4-(thiophen-2-yl)benzo[c][1,2,5]thiadiazole

• 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-(thiophen-2-yl)benzo[c][1,2,5]thiadiazole
• 英文别名: 4-thienyl-2,1,3-benzothiadiazole；4-(2-thienyl)-2,1,3-benzothiadiazole；4-Thiophen-2-yl-2,1,3-benzothiadiazole
• 化学式: C₁₀H₆N₂S₂
• 分子量: 218.303
• InChiKey: ZCRYWFWUORDZCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(thiophen-2-yl)benzo[c][1,2,5]thiadiazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 4.08h， 以85%的产率得到4-(5-bromothiophen-2-yl)benzo[c][1,2,5]thiadiazole
  参考文献：
  名称：

  Synthesis and Optoelectronic Properties of 6,12-Bis(amino)anthanthrene Derivatives

  摘要：

  A series of 6,12-bis(amino) anthanthrene-based conjugated molecules were prepared and characterized using UV-vis and fluorescence spectroscopy and cyclic voltammetry. The absorption spectra and redox potentials of these molecules can be modulated by changing the conjugated moieties linked at the 4 and 10 positions. Moreover, the optoelectronic properties of these derivatives strongly depend on the moieties attached to the nitrogen atoms at the 6 and 12 positions.

  DOI：

  10.1021/jo402313c
• 作为产物：
  描述：

  2-(trimethylstannyl)thiophene 、 4-溴-2,1,3-苯并噻二唑 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以89%的产率得到4-(thiophen-2-yl)benzo[c][1,2,5]thiadiazole
  参考文献：
  名称：

  Band-Gap Engineering of Donor-Acceptor-Substituted π-Conjugated Polymers

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19980710)4:7<1235::aid-chem1235>3.0.co;2-4

文献信息

• Access to small molecule semiconductors <i>via</i> C–H activation for photovoltaic applications
  作者：Sanchari Shome、Surya Prakhash Singh

  DOI：10.1039/c8cc02706d

  日期：——

  Reporting ruthenium carboxylate-catalysed single step oxidative cross coupling that challenges the conventional Stille and Suzuki coupling reactions, to afford BT and MFBT derivatives.

  报告钌羧酸盐催化的单步氧化交叉偶联，挑战传统的Stille和Suzuki偶联反应，以制备BT和MFBT衍生物。
• Functionalization of the Benzo[c][1,2,5]thiadiazole Scaffold via Mg-, Zn- and Mn-Intermediates
  作者：Paul Knochel、Silvia Zimdars、Heinz Langhals

  DOI：10.1055/s-0030-1259966

  日期：2011.4

  The metalation of all positions of the benzo[c][1,2,5]thiadiazole scaffold using LiCl-solubilized TMP-bases is demonstrated on various substrates. Thus, unsymmetrically substituted benzothiadiazole derivatives and a new fused thiadiazoloindazole have been prepared.

  通过使用LiCl可溶化的TMP基，证明了在不同底物上对苯并[c][1,2,5]噻二唑骨架所有位置进行金属化。因此，已经制备了不对称取代的苯并噻二唑衍生物和一种新的融合噻二唑并吲唑化合物。
• [EN] FLUOROALKYLFLUORENE DERIVATIVES<br/>[FR] DÉRIVÉS FLUOROALKYLFLUORÈNE
  申请人：LOMOX LTD

  公开号：WO2015159098A1

  公开（公告）日：2015-10-22

  There are provided compounds of the formula D-S1-A-S2-B1 wherein A comprises a 2,7- disubstituted 9,9-fluoroalkyl fluorene diradical of the formula wherein S1, S2, D and B1 have meanings given in the description that are useful as charge transport and emissive materials for the fabrication of electronic devices such as diodes, transistors, and photovoltaic devices.

  提供了符合以下公式的化合物 D-S1-A-S2-B1，其中 A 包括公式中的 2,7- 二取代 9,9-氟烷基萘二自由基，其中 S1、S2、D 和 B1 的含义如描述中所述，这些化合物可用作电荷传输和发射材料，用于制造电子器件，如二极管、晶体管和光伏器件。
• Mechano- and Thermo-responsive Luminescence of Crystalline Thienylbenzothiadiazole Derivatives: Stepwise Hypsochromic Switching of Near-Infrared Emission
  作者：Ryohei Yoshida、Takashi Tachikawa、Suguru Ito

