4,7-di(thiophen-2-yl)benzo[c][1,2,5]-selenadiazole | 711026-55-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4,7-di(thiophen-2-yl)benzo[c][1,2,5]-selenadiazole
• 英文别名: 4,7-di(thiophen-2-yl)benzo[c][2,1,3]selenadiazole；4,7-di(2-thienyl)benzo[2,1,3]thiadiazole；4,7-di-2-thienyl-2,1,3-benzoselenadiazole；4,7-bis(2-thienyl)-2,1,3-benzoselenadiazole；4,7-Di(thiophen-2-yl)benzo[c][1,2,5]selenadiazole；4,7-dithiophen-2-yl-2,1,3-benzoselenadiazole
• CAS: 711026-55-0
• 化学式: C₁₄H₈N₂S₂Se
• 分子量: 347.323
• InChiKey: FPCWDJTVMDFDNK-UHFFFAOYSA-N

物化性质

• 沸点：
  512.4±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• 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：

  4,7-di(thiophen-2-yl)benzo[c][1,2,5]-selenadiazole 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以54%的产率得到4,7-双(5-溴-2-噻吩基)-2,1,3-苯并硒二唑
  参考文献：
  名称：

  基于具有大斯托克斯位移的苯并二异恶唑染料的高效发光太阳能聚光器。

  摘要：

  合成了具有电子给体（D）和受体（A）部分的五个扩展π共轭体系。它们的基本D‐A‐D结构基序是苯并噻二唑单元，对称地配有两个噻吩环（S2T）。其变体包括1）相同的分子框架，其中硫被硒（Se2T）取代，还被四个噻吩单元（Se4T）和2）D'-D-A-D系统在一个位置具有N-咔唑供体部分末端（CS2TCHO）和D'-D-A-D-A'阵列，另一末端带有另一个受体羰基单元（CS2TCHO）。目标是利用用于发光太阳能聚光器（LSC）的五个分子的强发光特性和较大的斯托克斯位移。它们全都在低至630 nm的UV / Vis区域显示出强烈的吸收光谱，这已通过DFT完全合理化。已在CH 2 Cl 2中研究了发射特性（298和77 K）以及在PMMA和PDMS矩阵中，可测量光致发光量子产率（高达98％）和其他关键光学参数。染料-PMMA系统在光学和外部量子效率（分别为OQE = 47.6％和EQE = 31.3％）和通量增益（F

  DOI：

  10.1002/chem.202001210
• 作为产物：
  描述：

  3,6-二溴-1,2-苯二胺 在 selenium(IV) oxide 、 三丁基氯化锡 、 lithium bromide 作用下， 生成 4,7-di(thiophen-2-yl)benzo[c][1,2,5]-selenadiazole
  参考文献：
  名称：

  Novel conjugated alternating copolymer based on 2,7-carbazole and 2,1,3-benzoselenadiazole

  摘要：

  A novel conjugated alternating copolymer (PCzDBSe) based on N-9'-heptadecanyl-2,7-carbazole and 5,5(4',7'-di-2-thienyl-2',1',3'-benzoselenadiazole) was synthesized by Suzuki polycondensation. The polymer reveals excellent thermal stabilities with the decomposition temperature (5% weight loss) of 390 degrees C and the glass-transition temperature of 140 degrees C. The absorption peaks of the polymer are located at 412 and 626 nm, respectively, while the absorption onset is extended to 716 nm, which is 56 nm red-shifted as compared with its analogue, poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5-(4',7'-di-2-thienyl-2',1',3'-benzothiadiazole)] (PCDTBT). The HOMO and LUMO levels of the polymer were estimated to be -5.28 and -3.55 eV, respectively, with an optical bandgap of 1.73 eV. The hole mobility of PCzDBSe as deduced from a solution-processed organic field effect transistor (OFET) was found to be 3.9 x 10(-4) cm(2) V-1 s(-1). Polymer solar cells (PSCs) based on the blends of PCzDBSe and [6,6]-phenyl-C-71-butyric acid methyl ester (PC71BM) with a weight ratio of 1:4 were fabricated. Under AM 1.5 (AM, air mass), 100 mW cm(-2) illumination, the devices were found to have an open-circuit (V-OC) of 0.75 V, a short-circuit current density (J(sc)) of 7.23 mA cm(-2), a fill factor (FF) of 45% and a power conversion efficiency (PCE) of 2.58%. The primary results indicate that 5,5-(4',7'-di-2-thienyl-2',1',3'-benzoselenadiazole) is a promising unit for low bandgap polymer for polymer solar cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2010.04.057

