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 | 1003593-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 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
• 英文别名: 2,8-Bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-5lambda4,11-dithia-4,6,10,12-tetrazatricyclo[7.3.0.03,7]dodeca-1(12),2,4,5,7,9-hexaene；2,8-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-5λ4,11-dithia-4,6,10,12-tetrazatricyclo[7.3.0.03,7]dodeca-1(12),2,4,5,7,9-hexaene
• CAS: 1003593-65-4
• 化学式: C₁₈H₁₀N₄O₄S₄
• 分子量: 474.566
• InChiKey: SKYYNHPVQWZDLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 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(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazole 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 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：

  4,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)benzo[c][1,2,5]thiadiazole-5,6-diamine 在 三甲基氯硅烷 、 N-亚磺酰苯胺 作用下， 以 吡啶 为溶剂， 以84%的产率得到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
  参考文献：
  名称：

  Low band gap EDOT–benzobis(thiadiazole) hybrid polymer characterized on near-IR transmissive single walled carbon nanotube electrodes

  摘要：

  由双EDOT和苯并双(噻二唑)重复单元组成的电子供体/受体Ï-共轭聚合物呈现出两种还原现象，其带隙范围在±0.5至0.8 eV之间，具体取决于带隙的测定方法。

  DOI：

  10.1039/b709672k

文献信息

• TEST STRIP FOR SHORT-WAVE NEAR INFRARED IMMUNOFLUORESCENCE CHROMATOGRAPHIC DETECTION AND USE THEREOF
  申请人：WWHS BIOTECH, INC.

  公开号：US20200166501A1

  公开（公告）日：2020-05-28

  Provided are a test strip for short-wave near infrared immunofluorescence chromatographic detection, a system for immunofluorescence chromatographic detection and a method for quantifying an analyte in a sample. The test strip for short-wave near infrared immunofluorescence chromatographic detection includes: a body, defining a sample region, a binding region, a detecting region and an adsorbing region connected with one another sequentially; a first antibody, labeled with a fluorescent microsphere, coated on the binding region and configured to specifically recognize an analyte; a detecting line and a quality control line, located in the detecting region, wherein the detecting line closes to the binding region; a second antibody, coated on the detecting line and configured to specifically recognize the analyte; and a third antibody, coated on the quality control line and configured to specifically recognize the first antibody, in which the fluorescent microsphere is a near-infrared II polymer fluorescent microsphere.
• NEAR-INFRARED II POLYMER FLUORESCENT MICROSPHERE AND METHOD FOR PREPARING SAME
  申请人：NIRMIDAS BIOTECH, INC.

  公开号：US20200181485A1

  公开（公告）日：2020-06-11

  Provided are a near-infrared II polymer fluorescent microsphere and a method for preparing the same. The method includes steps of 1) dissolving fluorochrome in a water-immiscible organic solvent, thus obtaining a fluorochrome solution; 2) distributing a polymer microsphere into a sodium dodecyl sulfonate solution, thus obtaining a microsphere solution with the polymer microsphere as a carrier for the fluorochrome; 3) subjecting a first mixture of the fluorochrome solution and the microsphere solution to ultrasonic treatment, thus obtaining an emulsion; 4) swelling the emulsion such that the fluorochrome solution enters nanopores formed during swelling of the polymer microsphere, thus obtaining a second mixture; and 5) heating the second mixture to volatilize the organic solvent, such that the fluorochrome is crystallized out and encapsulated in the nanopores, thus obtaining the near-infrared II polymer fluorescent microsphere.
• [EN] NEAR-INFRARED II POLYMER FLUORESCENT MICROSPHERE AND METHOD FOR PREPARING SAME<br/>[FR] MICROSPHÈRE FLUORESCENTE EN POLYMÈRE PROCHE INFRAROUGE II ET SON PROCÉDÉ DE PRÉPARATION
  申请人：WWHS BIOTECH INC

  公开号：WO2019019472A1

  公开（公告）日：2019-01-31

  Provided are a near-infrared II polymer fluorescent microsphere and a method for preparing the same. The method includes steps of 1) dissolving fluorochrome in a water-immiscible organic solvent, thus obtaining a fluorochrome solution; 2) distributing a polymer microsphere into a sodium dodecyl sulfonate solution, thus obtaining a microsphere solution with the polymer microsphere as a carrier for the fluorochrome; 3) subjecting a first mixture of the fluorochrome solution and the microsphere solution to ultrasonic treatment, thus obtaining an emulsion; 4) swelling the emulsion such that the fluorochrome solution enters nanopores formed during swelling of the polymer microsphere, thus obtaining a second mixture; and 5) heating the second mixture to volatilize the organic solvent, such that the fluorochrome is crystallized out and encapsulated in the nanopores, thus obtaining the near-infrared II polymer fluorescent microsphere.
• NIR‐II Conjugated Electrolytes as Biomimetics of Lipid Bilayers for <i>In Vivo</i> 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.
• Donor–Acceptor–Donor-based π-Conjugated Oligomers for Nonlinear Optics and Near-IR Emission
  作者：Stefan Ellinger、Kenneth R. Graham、Pengjie Shi、Richard T. Farley、Timothy T. Steckler、Robert N. Brookins、Prasad Taranekar、Jianguo Mei、Lazaro A. Padilha、Trenton R. Ensley、Honghua Hu、Scott Webster、David J. Hagan、Eric W. Van Stryland、Kirk S. Schanze、John R. Reynolds

  DOI：10.1021/cm201424a

  日期：2011.9.13

  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.