5,5'-bis(trimethylstannyl)-2,2'-biselenophene | 220770-51-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 金属芳基
• 英文名称: 5,5'-bis(trimethylstannyl)-2,2'-biselenophene
• 英文别名: 5,5′-bis(trimethylstannyl)-2,2′-biselenophene；trimethyl-[5-(5-trimethylstannylselenophen-2-yl)selenophen-2-yl]stannane
• CAS: 220770-51-4
• 化学式: C₁₄H₂₂Se₂Sn₂
• 分子量: 585.669
• InChiKey: VIHLMKRFDJLTEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  457.0±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5,5'-bis(trimethylstannyl)-2,2'-biselenophene 、 2-bromo-3-dodecylselenophene 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三(邻甲基苯基)磷 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以84%的产率得到5,5'-bis (4-dodecylselenophene-2-yl)-2,2'-biselenophene
  参考文献：
  名称：

  Synthesis and characterization of new selenophene-based conjugated polymers for organic photovoltaic cells

  摘要：

  AbstractThree new polymers poly(3,4′′′‐didodecyl) hexaselenophene) (P6S), poly(5,5′‐bis(4,4′‐didodecyl‐2,2′‐biselenophene‐5‐yl)‐2,2′‐biselenophene) (HHP6S), and poly(5,5′‐bis(3′,4‐didodecyl‐2,2′‐biselenophene‐5‐yl)‐2,2′‐biselenophene) (TTP6S) that have the same selenophene‐based polymer backbone but different side chain patterns were designed and synthesized. The weight‐averaged molecular weights (Mw) of P6S, HHP6S, and TTP6S were found to be 19,100, 24,100, and 19,700 with polydispersity indices of 2.77, 1.48, and 1.41, respectively. The UV–visible absorption maxima of P6S, HHP6S, and TTP6S are at 524, 489, and 513 nm, respectively, in solution and at 569, 517, and 606 nm, respectively, in the film state. The polymers P6S, HHP6S, and TTP6S exhibit low band gaps of 1.74, 1.95, and 1.58 eV, respectively. The field‐effect mobilities of P6S, HHP6S, and TTP6S were measured to be 1.3 × 10−4, 3.9 × 10−6, and 3.2 × 10−4 cm2 V−1 s−1, respectively. A photovoltaic device with a TTP6S/[6,6]‐phenyl C71‐butyric acid methyl ester (1:3, w/w) blend film active layer was found to exhibit an open circuit voltage (VOC) of 0.71 V, a short circuit current (JSC) of 5.72 mA cm−2, a fill factor of 0.41, and a power conversion efficiency (PCE) of 1.67% under AM 1.5 G (100 mW cm−2) illumination. TTP6S has the most planar backbone of the tested polymers, which results in strong π–π interchain interactions and strong aggregation, leading to broad absorption, high mobility, a low band gap, and the highest PCE. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

  DOI：

  10.1002/pola.25064
• 作为产物：
  描述：

  三甲基氯化锡 、 5,5'-dibromo-2,2'-biselenophene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 14.0h， 以65%的产率得到5,5'-bis(trimethylstannyl)-2,2'-biselenophene
  参考文献：
  名称：

  Fluorinated biselenophene-naphthalenediimide copolymers for efficient all-polymer solar cells

  摘要：

  Biselenophene (BS) is generally considered as a promising building block for constructing organic semiconductors, and the 3-positions of selenophene in BS offer a great opportunity for further structural modification. Herein, a novel fluorinated biselenophene, 3,3'-difluoro-2,2'-biselenophene (BSF), was designed and synthesized successfully, and subsequently incorporated into a polymer backbone leading to the resulting polymer PNDIBSF. The polymer backbone planarity was significantly improved via the enhanced intramolecular noncovalent Se center dot center dot center dot F coulombic interactions. Meanwhile, the electronic structure of the polymer was effectively tuned by the high electronegativity of F atoms. All-polymer solar cells (all-PSCs) with J71 and PNDIBSF as polymer donor and acceptor achieved power conversion efficiency (PCE) of 5.20%. In comparsion, all-PSCs based on the non-fluorinated analogue polymer acceptor (PNDIBS) had low PCE of 2.74%. The results demonstrated that BSF is a promising building block for constructing polymer acceptor in all-PSCs, and the fluorination offers a sufficient strategy for further improving performance of selenophene-based polymer semiconductors.