文献信息

• Structural Design Principle of Small-Molecule Organic Semiconductors for Metal-Free, Visible-Light-Promoted Photocatalysis
  作者：Lei Wang、Wei Huang、Run Li、Dominik Gehrig、Paul W. M. Blom、Katharina Landfester、Kai A. I. Zhang

  DOI：10.1002/anie.201603789

  日期：2016.8.8

  on the structural design principle of small‐molecule organic semiconductors as metal‐free, pure organic and visible light‐active photocatalysts. Two series of electron‐donor and acceptor‐type organic semiconductor molecules were synthesized to meet crucial requirements, such as 1) absorption range in the visible region, 2) sufficient photoredox potential, and 3) long lifetime of photogenerated excitons

  在此，我们报告了小分子有机半导体作为无金属，纯有机和可见光活性光催化剂的结构设计原理。合成了两个系列的电子给体和受体型有机半导体分子以满足关键要求，例如1）可见光区域的吸收范围，2）足够的光氧化还原电势和3）光生激子的寿命长。在富含丙二酸酯衍生物的富电子杂芳族化合物的分子间CH官能化中证明了光催化活性。描述了光诱导电子在有机光催化剂，底物和牺牲剂之间传输的机理。凭借其可调的吸收范围和定义的能带结构，
• Synthesis and Characterization of Conjugated Polymers Based on Benzoselenadiazole
  作者：Xiaoxia Sun、Xiaolong Lei、Yu Hu

  DOI：10.14233/ajchem.2015.17885

  日期：——

  A multistep synthesis of the electron-poor 4,7-di(thiophen-2-yl)benzo[c][1,2,5]selenadiazole are presented. The new deficient acceptor has good solubility in organic solvents to permit an appropriate coating process. P1 was synthesized by direct oxidative polymerization under the reaction condition with FeCl3 and CH3NO2. The spectra of polymers P1 to P2 show homogenous absorptions across most of the visible spectrum (450-650 nm). Solutions of P1 show a dark purple-black colour due to the lack of absorption in the far blue and red regions. And the solution of P2 exhibits a bright orange-red colour due to the increased reflection/transmission of red light. Both of the polymers were characterized by IR, UV-visible and cyclic voltammetry.

  本文介绍了缺电子的4,7-双(噻吩-2-基)苯并[c][1,2,5]硒二唑的多步合成过程。这种新型缺电子受体在有机溶剂中具有良好的溶解性，从而允许适当的涂层加工。P1是通过在FeCl3和CH3NO2的反应条件下直接氧化聚合合成的。P1至P2的光谱显示在整个可见光谱（450-650 nm）范围内具有均匀吸收。P1溶液呈现深紫黑色，因为其在远蓝光和红光区域的吸收较弱。而P2溶液呈现出鲜亮的橙红色，这是由于其对红光的反射/透射增强。两种聚合物均通过红外光谱、紫外-可见光谱和循环伏安法进行了表征。
• Benzochalcogendiazole-based conjugated molecules: investigating the effects of substituents and heteroatom juggling
  作者：Heta A. Patel、Viraj J. Bhanvadia、Hemant M. Mande、Sanjio S. Zade、Arun L. Patel

  DOI：10.1039/c9ob01762c

  日期：——

  photophysical properties of the synthesized benzochalcogendiazole-based small molecules, having different terminal substituents, have been compared. Moreover, the structural aspects, including the packing patterns and non-bonding interactions of the conjugated molecules, have been investigated using the single crystal X-ray diffraction (SCXRD) technique.

