5-hexyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione | 566939-54-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-hexyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione
• 英文别名: 5-hexylthieno[3,4-c]pyrrole-4,6-dione
• CAS: 566939-54-6
• 化学式: C₁₂H₁₅NO₂S
• 分子量: 237.323
• InChiKey: JXOXYDPSLHLKLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-hexyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione 在 N-溴代丁二酰亚胺(NBS) 作用下， 生成 1,3-二溴-5-己基-4H-噻吩并[3,4-C]吡咯-4,6(5H)-二酮
  参考文献：
  名称：

  通过基于Thieno [3,4-c]吡咯-4,6-dione的敏化剂中的线性取代基分支，增强了准固态染料敏化太阳能电池的性能

  摘要：

  噻吩并[3,4- c ^ ]吡咯-4,6-二酮基与三苯基胺的有机增感剂（FNE38和FNE40）或久洛尼定（FNE39和FNE41）作为电子给体单元已被设计和合成。线性己基或支链烷基链（2-乙基己基）被掺入染料的分子骨架中，以最大程度地减少分子间的相互作用。然后系统地研究了这些敏化剂的吸收，电化学和光伏性质。发现敏化剂由于其紧密的化学结构而具有相似的光物理和电化学性质，例如吸收光谱和能级。但是，基于两种敏化剂的准固态染料敏化太阳能电池（DSSC）表现出非常不同的性能参数。在己基部分上引入短乙基后，两个开路电压（V oc）和准固态DSSC的短路电流（J sc）。定量研究了源自抑制电荷重组的V oc增益，并与实验观察到的V oc增强非常吻合。因此，增强的太阳能转换效率（η的6.16％），构成增加了23％，则在标准AM达到1.5太阳光，而无需使用coadsorbant剂用于准固态DSSC基于敏F

  DOI：

  10.1002/asia.201200720
• 作为产物：
  描述：

  4-n-hexylcarbamoylthiophene-3-carboxylic acid 在 氯化亚砜 作用下， 反应 3.0h， 以33%的产率得到5-hexyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione
  参考文献：
  名称：

  From Red to Green Luminescence via Surface Functionalization. Effect of 2-(5-Mercaptothien-2-yl)-8-(thien-2-yl)-5-hexylthieno[3,4-c]pyrrole-4,6-dione Ligands on the Photoluminescence of Alloyed Ag–In–Zn–S Nanocrystals

  摘要：

  A semiconducting molecule containing a thiol anchor group, namely 2-(5-mercaptothien-2-yl)-8-(thien-2-yl)-5-hexylthieno[3,4-c]pyrrole-4,6-dione (abbreviated as D-A-D-SH), was designed, synthesized, and used as a ligand in nonstoichiometric quaternary nanocrystals of composition Ag1.0In3.1Zn1.0S4.0(S-6.1) to give an inorganic/organic hybrid. Detailed NMR studies indicate that D-A-D-SH ligands are present in two coordination spheres in the organic part of the hybrid: (i) inner in which the ligand molecules form direct bonds with the nanocrystal surface and (ii) outer in which the ligand molecules do not form direct bonds with the inorganic core. Exchange of the initial ligands (stearic acid and 1-aminooctadecane) for D-A-DSH induces a distinct change of the photoluminescence. Efficient red luminescence of nanocrystals capped with initial ligands (lambda(max) = 720 nm, quantum yield = 67%) is totally quenched and green luminescence characteristic of the ligand appears (lambda(max) = 508 nm, quantum yield = 10%). This change of the photoluminescence mechanism can be clarified by a combination of electrochemical and spectroscopic investigations. It can be demonstrated by cyclic voltammetry that new states appear in the hybrid as a consequence of D-A-D-SH binding to the nanocrystals surface. These states are located below the nanocrystal LUMO and above its HOMO, respectively. They are concurrent to deeper donor and acceptor states governing the red luminescence. As a result, energy transfer from the nanocrystal HOMO and LUMO levels to the ligand states takes place, leading to effective quenching of the red luminescence and appearance of the green one.

  DOI：

  10.1021/acs.inorgchem.0c02468

文献信息

• From-Core and From-End Direct CH Arylations: A Step-Saving New Synthetic Route to Thieno[3,4-<i>c</i>]pyrrole-4,6-dione (TPD)-Incorporated D--π-A-π-D Functional Oligoaryls
  作者：Po-Han Lin、Kuan-Ting Liu、Ching-Yuan Liu

  DOI：10.1002/chem.201501015

  日期：2015.6.8

  contrast to the traditional multistep synthesis, herein an efficient and fewer‐steps new synthetic strategy is demonstrated for the facile preparation of organic‐electronically important D–π–A–π–D‐type oligoaryls through sequential direct CH arylations. This methodology has shown that the synthesis of thieno[3,4‐c]pyrrole‐4,6‐dione (TPD)‐ or furano[3,4‐c]pyrrole‐4,6‐dione (FPD)‐centred target molecules

  与此相反的传统多步合成，本文中的高效和少数步骤新的合成策略是证明了通过顺序直接C中容易制备的有机电子重要d-π-A-π-d型oligoaryls  ħ芳基化。该方法学表明，以噻吩并[3,4- c ]吡咯-4,6-二酮（TPD）或呋喃并[3,4- c ]吡咯-4,6-二酮（FPD）为中心的目标分子的合成可以从核心结构（受体）或末端结构（供体）经济地步入，这为π功能小分子半导体材料的制备提供了更灵活，更简洁的新合成替代品。另外，检查了合成的低聚芳基的光学和电化学性质。
• Pd-catalyzed direct C–H arylation of thieno[3,4-c]pyrrole-4,6-dione (TPD): a step-economical synthetic alternative to access TPD-centred symmetrical small molecules
  作者：Shan-Yun Chang、Po-Han Lin、Ching-Yuan Liu

