5,10-dibromo-2,7-bis(triisopropylsilyl)naphtho[2,1-b:6,5-b’]dithiophene | 1510834-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,10-dibromo-2,7-bis(triisopropylsilyl)naphtho[2,1-b:6,5-b’]dithiophene
• 英文别名: 5,10-dibromo-2,7-bis(triisopropylsilyl)naphtho[2,1-b:6,5-b']dithiophene；[5,10-Dibromo-2-tri(propan-2-yl)silyl-[1]benzothiolo[5,4-e][1]benzothiol-7-yl]-tri(propan-2-yl)silane；[5,10-dibromo-2-tri(propan-2-yl)silyl-[1]benzothiolo[5,4-e][1]benzothiol-7-yl]-tri(propan-2-yl)silane
• CAS: 1510834-53-3
• 化学式: C₃₂H₄₆Br₂S₂Si₂
• 分子量: 710.828
• InChiKey: BWGKNFDIFPIDQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.57
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,10-dibromo-2,7-bis(triisopropylsilyl)naphtho[2,1-b:6,5-b’]dithiophene 在 四丁基氟化铵 、 9-硼双环[3.3.1]壬烷 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 5,10-didodecylnaphtho[2,1-b:6,5-b’]dithiophene
  参考文献：
  名称：

  Contrasting Effect of Alkylation on the Ordering Structure in Isomeric Naphthodithiophene-Based Polymers

  摘要：

  Semiconducting polymers with alkylated naphtho[1,2-b:5,6-b']dithiophene (NDT3) and naphtho[2,1-b:6,5-b']dithiophene (NDT4) are synthesized and characterized. The solubility of the present polymers is significantly improved as compared to the nonalkylated counterparts with preserving the good charge transport properties. Interestingly, the effect of alkylation is found to be quite distinct between the NDT3 and NDT4 cores. In the NDT3-based polymers, alkylation leads to the more ordered backbone structure and thus the increased crystalline order in the thin film. On the other hand, in the NDT4-based polymers, alkylation is detriment to the backbone ordering, which gives rise to the face-on orientation or amorphous like film structure. This difference can be qualitatively explained by the different alkyl placement; all the neighboring alkyl groups are in the anti arrangement in the NDT3-based polymers, whereas the arrangement is a mixture of anti and syn in the NDT4-based polymers, which likely causes steric impact on the backbone. These observations make us better understood how the alkylation affect the ordering structures, which would be an important guideline for the design of superior semiconducting polymers.

  DOI：

  10.1021/ma402518d
• 作为产物：
  描述：

  5,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,7-bis(triisopropylsilyl)naphtho[2,1-b:6,5-b’]dithiophene 在 copper(ll) bromide 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 水 为溶剂， 反应 15.0h， 以75%的产率得到5,10-dibromo-2,7-bis(triisopropylsilyl)naphtho[2,1-b:6,5-b’]dithiophene
  参考文献：
  名称：

  Contrasting Effect of Alkylation on the Ordering Structure in Isomeric Naphthodithiophene-Based Polymers

  摘要：

  Semiconducting polymers with alkylated naphtho[1,2-b:5,6-b']dithiophene (NDT3) and naphtho[2,1-b:6,5-b']dithiophene (NDT4) are synthesized and characterized. The solubility of the present polymers is significantly improved as compared to the nonalkylated counterparts with preserving the good charge transport properties. Interestingly, the effect of alkylation is found to be quite distinct between the NDT3 and NDT4 cores. In the NDT3-based polymers, alkylation leads to the more ordered backbone structure and thus the increased crystalline order in the thin film. On the other hand, in the NDT4-based polymers, alkylation is detriment to the backbone ordering, which gives rise to the face-on orientation or amorphous like film structure. This difference can be qualitatively explained by the different alkyl placement; all the neighboring alkyl groups are in the anti arrangement in the NDT3-based polymers, whereas the arrangement is a mixture of anti and syn in the NDT4-based polymers, which likely causes steric impact on the backbone. These observations make us better understood how the alkylation affect the ordering structures, which would be an important guideline for the design of superior semiconducting polymers.

  DOI：

  10.1021/ma402518d

文献信息

• Dithiophene-Fused Tetracyanonaphthoquinodimethanes (DT-TNAPs): Synthesis and Characterization of π-Extended Quinoidal Compounds for n-Channel Organic Semiconductor
  作者：Naoyuki Yanai、Takamichi Mori、Shoji Shinamura、Itaru Osaka、Kazuo Takimiya

  DOI：10.1021/ol403234q

  日期：2014.1.3

  Dithiophene-fused tetracyanonaphthoquinodimethanes (DTTNAPs) were synthesized and evaluated as n-channel organic semiconductors. DTTNAPs, regardless of isomeric structures and substituents, have low-lying LUMO energy levels (similar to 4.6 eV below the vacuum level), suitable for stable n-channel field-effect transistors (FETs) under ambient conditions. In fact, alpha-DTTNAP derivatives afforded solution-processed FETs showing an electron mobility of 10(-3) cm(-2) V-1 s(-1), indicating that DTTNAPs are a potential molecular framework for channel organic semiconductors.