dimethyl 2-{5-(4,5-ethylenedithio-1,3-dithiol-2-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-2-ylidene}-1,3-dithiole-4,5-dicarboxylate

• 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: dimethyl 2-{5-(4,5-ethylenedithio-1,3-dithiol-2-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-2-ylidene}-1,3-dithiole-4,5-dicarboxylate
• 英文别名: Dimethyl 2-[5-(5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-2-ylidene]-1,3-dithiole-4,5-dicarboxylate；dimethyl 2-[5-(5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-2-ylidene]-1,3-dithiole-4,5-dicarboxylate
• 化学式: C₁₆H₁₀O₄S₁₀
• 分子量: 586.913
• InChiKey: RUFMBYRXJCJLQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  306
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  4,5-bis(cyanoethylthio)-1,3-dithiole-2-[(4,5-ethylenedithio)-1,3-dithiole-2-ylidene] 在 sodium methylate 、 三甲氧基磷 作用下， 以 甲醇 、 丙酮 、 甲苯 为溶剂， 反应 35.83h， 生成 dimethyl 2-{5-(4,5-ethylenedithio-1,3-dithiol-2-ylidene)-[1,3]dithiolo[4,5-d][1,3]dithiol-2-ylidene}-1,3-dithiole-4,5-dicarboxylate
  参考文献：
  名称：

  Two-Dimensional Brickblock Arrangement in Bis-Fused Tetrathiafulvalene Semiconductors

  摘要：

  Molecular packing arrangement is a very important factor in the charge carrier mobility of organic semiconductors, but its rational design has not been established as yet. Two-dimensional (2D) lamellar packing is an advantageous arrangement for high charge mobility, but few examples have been reported thus far. Herein we show crystal structures and the electronic properties of newly designed bis-fused tetrathiafulvalene (TTF) semiconductors with hetero substituent groups with distinct electronic effects. Unprecedented 2D lamellar alignment is achieved in a single crystal, where the bis-fused TTF rings interact three dimensionally with face-to-face and side-by-side intermolecular S center dot center dot center dot S contacts up to a total of 20 sites per pi molecule and form graphitelike "brickblock" structure. The charge mobility of a single crystal is as high as 0.78 cm(2) V-1 s(-1). Systematic investigations of the semiconductors reveal a key role of intramolecular S center dot center dot center dot O interaction between a bis-fused TTF ring and a methoxycarbonyl group in controlling efficient arrangement, leading to high mobility.

  DOI：

  10.1021/cg401883g

文献信息

• Two-Dimensional Brickblock Arrangement in Bis-Fused Tetrathiafulvalene Semiconductors
  作者：Takeshi Terauchi、Satoshi Sumi、Yuka Kobayashi、Yoshitaka Matsushita、Akira Sato

  DOI：10.1021/cg401883g

  日期：2014.3.5

  Molecular packing arrangement is a very important factor in the charge carrier mobility of organic semiconductors, but its rational design has not been established as yet. Two-dimensional (2D) lamellar packing is an advantageous arrangement for high charge mobility, but few examples have been reported thus far. Herein we show crystal structures and the electronic properties of newly designed bis-fused tetrathiafulvalene (TTF) semiconductors with hetero substituent groups with distinct electronic effects. Unprecedented 2D lamellar alignment is achieved in a single crystal, where the bis-fused TTF rings interact three dimensionally with face-to-face and side-by-side intermolecular S center dot center dot center dot S contacts up to a total of 20 sites per pi molecule and form graphitelike "brickblock" structure. The charge mobility of a single crystal is as high as 0.78 cm(2) V-1 s(-1). Systematic investigations of the semiconductors reveal a key role of intramolecular S center dot center dot center dot O interaction between a bis-fused TTF ring and a methoxycarbonyl group in controlling efficient arrangement, leading to high mobility.