4,4'-(3,4-dinitrothiophene-2,5-diyl)bis(N,N-diphenylaniline) | 851233-21-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4,4'-(3,4-dinitrothiophene-2,5-diyl)bis(N,N-diphenylaniline)
• 英文别名: 4-[3,4-dinitro-5-[4-(N-phenylanilino)phenyl]thiophen-2-yl]-N,N-diphenylaniline
• CAS: 851233-21-1
• 化学式: C₄₀H₂₈N₄O₄S
• 分子量: 660.753
• InChiKey: RCMLLUPIIDZUPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  49
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,4'-(3,4-dinitrothiophene-2,5-diyl)bis(N,N-diphenylaniline) 在 盐酸 、 锌 作用下， 生成 2,5-bis(4-(diphenylamino)-phenyl)thiophene-3,4-diamine
  参考文献：
  名称：

  基于吡嗪衍生物控制D–A–D发色团中的电荷转移

  摘要：

  一系列带有各种吸电子基团的对称供体-受体-供体（D–A–D）发色团，例如喹喔啉（Qx），苯并[ g ]喹喔啉（BQ），吩嗪（Pz），苯并[ b ]吩嗪（BP），噻吩并[3,4- b ]吡嗪（TP）和噻吩并[3,4- b ]喹喔啉（TQ），已经过设计和合成。由于吡嗪环中两个亚胺氮的吸电子特性和两个三苯胺中另外两个胺氮的给电子性，可以发现所有发色团的分子内电荷转移（ICT）相互作用。苯环或噻吩环在吡嗪受体单元上融合后，ICT相互作用会增强，导致ICT的红移。此外，噻吩环在扩大ICT相互作用和扩大吸收光谱方面优于苯环。通常，将噻吩环稠合在DQxD的Qx单元上时，可以在简单的生色团DTQD中实现近红外染料，在716 nm处显示最大吸收波长，阈值超过900 nm。如理论计算所揭示的，这可能是由于受体部分上电荷密度的提高和更好的轨道重叠。这些结果表明，在垂直于D–A–D主链的方向上扩展吡嗪受体的共轭可显着改善ICT相互作用。

  DOI：

  10.1021/jo500856k
• 作为产物：
  描述：

  2,5-二溴-3,4-二硝基噻吩 、 4-硼酸三苯胺 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 16.0h， 以84%的产率得到4,4'-(3,4-dinitrothiophene-2,5-diyl)bis(N,N-diphenylaniline)
  参考文献：
  名称：

  Synthesis and Spectroscopic Characterization of Thienopyrazine-Based Fluorophores for Application in Luminescent Solar Concentrators (LSCs)

  摘要：

  有机荧光物质已经广泛应用于硅光伏发电中作为发射体。特别是，具有强烈光吸收能力，深红和近红外区域发射以及大斯托克斯位移值的有机共轭系统的制备是一项非常具有挑战性的任务。在这里，我们报告了一种简单易行的方法，可以基于噻吩吡嗪核心制备三种对称给体-受体-给体（DAD）有机发射材料。三种染料中的中心核心通过引入芳香基团进行了修饰，旨在影响它们的光学性质。这些荧光物质通过光谱研究进行了表征。在所有情况下，发现可见-近红外发射和大斯托克斯位移，突出了这些分子作为LSC应用的有希望的材料。

  DOI：

  10.3390/molecules26185428

文献信息

• [EN] LUMINOGENS FOR BIOLOGICAL APPLICATIONS<br/>[FR] LUMINOGÈNES POUR APPLICATIONS BIOLOGIQUES
  申请人：UNIV HONG KONG SCI & TECH

  公开号：WO2018108070A1

  公开（公告）日：2018-06-21

  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.

  一种化合物包括一个给体和一个受体，其中至少一个给体（"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-A；D-A-D-A-D；和A-D-A-D-A的顺序排列。该化合物可从以下组中选择：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。该化合物可以用作探针，并且可以与特定的靶向基团功能化以成像生物物种。作为非限制性示例，该化合物可以用于细胞质或组织成像、血管成像、体内荧光成像、脑血管成像、前哨淋巴结映射和肿瘤成像，并且该化合物可以用作光声剂。
• Boosting Photoacoustic Effect via Intramolecular Motions Amplifying Thermal‐to‐Acoustic Conversion Efficiency for Adaptive Image‐Guided Cancer Surgery
  作者：Heqi Gao、Xingchen Duan、Di Jiao、Yi Zeng、Xiaoyan Zheng、Jingtian Zhang、Hanlin Ou、Ji Qi、Dan Ding

  DOI：10.1002/anie.202109048

  日期：2021.9.13

  Photoacoustic (PA) imaging emerges as a promising technique for biomedical applications. The development of new strategies to boost PA conversion without depressing other properties (e.g., fluorescence) is highly desirable for multifunctional imaging but difficult to realize. Here, we report a new phenomenon that active intramolecular motions could promote PA signal by specifically increasing thermal-to-acoustic

  光声 (PA) 成像是一种很有前途的生物医学应用技术。开发新策略以促进 PA 转换而不抑制其他特性（例如，荧光）对于多功能成像是非常理想的，但很难实现。在这里，我们报告了一种新现象，即主动分子内运动可以通过专门增加热-声转换效率来促进 PA 信号。具有强烈分子内运动的化合物通过提高热-声转换表现出放大的 PA 信号，并且由于聚集诱导的发射特征，荧光也增加。TPA-TQ3 NP 同时具有高 PA 和荧光亮度，可实现精确的图像引导手术。术前荧光和PA成像能够以高对比度的方式定位原位乳腺肿瘤，术中荧光成像描绘微小的残留肿瘤。这项研究突出了分子内运动放大 PA 效应的新设计指南。
• 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。
• Band gap tunable for near-infrared absorbing chromophores with multi-triphenylamine and tris (thieno)hexaazatriphenylenes acceptors
  作者：Baoxiang Gao、Defang Xia、Yanhou Geng、Yanxiang Cheng、Lixiang Wang

  DOI：10.1016/j.tetlet.2010.02.039

  日期：2010.4

  Two disk-like D-A type chromophores with multi-triphenylamine donors and hexaazatriphenylenes acceptors were synthesized and fully characterized by H-1 and C-13 NMR, elemental analysis and mass spectrometry. The effects of the hexaazatriphenylene oil the optical and electrochemical properties and band gap of the chromophores were investigated. As the hexaazatriphenylene core fused with three thiophene rings, the band gaps of the compounds Could be tuned from 1.65 eV to 1.15 eV. The pi-pi* absorption peak and charge-transfer absorption peak of the hexaazatriphenylene Compounds were Fed shifted from visible spectrum region (393 and 530 nm) to near-infrared spectrum region (542 and 756 nm). In addition, clue to an increase in the pi electronic Coupling between electron donor and electron acceptor, the extinction coefficient (charge-transfer absorption) of the hexaazatriphenylene compound decreases 85% from 3.4 x 10(4) mol(-1) dm(-3) cm(-1) to 0.5 x 10(4) mol (1) dm (3) cm (1). (C) 2010 Elsevier Ltd. All rights reserved.
• LUMINOGENS FOR BIOLOGICAL APPLICATIONS
  申请人：THE HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY

  公开号：US20200079787A1

  公开（公告）日：2020-03-12

  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.