  DOI：10.1039/c4ra05380j

  日期：——

  to access a series of thieno[3,4-c]pyrrole-4,6-dione (TPD)-based π-conjugated molecules through Pd-catalyzed direct C–H arylations. A comprehensive synthetic study including the screening of various kinds of palladium catalysts, ligands, and bases is reported. Under the optimum reaction conditions, TPD and its common derivatives underwent efficient and mild direct C–H arylations with a variety of functionalized

  我们演示了通过Pd催化的直接C–H芳基化来访问一系列基于噻吩并[3,4- c ]吡咯-4,6-二酮（TPD）的π-共轭分子的分步经济实用的替代方法。据报道，一项综合的综合研究包括对各种钯催化剂，配体和碱的筛选。在最佳反应条件下，TPD及其常见衍生物通过各种官能化的溴代芳烃进行了高效温和的直接C–H芳基化反应。酯，腈，酮，醛和卤化物等官能团具有良好的耐受性，从而大大扩展了反应范围。我们希望所报道的方法将为材料科学家提供一种相对绿色的合成途径，以有效地制备含TPD的π功能材料。
• End-Capping Groups for Small-Molecule Organic Semiconducting Materials: Synthetic Investigation and Photovoltaic Applications through Direct C-H (Hetero)arylation
  作者：Te-Jui Lu、Po-Han Lin、Kun-Mu Lee、Ching-Yuan Liu

  DOI：10.1002/ejoc.201601257

  日期：2017.1.3

  A Pd-catalyzed C–H (hetero)arylation methodology has been optimized for the efficient synthesis of various useful end-capping groups that are widely applied in small-molecule optoelectronic materials. We report herein the synthesis of a broad scope of target molecules ranging from donor-type through acceptor-type to hybrid-type end-capping groups. To demonstrate their application in dye-sensitized

  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%。
• Connecting Direct C−H Arylation Reactions with Dye-Sensitized Solar Cells: A Shortcut to D-A-π-A Organic Dyes
  作者：Po-Han Lin、Te-Jui Lu、Deng-Jhou Cai、Kun-Mu Lee、Ching-Yuan Liu

  DOI：10.1002/cssc.201500993

  日期：2015.10

  developed to target thieno[3,4‐c]pyrrole‐4,6‐dione (TPD)‐based D–A–π–A organic dyes for dye‐sensitized solar cells (DSSCs). Through sequential Pd‐catalyzed direct C−H (hetero)arylation reaction, synthesis of the push–pull‐type small molecules is reduced from the traditional six steps to two steps. In this report, we focus on the optimization of the key C−H monoarylation of TPD by screening ligands

  开发了一种分步经济的合成策略，以针对噻吩[3,4– c ]吡咯-4,6-二酮（TPD）的D–A–π–A有机染料为染料敏化太阳能电池（DSSC）。通过顺序的Pd催化的直接C（杂）芳基化反应，推挽式小分子的合成从传统的六个步骤减少到了两个步骤。在本报告中，我们专注于通过筛选配体，酸添加剂，碱和溶剂来优化TPD的关键CH单芳基化。该反应证明对具有多种不同供体基团的新型D–A–π–A有机染料具有通用性，并且可以在最佳反应条件下有效制备几种衍生物。敏感的醛官能度是转化为TiO 2的锚定基团所需的中间体耐受性良好。根据我们的综合研究，使用两种设计的敏化剂对DSSC进行了制造和表征。器件的光伏特性提供了0.60–0.69 V的开路电压，10.85–11.07 mA cm -2的短路电流密度和69.9–70.8％的填充系数，这相当于总的功率转换效率为4.61–5.33％。
• Push–pull thiophene-based small molecules with donor and acceptor units of varying strength for photovoltaic application: beyond P3HT and PCBM
  作者：Martina Marinelli、Andrea Candini、Filippo Monti、Alex Boschi、Mattia Zangoli、Elisabetta Salatelli、Filippo Pierini、Massimiliano Lanzi、Alberto Zanelli、Massimo Gazzano、Francesca Di Maria

  DOI：10.1039/d1tc02641k

  日期：——

  Here is reported an expedient synthesis implementing enabling technologies of a family of thiophene-based heptamers alternating electron donor (D) and acceptor (A) units in a D–A′–D–A–D–A′–D sequence. The nature of the peripheral A groups (benzothiadiazole vs. thienopyrrole-dione vs. thiophene-S,S-dioxide) and the strength of the donor units (alkyl vs. thioalkyl substituted thiophene ring) have been

  这里报道了一种权宜的合成，实施了基于噻吩的七聚体家族在 D-A'-D-A-D-A'-D 序列中交替电子供体 (D) 和受体 (A) 单元的使能技术。外围 A 基团的性质（苯并噻二唑vs.噻吩并吡咯二酮vs.噻吩-S、S-二氧化物）和供体单元的强度（烷基vs.硫代烷基取代的噻吩环）已被改变以微调 D-A 低聚物的化学物理性质，以影响固态的堆积排列以及提高光伏性能。已经通过光谱学、电化学和密度泛函理论计算研究了所有化合物的光电特性。电化学测量和开尔文探针力显微镜 (KPFM) 预测了这些低聚物的双功能行为，表明当与 PCBM 混合时可以将它们用作供体材料，并在与 P3HT 结合时用作受体材料。对其光伏特性的研究证实了这种不寻常的特性，并且表明可以通过不同的替代模式来调整性能。此外，