(5-dodecylthiophen-2-yl)trimethylstannane | 1004523-84-5

• 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: (5-dodecylthiophen-2-yl)trimethylstannane
• 英文别名: 5-dodecyl-2-(trimethylstannyl)thiophene；2-trimethylstannyl-5-dodecylthiophene；5-dodecyl-2-trimethylstannylthiophene；(5-dodecylthiophen-2-yl)-trimethylstannane
• CAS: 1004523-84-5
• 化学式: C₁₉H₃₆SSn
• 分子量: 415.271
• InChiKey: TUFUZKJLMCURMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.76
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5-dodecylthiophen-2-yl)trimethylstannane 、 3,6-二溴噻吩[3,2-b]噻吩 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.0h， 以83%的产率得到3,6-bis(5-dodecylthiophen-2-yl)thieno[3,2-b]thiophene
  参考文献：
  名称：

  Biaxially Extended Conjugated Polymers with Thieno[3,2-b]thiophene Building Block for High Performance Field-Effect Transistor Applications

  摘要：

  Biaxially thiophene side chain extended thieno[3,2-b]thiophene (TT2T)-based polymers, PTTT2T, P2TTT2T, PTTTT2T, and PTVTTT2T, were synthesized by Stile coupling polymerization with different conjugated moieties of thiophene (T), bithiophene (2T), thieno[3,2-b]thiophene (TT), and thiophene-vinylene-thiophene (TVT), respectively. The electronic properties of the prepared polymers could be effectively tuned because the variant pi-conjugated building block affected the backbone conformation and the resulted morphology. The morphology of the thin films characterized by atomic force microscopy and grazing incidence X-ray diffraction showed that that P2TTT2T and PTVTTT2T thin films possessed a better molecular packing with a nanofiber structure owing to their coplanar backbone. The average field-effect mobilities of PTTT2T, P2TTT2T, PTTTT2T, and PTVTTT2T were 6.7 x 10(-6), 0.36, 2.2 x 10(-3), and 0.64 cm(2) V-1 s(-1) (maximum 0.71), respectively, attributed to the coplanarity of polymer skeleton. In addition, the fabricated PET devices showed a high on/off ratio over 10(7) under ambient for over 3 months, suggesting the excellent environmental stability. The above results demonstrated that the biaxially extended fused thiophene based conjugated polymers could serve as a potential candidate for organic electronic device applications.

  DOI：

  10.1021/acs.macromol.5b01243
• 作为产物：
  描述：

  溴代十二烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 16.0h， 生成 (5-dodecylthiophen-2-yl)trimethylstannane
  参考文献：
  名称：

  α，ω-二取代茚并[1,2 - b ]芴-6,12-二酮-噻吩分子半导体的设计，合成与表征。通过合成烷基取代基来增强双极性电荷传输†

  摘要：

  设计并合成了一系列在α，ω-位为侧基的带有烃基取代基的茚并[1,2 - b ]芴-6,12-二酮-噻吩衍生物。通过1 H / 13 C NMR，质谱，循环伏安，紫外可见吸收光谱，差示扫描量热法，热重分析和熔点测量，对这些新化合物进行了全面表征。茚并[1,2- b]的固态结构基于单晶X射线衍射（XRD）已经鉴定了]芴-6，12-二酮受体核。还使用密度泛函理论计算研究了结构和电子性能，发现它们与实验结果非常吻合，并提供了进一步的见解。研究了烷基链大小和取向对新型半导体的光电性能，分子间内聚力，薄膜微结构和电荷传输性能的详细影响。两种新的可溶液处理的半导体2EH-TIFDKT和2OD-TIFDKT通过以下方式沉积为薄膜通过X射线衍射（XRD）和原子力显微镜（AFM）研究了固溶剪切，滴铸和液滴固定结晶方法及其形态和微观结构。基于溶液处理的薄膜晶体管2EH-TIFDKT和图20D-TIFDKT显示出与电子和空穴迁移率高达双极设备操作为0

  DOI：

  10.1039/c5ra22359h

文献信息

• Semiconducting Compounds and Related Compositions and Devices
  申请人：Polyera Corporation

  公开号：US20130168659A1

  公开（公告）日：2013-07-04

  Disclosed are new semiconductor materials prepared from thienocoronene-based compounds and related heteroaromatic analogs. Such compounds can exhibit high carrier mobility and/or good current modulation characteristics. In addition, the compounds of the present teachings can possess certain processing advantages such as solution-processability and/or good stability at ambient conditions.

  公开了由基于噻吩冠烯基化合物和相关杂环芳香族类似物制备的新半导体材料。这些化合物可能表现出高载流子迁移率和/或良好的电流调制特性。此外，本教学的化合物可能具有一定的加工优势，如可溶性加工性能和/或在常温条件下的良好稳定性。
• Semiconducting compounds and related compositions and devices
  申请人：Polyera Corporation

  公开号：US08598575B2

  公开（公告）日：2013-12-03

  Disclosed are new semiconductor materials prepared from thienocoronene-based compounds and related heteroaromatic analogs. Such compounds can exhibit high carrier mobility and/or good current modulation characteristics. In addition, the compounds of the present teachings can possess certain processing advantages such as solution-processability and/or good stability at ambient conditions.

