomers into a suitable host matrix. Energy transfer from the matrix to the emitting oligomer can be achieved, resulting in PLEDs with pure oligomer emission.

  DOI：

  10.1021/cm201424a
• 作为产物：
  描述：

  4,8-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 以93%的产率得到4,8-Bis(5-bromo-2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazole
  参考文献：
  名称：

  Donor–Acceptor–Donor-based π-Conjugated Oligomers for Nonlinear Optics and Near-IR Emission

  摘要：

  A family of multi-heterocycle donor acceptor donor (DAD) telechelic conjugated oligomers designed for two-photon absorption (2PA) and emission in the near-infrared (near-IR) were prepared, and the relationship between their spectral, structural, and electrochemical properties were investigated. These oligomers, based on electron-rich thiophene, phenylene, and 3,4-ethylenedioxythiophene (EDOT) units as donors along with electron-deficient benzothiadiazole or its derivative units as acceptors, have been characterized through linear absorbance and fluorescence measurements, nonlinear absorbance, cyclic voltammetry, and differential pulse voltammetry to demonstrate the evolution of narrow HOMO-LUMO gaps ranging from 1.05 to 1.95 eV, with the oligomers composed of EDOT and benzo[1,2-c,3,4-c']bis[1,2,5]thiadiazole (BBT) exhibiting the narrowest gap. The absorption maxima ranges from 517 to 846 nm and the fluorescence maxima ranges from 651 to 1088 nm for the different oligomers. Z-scan and two-photon fluorescence were used to measure the frequency degenerate 2PA of the different oligomers. The oligomer's 2PA cross sections ranged from 900-3500 GM, with the oligomer containing EDOT donor units and a BBT acceptor unit exhibiting the largest 2PA cross section. The use of these oligomers in red to near-IR emitting polymer light-emitting diodes (PLEDs) was demonstrated by blending the soluble emitting oligomers into a suitable host matrix. Energy transfer from the matrix to the emitting oligomer can be achieved, resulting in PLEDs with pure oligomer emission.

  DOI：

  10.1021/cm201424a

文献信息

• NIR‐II Conjugated Electrolytes as Biomimetics of Lipid Bilayers for In Vivo Liposome Tracking
  作者：Yingying Meng、Ji Gao、Peirong Zhou、Xudong Qin、Miao Tian、Xiaohui Wang、Cheng Zhou、Kai Li、Fei Huang、Yong Cao

  DOI：10.1002/anie.202318632

  日期：2024.3.22

  Liposomes serve as promising and versatile vehicles for drug delivery. Tracking these nanosized vesicles, particularly in vivo, is crucial for understanding their pharmacokinetics. This study introduces the design and synthesis of three new conjugated electrolyte (CE) molecules, which emit in the second near‐infrared window (NIR‐II), facilitating deeper tissue penetration. Additionally, these CEs, acting as biomimetics of lipid bilayers, demonstrate superior compatibility with lipid membranes compared to commonly used carbocyanine dyes like DiR. To counteract the aggregation‐caused quenching effect, CEs employ a twisted backbone, as such their fluorescence intensities can effectively enhance after a fluorophore multimerization strategy. Notably, a “passive” method was employed to integrate CEs into liposomes during the liposome formation, and membrane incorporation efficiency was significantly promoted to nearly 100%. To validate the in vivo tracking capability, the CE‐containing liposomes were functionalized with cyclic arginine‐glycine‐aspartic acid (cRGD) peptides, serving as tumor‐targeting ligands. Clear fluorescent images visualizing tumor site in living mice were captured by collecting the NIR‐II emission. Uniquely, these CEs exhibit additional emission peak in visible region, enabling in vitro subcellular analysis using routine confocal microscopy. These results underscore the potential of CEs as a new‐generation of membrane‐targeting probes to facilitate the liposome‐based medicine research.
• CN115385935
  申请人：——

  公开号：——

  公开（公告）日：——