4,8-bis[4-(1,2,2-triphenylethenyl)phenyl]-2|E4|A2-Benzo[1,2-c:4,5-c']bis[1,2,5]thiadiazole | 1378502-49-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 4,8-bis[4-(1,2,2-triphenylethenyl)phenyl]-2|E4|A2-Benzo[1,2-c:4,5-c']bis[1,2,5]thiadiazole
• 英文别名: 2,8-bis[4-(1,2,2-triphenylethenyl)phenyl]-5λ4,11-dithia-4,6,10,12-tetrazatricyclo[7.3.0.03,7]dodeca-1(12),2,4,5,7,9-hexaene
• CAS: 1378502-49-8
• 化学式: C₅₈H₃₈N₄S₂
• 分子量: 855.099
• InChiKey: AMAHGJAWKSVISU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.1
• 重原子数：
  64
• 可旋转键数：
  10
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-溴苯甲酰苯 在 bis-triphenylphosphine-palladium(II) chloride 、 正丁基锂 、 三甲基氯硅烷 、 N-sulfinylaniline 、 铁粉 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 氯仿 为溶剂， 反应 80.33h， 生成 4,8-bis[4-(1,2,2-triphenylethenyl)phenyl]-2|E4|A2-Benzo[1,2-c:4,5-c']bis[1,2,5]thiadiazole
  参考文献：
  名称：

  Efficient Non-doped Near Infrared Organic Light-Emitting Devices Based on Fluorophores with Aggregation-Induced Emission Enhancement

  摘要：

  A family of donor-acceptor-donor (D-A-D) type near-infrared (NIR) fluorophores containing rigid nonplanar conjugated tetraphenylethene (TPE) moieties was designed and synthesized through Stifle coupling reactions with electron-deficient [1,2,5]thiadiazolo[3,4-g]quinoxaline (QTD) or benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazole (BBTD) as acceptors. The absorption, fluorescence, and electrochemical properties were studied. These compounds exhibited good aggregation-induced emission enhancement (AIEE) property, as a result of the twisted TPE units, which restrict the intramolecular rotation and reduce the pi-pi stacking. Photoluminescence of these chromophores ranges from 600 to 1100 nm, and their HOMO-LUMO gaps are between 1.85 and 1.50 eV. Non-doped organic light-emitting diodes (OLEDs) based on these fluorophores were made and exhibited EL emission spectra peaking from 706 to 864 nm. The external quantum efficiency (EQE) of these devices ranged from 0.89% to 0.20% and remained fairly constant over a range of current density of 100-300 mA cm(-2). The device with the highest solid fluorescence efficiency emitter la shows the best performance with a maximum radiance of 2917 mW Sr-1 m(-2) and EQE of 0.89%. A contrast between nondoped and doped OLEDs with these materials confirms that AIEE compounds are suitable for fabricate efficient nondoped NIR OLEDs.

  DOI：

  10.1021/cm3008733

文献信息

• Luminogens for biological applications
  申请人：THE HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY

  公开号：US11186586B2

  公开（公告）日：2021-11-30

  A compound comprises a donor and an acceptor, wherein at least one donor (“D”) and at least one acceptor (“A”) may be arranged in an order of D-A; D-A-D; A-D-A; D-D-A-D-D; A-A-D-A-A; D-A-D-A-D; and A-D-A-D-A. The compound may be selected from the group consisting of: MTPE-TP, MTPE-TT, TPE-TPA-TT, PTZ-BT-TPA, NPB-TQ, TPE-TQ-A, MTPE-BTSe, DCDPP-2TPA, DCDPP-2TPA4M, DCDP-2TPA, DCDP-2TPA4M, TTS, ROpen-DTE-TPECM, and RClosed-DTE-TPECM. The compound may be used as a probe and may be functionalized with special targeted groups to image biological species. As non-limiting examples, the compound may be used in cellular cytoplasms or tissue imaging, blood vessel imaging, in vivo fluorescence imaging, brain vascular imaging, sentinel lymph node mapping, and tumor imaging, and the compound may be used as a photoacoustic agent.

