4-(2,3-二氢噻吩并[3,4-b]-1,4-二噁英-5-基)-苯甲醛 | 861648-73-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(2,3-二氢噻吩并[3,4-b]-1,4-二噁英-5-基)-苯甲醛
• 中文别名: 4-(2,3-二氢噻吩并[3,4-B]-1,4-二噁英-5-基)-苯甲醛
• 英文名称: 4‑(2,3‑dihydrothieno[3,4‑b][1,4]dioxin‑5‑yl)benzaldehyde
• 英文别名: 4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-benzaldehyde；4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)benzaldehyde；4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl)benzaldehyde；4-(3,4-ethylenedioxythiophen-2-yl)benzaldehyde
• CAS: 861648-73-9
• 化学式: C₁₃H₁₀O₃S
• 分子量: 246.287
• InChiKey: QLNYREQMBWRUEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2,3-二氢噻吩并[3,4-b]-1,4-二噁英-5-基)-苯甲醛 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 4-(7-(4-(diphenylamino)phenyl)-2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)benzaldehyde
  参考文献：
  名称：

  Donor–acceptor dyes with fluorine substituted phenylene spacer for dye-sensitized solar cells

  摘要：

  一系列新的有机敏化剂LJB-H、LJB-Fo和LJB-Fm分别以三苯胺、3,4-乙烯二氧噻吩加各种官能化亚苯基和氰基丙烯酸作为供体、β-间隔基和锚定基团。这些有机敏化剂表现出比母体 LJ1 染料高得多的摩尔消光系数，并显示出显着的氟取代基效应。在相对于氰基丙烯酸的间位具有氟取代的LJB-Fm具有较低的S0-S1间隙和与TiO2电极较弱的耦合（参见LJB-H和LJB-Fo）。相反，由于与氰基丙烯酸的共振效应，邻位F取代的LJB-Fo具有更大的能隙，但与TiO2的亲和力更强。结果，LJB-Fo 显示出更好的 DSSC 性能，Jsc = 15.58 mA cm±2，Voc = 787 mV，FF = 0.67 且 δ = 8.22%。

  DOI：

  10.1039/c0jm02433c
• 作为产物：
  描述：

  对溴苯甲醛 、 3,4-乙烯二氧噻吩 在 palladium diacetate 、 potassium carbonate 、 正丁基二(1-金刚烷基)膦 、 三甲基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以61%的产率得到4-(2,3-二氢噻吩并[3,4-b]-1,4-二噁英-5-基)-苯甲醛
  参考文献：
  名称：

  小分子有机半导体材料的封端基团：通过直接 CH（杂）芳基化的合成研究和光伏应用

  摘要：

  Pd催化的C-H（杂）芳基化方法已被优化用于有效合成广泛应用于小分子光电材料的各种有用的封端基团。我们在此报告了范围广泛的目标分子的合成，范围从供体型到受体型到混合型封端基团。为了证明它们在染料敏化太阳能电池中的应用，我们设计了两种新的 D-A-π-A' 型有机敏化剂（CYL-3 和 CYL-4），它们是通过连续 C -H 芳基化使用容易获得的封端基团。基于 CYL-3 和 CYL-4 的器件的 Voc 值为 0.67–0.71 V，Jsc 值为 10.07–11.63 mA cm–2，FF 值为 70.6–72.9 %，对应的总功率转换效率为 4.76– 6.02%。

  DOI：

  10.1002/ejoc.201601257

文献信息

• Efficient synthesis of mono- and bis-arylated ethylenedioxy thiophene-based functional π-conjugated molecules via clay-supported palladium-catalysed direct arylation reactions
  作者：Sneha Sreekumar、Soumya Xavier、Avudaiappan Govindan、Raihamol Erattammottil Thampikannu、Kannan Vellayan、Beatriz González