  DOI：

  10.1016/j.dyepig.2020.108721

文献信息

• Synthesis and Structure-Property Correlations of Dicyanovinyl-Substituted Oligoselenophenes and their Application in Organic Solar Cells
  作者：Stefan Haid、Amaresh Mishra、Matthias Weil、Christian Uhrich、Martin Pfeiffer、Peter Bäuerle

  DOI：10.1002/adfm.201201018

  日期：2012.10.23

  are used as donor materials in planar heterojunction (PHJ) and bulk‐heterojunction (BHJ) organic solar cells. The devices show very high fill factors (FF), a high open circuit voltage, and power conversion efficiencies (PCE) of up to 3.4% in PHJ solar cells and slightly reduced PCEs of up to 2.6% in BHJ solar cells. In PHJ devices, the PCE for DCV4S almost doubles compared to the PCE reported for the

  提出了一系列受体-供体-受体（A-D-A）型双麦甲酰基（DCV）取代的寡硒苯酚DCV n S（n = 3-5）的收敛合成。根据共轭骨架的长度，研究了热和光电子性能的趋势。光学测量揭示了红移的吸收光谱，电化学研究表明，与相应的噻吩类似物DCV n相比，DCV n S的最低未占据分子轨道（LUMO）能级降低了T.结果，观察到带隙的降低。四聚体DCV4S的单晶X射线结构分析提供了分子的堆积特征和分子间相互作用的重要见解，进一步证实了DCV受体基团对于分子有序的重要性。DCV4S和DCV5S在平面异质结（PHJ）和体异质结（BHJ）有机太阳能电池中用作施主材料。这些器件在PHJ太阳能电池中显示出非常高的填充因子（FF），高开路电压和高达3.4％的功率转换效率（PCE），而在BHJ太阳能电池中则略微降低了高达2.6％的PCE。在PHJ器件中，用于DCV4S的PCE与报告的低聚噻吩模拟DCV4T的PC
• REGIOREGULAR POLYSELENOPHENES
  申请人：Heeney Martin

  公开号：US20090227764A1

  公开（公告）日：2009-09-10

  The invention relates to regioregular polyselenophenes, to their use as semiconductors or charge transport materials, in optical, electro-optical or electronic devices, and to optical, electro-optical or electronic devices comprising them.

  该发明涉及到具有规则结构的聚硒苯，以及它们作为半导体或电荷传输材料在光学、电光或电子器件中的应用，以及包含它们的光学、电光或电子器件。
• Regioregular polyselenophenes
  申请人：Heeney Martin

  公开号：US08431682B2

  公开（公告）日：2013-04-30

  The invention relates to regioregular polyselenophenes, to their use as semiconductors or charge transport materials, in optical, electro-optical or electronic devices, and to optical, electro-optical or electronic devices comprising them.

  该发明涉及到正规聚硒吲哚的制备，以及它们在半导体或电荷传输材料中的应用，包括光学、电光或电子器件，并且还涉及到包含它们的光学、电光或电子器件。
• 2,5-Bis(2-octyldodecyl)pyrrolo[3,4-<i>c</i>]pyrrole-1,4-(2<i>H</i>,5<i>H</i>)-dione-Based Donor–Acceptor Alternating Copolymer Bearing 5,5′-Di(thiophen-2-yl)-2,2′-biselenophene Exhibiting 1.5 cm²·V^–1·s^–1 Hole Mobility in Thin-Film Transistors
  作者：Jae Seung Ha、Kyung Hwan Kim、Dong Hoon Choi

  DOI：10.1021/ja203189h

  日期：2011.7.13

  A novel diketopyrrolopyrrole-based pi-conjugated copolymer P(DPP-alt-DTBSe), 5, and a known copolymer P(DPP-alt-QT), 4, have been synthesized in 80-90% yield using the Stille coupling reaction. The molecular weights of 4 and 5 are 58 781 and 19 271 g/mol, respectively, with polydispersity values of 3.25-3.35. A relatively small band gap of 1.32-1.39 eV and excellent solubility in organic solvents were achieved in the two polymers. Thin-film transistors made of 5 exhibit outstanding performance (e.g., mu > 1.0-1.5 cm(2).V(-1)s(-1), I-on/I-off > 10(5)-10(6)) with a conventional n-octyltrichlorosilane-SiO2 gate dielectric.
• n-Type Naphthalene Diimide–Biselenophene Copolymer for All-Polymer Bulk Heterojunction Solar Cells
  作者：Ye-Jin Hwang、Guoqiang Ren、Nishit M. Murari、Samson A. Jenekhe

  DOI：10.1021/ma3020239

  日期：2012.11.27

  A new solution processable n-type polymer semiconductor is synthesized and characterized for use as an electron acceptor material in all-polymer bulk heterojunction solar cells. The new crystalline copolymer, poly(naphthalene diimide-alt-biselenophene) (PNDIBS), has a high field-effect electron mobility (0.07 cm(2)/(V s)) and broad visible-near-infrared absorption band with an optical band gap of 1.4 eV. All-polymer bulk heterojunction solar cells comprised of PNDIBS acceptor and poly(3-hexylthiophene) donor have a photovoltaic power conversion efficiency of 0.9%. The external quantum efficiency spectrum of the all-polymer solar cells shows that about 19% of the photocurrent comes from the near infrared (700-900 nm) light harvesting by the new n-type polymer semiconductor.