  一种化合物由供体和受体组成，其中至少一个供体（"D"）和至少一个受体（"A"）可以按照 D-A；D-A-D；A-D-A；D-D-A-D-D；A-A-D-A；D-A-D-A-D；和 A-D-A-D-A 的顺序排列。该化合物可选自由以下组成的组：MTPE-TP、MTPE-TT、TPE-TPA-TT、PTZ-BT-TPA、NPB-TQ、TPE-TQ-A、MTPE-BTSe、DCDPP-2TPA、DCDPP-2TPA4M、DCDP-2TPA、DCDP-2TPA4M、TTS、ROpen-DTE-TPECM 和 RClosed-DTE-TPECM。化合物可用作探针，也可与特殊的靶向基团官能化，以成像生物物种。作为非限制性实例，该化合物可用于细胞胞浆或组织成像、血管成像、体内荧光成像、脑血管成像、前哨淋巴结绘图和肿瘤成像，该化合物还可用作光声剂。
• LUMINOGENS FOR BIOLOGICAL APPLICATIONS
  申请人：THE HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY

  公开号：US20220048923A1

  公开（公告）日：2022-02-17

  A compound comprises a donor and an acceptor, wherein at least one donor (“D”) and at least one acceptor (“A”) may be arranged in an order of D-A; D-A-D; A-D-A; D-D-A-D-D; A-A-D-A-A; D-A-D-A-D; and A-D-A-D-A. The compound may be selected from the group consisting of: MTPE-TP, MTPE-TT, TPE-TP A-TT, PTZ-BT-TP A, NPB-TQ, TPE-TQ-A, MTPE-BTSe, DCDPP-2TP A, DCDPP-2TPA4M, DCDP-2TPA, DCDP-2TPA4M, TTS, ROpen-DTE-TPECM, and RClosed-DTE-TPECM. The compound may be used as a probe and may be functionalized with special targeted groups to image biological species. As non-limiting examples, the compound may be used in cellular cytoplasms or tissue imaging, blood vessel imaging, in vivo fluorescence imaging, brain vascular imaging, sentinel lymph node mapping, and tumor imaging, and the compound may be used as a photoacoustic agent.
• Efficient Non-doped Near Infrared Organic Light-Emitting Devices Based on Fluorophores with Aggregation-Induced Emission Enhancement
  作者：Xiaobo Du、Ji Qi、Zhiqiang Zhang、Dongge Ma、Zhi Y. Wang

  DOI：10.1021/cm3008733

  日期：2012.6.12

  A family of donor-acceptor-donor (D-A-D) type near-infrared (NIR) fluorophores containing rigid nonplanar conjugated tetraphenylethene (TPE) moieties was designed and synthesized through Stifle coupling reactions with electron-deficient [1,2,5]thiadiazolo[3,4-g]quinoxaline (QTD) or benzo[1,2-c;4,5-c']bis[1,2,5]thiadiazole (BBTD) as acceptors. The absorption, fluorescence, and electrochemical properties were studied. These compounds exhibited good aggregation-induced emission enhancement (AIEE) property, as a result of the twisted TPE units, which restrict the intramolecular rotation and reduce the pi-pi stacking. Photoluminescence of these chromophores ranges from 600 to 1100 nm, and their HOMO-LUMO gaps are between 1.85 and 1.50 eV. Non-doped organic light-emitting diodes (OLEDs) based on these fluorophores were made and exhibited EL emission spectra peaking from 706 to 864 nm. The external quantum efficiency (EQE) of these devices ranged from 0.89% to 0.20% and remained fairly constant over a range of current density of 100-300 mA cm(-2). The device with the highest solid fluorescence efficiency emitter la shows the best performance with a maximum radiance of 2917 mW Sr-1 m(-2) and EQE of 0.89%. A contrast between nondoped and doped OLEDs with these materials confirms that AIEE compounds are suitable for fabricate efficient nondoped NIR OLEDs.