  DOI：10.1007/s11164-020-04219-3

  日期：2020.10

  active Pd catalyst was prepared by the modification of montmorillonite clay. The catalyst was found to be effective for the synthesis of ethylenedioxy thiophene-based π-conjugated molecules. The reaction proceeded through clay-supported Pd-catalysed direct C–H bond activation (arylation) mechanism. Preparation, characterization and application of the catalysts are reported. The products were analysed with

  通过改性蒙脱土制备了活性钯催化剂。发现该催化剂对于合成基于乙二氧基噻吩的π-共轭分子是有效的。该反应通过粘土负载的Pd催化的直接C–H键活化（芳基化）机理进行。报告了催化剂的制备，表征和应用。用LCMS分析产物，并与报道的光谱数据（FT-IR，1 H NMR）进行比较。在三个反应周期中测试了粘土负载的钯催化剂对直接芳基化反应的可重复使用性，而没有明显降低催化活性。
• Synthesis of mono- and bis-arylated 3,4-(ethylenedioxythiophenes) via direct palladium catalyzed arylation reactions
  作者：Arasambattu K. Mohanakrishnan、P. Amaladass、J. Arul Clement

  DOI：10.1016/j.tetlet.2006.11.138

  日期：2007.1

  The synthesis of arylated/heteroarylated 3,4-ethylenedioxythiophene derivatives is reported using a straightforward palladium mediated Heck coupling of 3,4-ethylenedioxythiophene with various aryl/heteroaryl halides. (c) 2006 Elsevier Ltd. All rights reserved.
• Pd-mediated C–H arylation of EDOT and synthesis of push–pull systems incorporating EDOT
  作者：P. Amaladass、J. Arul Clement、Arasambattu K. Mohanakrishnan

  DOI：10.1016/j.tet.2007.07.037

  日期：2007.10

  The direct C-H arylation of 3,4-ethylenedioxythiophene (EDOT) is described under Heck-type experimental conditions. This methodology has been used to synthesize a series of push-pull systems containing EDOT units. (C) 2007 Elsevier Ltd. All rights reserved.
• The structural modification of thiophene-linked porphyrin sensitizers for dye-sensitized solar cells
  作者：Na Xiang、Xianwei Huang、Xiaoming Feng、Yijiang Liu、Bin Zhao、Lijun Deng、Ping Shen、Junjie Fei、Songting Tan

  DOI：10.1016/j.dyepig.2010.05.003

  日期：2011.1

  Three donor (pi-spacer) acceptor porphyrin dyes were synthesized for use in dye-sensitized solar cells The dyes comprised the same donor (porphyrin derivative) and acceptor/anchoring group (2-cyanoacrylic acid) but varying pi-spacer consisting of a combination of 4-methylthiophene, 4-hexylthiophene or 3,4-ethylenedioxythiophene groups The dyes displayed different adsorption behavior and coverage of the TiO2 surface (C) 2010 Elsevier Ltd. All rights reserved
• Sn- and Pd-Free Synthesis of D-π-A Organic Sensitizers for Dye-Sensitized Solar Cells by Cu-Catalyzed Direct Arylation
  作者：Jiung-Huai Huang、Po-Han Lin、Wei-Ming Li、Kun-Mu Lee、Ching-Yuan Liu

  DOI：10.1002/cssc.201700421

  日期：2017.5.22

  Abstract<A variety of D–π–A‐type functional organic dyes are facilely synthesized by direct C−H arylation catalyzed by inexpensive copper salts. Under optimized reaction conditions, a broad substrate scope with good functional group compatibility was demonstrated. Based on this synthetic strategy, three new dye sensitizers (CYL‐5–7) were designed and fabricated for use in dye‐sensitized solar cells (DSSCs). Photovoltaic characterization showed that these devices gave open‐circuit voltages of 0.65–0.75 V, short‐circuit currents of 5.90–12.60 mA cm−2, and fill factors of 65.6–76.9 %, corresponding to power conversion efficiencies (PCEs) of 2.95–6.20 %. This work represents the first use of Cu‐catalyzed C−H arylation for a step‐saving, Sn‐free synthesis of precursor dyes for DSSC applications.