  DOI：10.1021/acs.cgd.1c01128

  日期：2022.1.5

  Organic crystals that exhibit mechanochromic luminescence (MCL) switch their emission colors in response to mechanical stimuli, and the original emission colors usually recover upon heating the mechanically changed state. Contrary to the recent enthusiastic investigations of MCL crystals, only a limited number of organic crystals transform to another state showing a third emission color upon sequential exposure to mechanical and thermal stimuli. The development of near-infrared (NIR) emissive organic crystals is another challenge. Although several NIR-emissive crystals that can respond to mechanical stimuli have been developed, further investigations are still required for the multi-stimuli-responsive emission involving the NIR region. In this study, we investigate the mechano-responsive properties of crystalline thienylbenzothiadiazole derivatives. The maximum emission wavelengths of these crystals are observed between blue-green to NIR (502–731 nm), which depend on the substituents R1 and R2 on the thiophene and benzothiadiazole rings, respectively. All derivatives shift the emission wavelength in the hypsochromic direction upon grinding. Moreover, derivatives having a carbonyl group on R2 display further hypsochromic shifts of their emission bands by thermal annealing of the ground states. Specifically, a stepwise hypsochromic shift of the emission from the NIR region has been achieved for a derivative bearing phenyl and formyl groups (R1 = Ph, R2 = CHO). Powder X-ray diffraction analysis, differential scanning calorimetry, and spatially resolved fluorescence microscopy have suggested that the stepwise emission-color switching should be attributed to the crystal-size-dependent luminescence of the carbonyl-substituted derivatives. The present study can be expected to provide useful insights into developing diverse multi-stimuli-responsive luminescent organic crystals and thus accelerate the practical applications of luminescent sensor systems.

  表现出机械致色发光（MCL）的有机晶体响应机械刺激而改变其发射颜色，并且在加热机械改变状态后通常会恢复原始的发射颜色。与最近对 MCL 晶体的热情研究相反，只有有限数量的有机晶体在连续暴露于机械和热刺激时转变为显示第三种发射颜色的另一种状态。近红外（NIR）发射有机晶体的开发是另一个挑战。尽管已经开发出了几种可以响应机械刺激的近红外发射晶体，但涉及近红外区域的多刺激响应发射仍需要进一步研究。在这项研究中，我们研究了结晶噻吩基苯并噻二唑衍生物的机械响应特性。这些晶体的最大发射波长在蓝绿光到近红外光 (502–731 nm) 之间，这分别取决于噻吩环和苯并噻二唑环上的取代基 R1 和 R2。所有衍生物在研磨时都会使发射波长向减色方向移动。此外，R2上具有羰基的衍生物通过基态的热退火显示出其发射带的进一步深色位移。具体来说，带有苯基和甲酰基（R1 = Ph，R2 = CHO）的衍生物已经实现了近红外区域发射的逐步低色位移。粉末X射线衍射分析、差示扫描量热法和空间分辨荧光显微镜表明，逐步发射颜色转换应归因于羰基取代衍生物的晶体尺寸依赖性发光。本研究有望为开发多种多刺激响应发光有机晶体提供有用的见解，从而加速发光传感器系统的实际应用。
• COMPOUNDS WITH TERMINAL HETEROARYLCYANOVINYLENE GROUPS AND THEIR USE IN ORGANIC SOLAR CELLS
  申请人：BASF SE

  公开号：US20160248021A1

  公开（公告）日：2016-08-25

  The present invention relates to a photoactive material comprising a donor substance and an acceptor substance, wherein the donor substance comprises or consists of one or more compounds of formula (I) described herein, or the acceptor substance comprises or consists of one or more compounds of formula (I) described herein, or the donor sub stance comprises or consists of a first compound of formula (I) described herein and the acceptor substance comprises a second compound of formula (I) described herein with the proviso that the first and second compound are not the same, as well as to an organic solar cell comprising said photoactive material. The present invention also relates to a photoelectric conversion device comprising or consisting of two or more organic solar cells comprising said photoactive material and to compounds of formula (I) as described herein for use as donor substance or as acceptor substance in a photoactive material. Further, the present invention relates to the use of a compound of formula (III) as described herein in the synthesis of a compound of formula (I) as described herein.

  本发明涉及一种光活性材料，包括给体物质和受体物质，其中，给体物质包括或由本文所述的一个或多个式(I)化合物组成，或受体物质包括或由本文所述的一个或多个式(I)化合物组成，或给体物质由本文所述的第一种式(I)化合物组成或构成，受体物质由本文所述的第二种式(I)化合物组成，但第一和第二种化合物不相同。此外，本发明还涉及包含该光活性材料的有机太阳能电池，以及由该光活性材料组成的两个或更多有机太阳能电池的光电转换装置。本发明还涉及用于光活性材料中的给体物质或受体物质的式(I)化合物，以及本文所述的式(III)化合物在合成本文所述的式(I)化合物中的使用。