5,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,7-dioctylnaphtho[1,2-b:5,6-b']dithiophene | 1398689-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 5,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,7-dioctylnaphtho[1,2-b:5,6-b']dithiophene
• CAS: 1398689-60-5
• 化学式: C₄₂H₆₂B₂O₄S₂
• 分子量: 716.706
• InChiKey: VQSSOPAYSKUXBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.67
• 重原子数：
  50.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,7-dioctylnaphtho[1,2-b:5,6-b']dithiophene 在 sodium hydride 、 copper(I) bromide 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 10.5h， 生成 C₈-α-DTTNAP
  参考文献：
  名称：

  Dithiophene-Fused Tetracyanonaphthoquinodimethanes (DT-TNAPs): Synthesis and Characterization of π-Extended Quinoidal Compounds for n-Channel Organic Semiconductor

  摘要：

  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.

  DOI：

  10.1021/ol403234q
• 作为产物：
  描述：

  2,7-dioctylnaphtho[1,2-b:5,6-b']dithiophene 、 联硼酸频那醇酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 环己烷 为溶剂， 反应 20.0h， 以89%的产率得到5,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,7-dioctylnaphtho[1,2-b:5,6-b']dithiophene
  参考文献：
  名称：

  Orthogonally Functionalized Naphthodithiophenes: Selective Protection and Borylation

  摘要：

  Selective functionalization protocols of naphtho[1,2-b;5,6-b']dithiophene (NDT3) by combining protection of the thiophene alpha-positions and direct borylation on the naphthalene core are described, which allows synthesizing a number of new NDT3-based building blocks with various substituents and isomeric NDT3-based polymers with different main chain structures. The same protocol is applicable to other isomeric naphthodithiophenes (NDTs), which affords a set of key building blocks for the development of elaborated functional pi-materials.

  DOI：

  10.1021/ol301797g