  本发明涉及一种由基于噻吩并芘化合物和相关的杂环芳香族类似物制备的新型半导体材料。这些化合物可以表现出高载流子迁移率和/或良好的电流调制特性。此外，本教学的化合物可以具有某些加工优势，例如可溶性加工性和/或在常温下良好的稳定性。
• Influence of Conjugation Axis on the Optical and Electronic Properties of Aryl-Substituted Benzobisoxazoles
  作者：Brian C. Tlach、Aimée L. Tomlinson、Alden G. Ryno、Dawn D. Knoble、Dana L. Drochner、Kyle J. Krager、Malika Jeffries-EL

  DOI：10.1021/jo4007927

  日期：2013.7.5

  Six different 2,6-diethyl-4,8-diarylbenzo[1,2-d:4,5-d']bis(oxazoles) and four different 2,4,6,8-tetraarylbenzobisoxazoles were synthesized in two steps: a Lewis acid catalyzed orthoester cyclization followed by a Suzuki or Stille cross-coupling with various arenes. The influence of aryl group substitution and/or conjugation axis variation on the optical and electronic properties of these benzobis(oxazole) (BBO) compounds was evaluated Structural modifications could be used to alter the HOMO, LUMO, and band gap over a range of 1.0, 0.5, and 0.5 eV, respectively. However, depending on the location and identity of the substituent, the HOMO level Can be altered without significantly impacting the LUMO level. This is supported by the calculated frontier molecular orbitals. Our results indicate that the FMOs and band gaps of benzobisoxazoles can be readily modified either jointly or individually.
• Design, synthesis, and characterization of α,ω-disubstituted indeno[1,2-b]fluorene-6,12-dione-thiophene molecular semiconductors. Enhancement of ambipolar charge transport through synthetic tailoring of alkyl substituents
  作者：Mehmet Ozdemir、Donghee Choi、Guhyun Kwon、Yunus Zorlu、Hyekyoung Kim、Myung-Gil Kim、SungYong Seo、Unal Sen、Murat Citir、Choongik Kim、Hakan Usta

  DOI：10.1039/c5ra22359h

  日期：——

  series of indeno[1,2-b]fluorene-6,12-dione-thiophene derivatives with hydrocarbon substituents at α,ω-positions as side groups have been designed and synthesized. The new compounds were fully characterized by 1H/13C NMR, mass spectrometry, cyclic voltammetry, UV-vis absorption spectroscopy, differential scanning calorimetry, thermogravimetric analysis, and melting point measurements. The solid state structure

  设计并合成了一系列在α，ω-位为侧基的带有烃基取代基的茚并[1,2 - b ]芴-6,12-二酮-噻吩衍生物。通过1 H / 13 C NMR，质谱，循环伏安，紫外可见吸收光谱，差示扫描量热法，热重分析和熔点测量，对这些新化合物进行了全面表征。茚并[1,2- b]的固态结构基于单晶X射线衍射（XRD）已经鉴定了]芴-6，12-二酮受体核。还使用密度泛函理论计算研究了结构和电子性能，发现它们与实验结果非常吻合，并提供了进一步的见解。研究了烷基链大小和取向对新型半导体的光电性能，分子间内聚力，薄膜微结构和电荷传输性能的详细影响。两种新的可溶液处理的半导体2EH-TIFDKT和2OD-TIFDKT通过以下方式沉积为薄膜通过X射线衍射（XRD）和原子力显微镜（AFM）研究了固溶剪切，滴铸和液滴固定结晶方法及其形态和微观结构。基于溶液处理的薄膜晶体管2EH-TIFDKT和图20D-TIFDKT显示出与电子和空穴迁移率高达双极设备操作为0
• Biaxially Extended Conjugated Polymers with Thieno[3,2-<i>b</i>]thiophene Building Block for High Performance Field-Effect Transistor Applications
  作者：Pei-Yin Chao、Hung-Chin Wu、Chien Lu、Chian-Wen Hong、Wen-Chang Chen

  DOI：10.1021/acs.macromol.5b01243

  日期：2015.8.25

  Biaxially thiophene side chain extended thieno[3,2-b]thiophene (TT2T)-based polymers, PTTT2T, P2TTT2T, PTTTT2T, and PTVTTT2T, were synthesized by Stile coupling polymerization with different conjugated moieties of thiophene (T), bithiophene (2T), thieno[3,2-b]thiophene (TT), and thiophene-vinylene-thiophene (TVT), respectively. The electronic properties of the prepared polymers could be effectively tuned because the variant pi-conjugated building block affected the backbone conformation and the resulted morphology. The morphology of the thin films characterized by atomic force microscopy and grazing incidence X-ray diffraction showed that that P2TTT2T and PTVTTT2T thin films possessed a better molecular packing with a nanofiber structure owing to their coplanar backbone. The average field-effect mobilities of PTTT2T, P2TTT2T, PTTTT2T, and PTVTTT2T were 6.7 x 10(-6), 0.36, 2.2 x 10(-3), and 0.64 cm(2) V-1 s(-1) (maximum 0.71), respectively, attributed to the coplanarity of polymer skeleton. In addition, the fabricated PET devices showed a high on/off ratio over 10(7) under ambient for over 3 months, suggesting the excellent environmental stability. The above results demonstrated that the biaxially extended fused thiophene based conjugated polymers could serve as a potential candidate for organic electronic device applications.