4-dodecylcarbamoylthiophene-3-carboxylic acid | 847053-25-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 4-dodecylcarbamoylthiophene-3-carboxylic acid
• 英文别名: 4-(dodecylcarbamoyl)thiophene-3-carboxylic acid
• CAS: 847053-25-2
• 化学式: C₁₈H₂₉NO₃S
• 分子量: 339.499
• InChiKey: LWQZLGDVSDTAER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  94.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-dodecylcarbamoylthiophene-3-carboxylic acid 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 硫酸 、 三氟乙酸 作用下， 反应 12.0h， 生成 1,3-二溴-5-十二烷基-4H-噻吩并[3,4-C]吡咯-4,6(5H)-二酮
  参考文献：
  名称：

  强电子接受有机硼构件的二甲烷基化单体：使受体-受体型共轭聚合物用于 n 型热电应用

  摘要：

  受体-受体 (AA) 共聚是开发高性能 n 型共轭聚合物的有效策略。然而，由于合成困难，AA型共轭聚合物的开发具有挑战性。在此，强缺电子双 B←N 桥联联吡啶 (BNBP) 单元的二甲烷基化单体很容易合成，并用于通过 Stille 缩聚开发 AA 型共轭聚合物。所得聚合物显示出 -4.4 eV 的超低 LUMO 能级，这是有机硼聚合物报告的最低值之一。n掺杂后，所得聚合物的电导率为7.8 S cm -1，功率因数为24.8 μW m -1  K -2. 这种性能是 n 型聚合物热电材料中最好的。这些结果证明了 AA 型有机硼聚合物在高性能 n 型热电材料方面的巨大潜力。

  DOI：

  10.1002/anie.202105127
• 作为产物：
  描述：

  3,4-二氰基噻吩 在 氢氧化钾 、 乙酸酐 作用下， 以 乙二醇 、 甲苯 为溶剂， 反应 24.0h， 生成 4-dodecylcarbamoylthiophene-3-carboxylic acid
  参考文献：
  名称：

  New Regiosymmetrical Dioxopyrrolo- and Dihydropyrrolo-Functionalized Polythiophenes

  摘要：

  We present the synthesis of two N-alkylated poly(dioxopyrrolothiophene)s and two N-alkylated poly(dlhydropyrrolothiophene)s with potential application in the field of conducting polymers. The polymers are synthesized from the corresponding 2,5-dibromothiophenes by an Ullmann-type polymerization and a Stille-type polymerization, respectively. The two N-alkylated poly(dihydropyrrolothiophene)s are the first examples of amino-functionalized polythiophenes built from regiosymmetrical thiophene monomers.

  DOI：

  10.1021/ol048659n

文献信息

• DIOXYPYRROLO-HETEROAROMATIC COMPOUNDS AND ORGANIC ELECTRONIC DEVICES USING THE SAME
  申请人：Moon Jae-Min

  公开号：US20100099840A1

  公开（公告）日：2010-04-22

  The present invention relates to dioxypyrrolo-heterocyclic compounds and an organic electronic device using the same. The compound of the present invention satisfies the requirements for use in an organic electronic device such as an organic light emitting device, an organic thin film transistor, and an organic solar cell, for example, suitable energy levels, and the electrochemical and thermal stability, by introducing various substituents to the core structure, and also have amorphous or crystalline property depending on the Mnd of the substituents, to satisfy the characteristics individually required for each of the devices. Further, an organic semi-conductor of p-type or n-type can be fabricated by introducing various substituents to the core structure having a property of n-type, thereby providing stability for the device.