  使用聚苯胺（PANI）固定的钯作为非均相催化剂，已经获得了一种方便有效的基于苯并硫属元素二唑的小分子合成方法。已经比较了具有不同末端取代基的合成的苯并硫属元素二唑基小分子的光物理性质。此外，已经使用单晶X射线衍射（SCXRD）技术研究了包括共轭分子的堆积模式和非键相互作用在内的结构方面。
• Synthesis and characterization of cyclopentadithiophene-based low bandgap copolymers containing electron-deficient benzoselenadiazole derivatives for photovoltaic devices
  作者：In Hwan Jung、Hoyeon Kim、Moo-Jin Park、Bongjun Kim、Jong-Hwa Park、Eunjae Jeong、Han Young Woo、Seunghyup Yoo、Hong-Ku Shim

  DOI：10.1002/pola.23910

  日期：2010.3.15

  synthesized two cyclopentadithiophene (CDT)‐based low bandgap copolymers, poly[(4,4‐bis(2‐ethyl‐hexyl)‐4H‐cyclopenta[2,1‐b:3,4‐b′]dithiophene‐2,6‐diyl)‐alt‐(benzo[c][1,2,5]selenadiazole‐4,7‐diyl)] (PCBSe) and poly[(4,4‐bis(2‐ethyl‐hexyl)‐4H‐cyclopenta[2,1‐b:3,4‐b′]dithiophene‐2,6‐diyl)‐alt‐(4,7‐dithiophen‐2‐yl‐benzo[c][1,2,5]selenadiazole‐5,5′‐diyl)] (PCT2BSe), for use in photovoltaic applications. Through

  我们合成了两种基于环戊二噻吩（CDT）的低带隙共聚物，聚[（4,4-双（2-乙基-己基）-4 H-环戊基[2,1- b：3,4- b ']二噻吩-2,6-二基） - ALT - （苯并[ c ^ ] [1,2,5] selenadiazole -4,7-二基）]（PCBSe）和聚[（4,4-双（2-乙基-己基） - 4 H-环戊[2,1- b：3,4- b ']二噻吩-2,6-二基）-alt-（4,7-二噻吩-2-基-苯并[ c] [1,2,5]硒代二唑-5,5'-二基]]（PCT2BSe），用于光伏应用。通过给电子的CDT单元和受电子的苯并硒二唑之间的内部电荷转移相互作用，我们实现了带隙为1.37–1.46 eV的超低带隙聚合物。由于PCT2BSe骨架的电子供体-受体（D-A）结构扭曲，因此PCT2BSe的最大紫外可见吸收比PCBSe经历了更大的蓝移。这些结果得到了从头算起D–A复合物的
• Synthesis of benzoselenadiazole-based small molecule and phenylenevinylene copolymer and their application for efficient bulk heterojunction solar cells
  作者：John A. Mikroyannidis、P. Suresh、G.D. Sharma

  DOI：10.1016/j.orgel.2009.11.010

  日期：2010.2

  A new low-band gap small molecule (Se-SM), which contains dithyenyl-benzoselenadiazole as central unit and terminal cyanovinylene 4-nitrophenyls, was synthesized. In addition, a new phenylenevinylene copolymer (P) containing dithyenyl-dinitrobenzothiadiazole moieties was synthesized by Heck coupling. Se-SM showed broad absorption band with long-wavelength absorption maximum (lambda(a,max)) at similar to 640 nm and optical band gap (E-g(opt)) of 1.67 eV. Copolymer P had lambda(a,max) around 420 nm and E-g(opt) of 2.31 eV. The dark current-voltage characteristics and incident photon to current efficiency spectra of the devices based on copolymer P and Se-SM indicates that both materials behave as p-type organic semiconductors. The power conversion efficiency (PCE) of the photovoltaic devices based on these materials is low. However, the PCE of the devices fabricated with the blends of copolymer P or Se-SM with PCBM, was improved significantly. The increase is attributed to the formation of bulk heterojunction with increased interfacial area. The effect of the incorporation of Se-SM molecule on the photovoltaic properties of copolymer P: PCBM blend has been also investigated. The overall PCE of the copolymer P: PCBM: Se-SM device is approximately 2.24%, which is further enhanced up to 3.16%, when the thermally annealed blend is used. Therefore, we conclude that the Se-SM molecule increases the light harvesting property of the blend and also provides efficient path for holes and electron in copolymer and PCBM phases, respectively. (C) 2009 Elsevier B.V. All rights reserved.