  本发明涉及二氧吡咯杂环化合物及其在有机电子设备中的应用。通过向核心结构引入各种取代基，本发明的化合物满足了用于有机电子设备（如有机发光设备、有机薄膜晶体管和有机太阳能电池）的要求，例如适当的能级以及电化学和热稳定性，并且根据取代基的Mnd具有无定形或结晶性质，以满足各个设备分别需要的特性。此外，通过向具有n型性质的核结构引入各种取代基，可以制造出p型或n型的有机半导体，从而为设备提供稳定性。
• WO2008/127029
  申请人：——

  公开号：——

  公开（公告）日：——
• Thieno[3,4-<i>c</i>]pyrrole-4,6-dione-Based Polymer Semiconductors: Toward High-Performance, Air-Stable Organic Thin-Film Transistors
  作者：Xugang Guo、Rocio Ponce Ortiz、Yan Zheng、Myung-Gil Kim、Shiming Zhang、Yan Hu、Gang Lu、Antonio Facchetti、Tobin J. Marks

  DOI：10.1021/ja205398u

  日期：2011.8.31

  We report a new,p-type semiconducting polymer family based on the thieno[3,4-c]pyrrole-4,6-dione (TPD) building block, which exhibits good processability as well as good mobility and lifetime stability in thin-film transistors (TFTs). TPD homopolymer P1 was synthesized via Yamamoto coupling, whereas copolymers P2-P8 were synthesized via Stile coupling. All of these polymers were characterized by chemical analysis as well as thermal analysis, optical spectroscopy, and cyclic voltammetry. P2-P7 have lower-lying HOMOs than does P3HT by 0.24-0.57 eV, depending on the donor counits, and exhibit large oscillator strengths in the visible region with similar optical band gaps throughout the series (similar to 1.80 eV). The electron-rich character of the dialkoxybithiophene counits in P8 greatly compresses the band gap, resulting in the lowest E-g(opt) in the series (1.66 eV), but also raising the HOMO energy to -5.11 eV. Organic thin-film transistor (OTFT) electrical characterization indicates that device performance is very sensitive to the oligothiophene conjugation length, but also to the solubilizing side chain substituEnts (length, positional pattern). The corresponding thin-film microstructures and morphologies were investigated by XRD and AFM to correlate with the OTFT performance. By strategically varying the oligothiophene donor conjugation length and optimizing the solubilizing side chains, a maximum OTFT hole mobility of similar to 0.6 cm(2) V-1 s(-1) is achieved for P4-based devices. OTFT environmental (storage) and operational (bias) stability in ambient was investigated, and enhanced performance is observed due to the low-lying HOMOs. These results indicate that the TPD is an excellent building block for constructing high-performance polymers for p-type transistor applications due to the excellent processability, substantial hole mobility, and good device stability.
• [EN] DIOXYPYRROLO-HETEROAROMATIC COMPOUNDS AND ORGANIC ELECTRONIC DEVICES USING THE SAME<br/>[FR] COMPOSÉS DIOXYPYRROLO-HÉTÉROAROMATIQUES ET APPAREILS ÉLECTRONIQUES ORGANIQUES LES UTILISANT
  申请人：LG CHEMICAL LTD

  公开号：WO2008127029A1

  公开（公告）日：2008-10-23

  [EN] The present invention relates to dioxypyrrolo-heterocyclic compounds and an organic electronic device using the same. The compound of the present invention satisfies the requirements for use in an organic electronic device such as an organic light emitting device, an organic thin film transistor, and an organic solar cell, for example, suitable energy levels, and the electrochemical and thermal stability, by introducing various substituents to the core structure, and also have amorphous or crystalline property depending on the Mnd of the substituents, to satisfy the characteristics individually required for each of the devices. Further, an organic semi-conductor of p-type or n-type can be fabricated by introducing various substituents to the core structure having a property of n-type, thereby providing stability for the device.
  [FR] La présente invention concerne des composés dioxypyrrolo-hétérocycliques et un appareil électronique organique les utilisant. Le composé selon la présente invention satisfait les exigences d'utilisation dans un appareil électronique organique tel qu'un appareil électroluminescent organique, un transistor à film mince organique et une cellule solaire organique, par exemple des niveaux d'énergie appropriés, et la stabilité électrochimique et thermique, par introduction de divers substituants sur la structure centrale, et présente également des propriétés amorphes ou cristallines selon le Mnd des substituants, afin de satisfaire les caractéristiques individuellement requises pour chacun des appareils. Un semi-conducteur organique de type p ou de type n peut également être fabriqué en introduisant divers substituants sur la structure présentant une propriété de type n centrale, conférant ainsi une stabilité à l'appareil.