1-(4-bromophenyl)-1,1,1-tris[4-(S-acetylthiomethyl)phenyl]methane | 384820-75-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-(4-bromophenyl)-1,1,1-tris[4-(S-acetylthiomethyl)phenyl]methane
• 英文别名: tris[4-(acetylthiomethyl)phenyl](4-bromophenyl)methane；S-[[4-[bis[4-(acetylsulfanylmethyl)phenyl]-(4-bromophenyl)methyl]phenyl]methyl] ethanethioate
• CAS: 384820-75-1
• 化学式: C₃₄H₃₁BrO₃S₃
• 分子量: 663.72
• InChiKey: ANTJPRKTBZFZDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-1,1,1-tris[4-(S-acetylthiomethyl)phenyl]methane 在 四(三苯基膦)钯 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 35.5h， 生成 Thioacetic acid S-(4-{bis-(4-acetylsulfanylmethyl-phenyl)-[4-(5'''-formyl-3,3'''-dihexyl-[2,2';5',2'';5'',2''']quaterthiophen-5-yl)-phenyl]-methyl}-benzyl) ester
  参考文献：
  名称：

  Large Photocurrent Generation of Gold Electrodes Modified with [60]Fullerene-Linked Oligothiophenes Bearing a Tripodal Rigid Anchor

  摘要：

  [60]Fullerene-linked quarter- and octithiophenes bearing a tripodal rigid anchor have been synthesized as components of highly efficient SAM-based photovoltaic cells. It has been demonstrated that the tripodal anchor plays an important role in preparing a well-organized SAM on a gold electrode, leading to marked enhancement of the photocurrent generation as compared to the reference system with a one-armed anchor.

  DOI：

  10.1021/ja016703d
• 作为产物：
  描述：

  (4-bromophenyl)tris(4-methylphenyl)methane 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 3.5h， 生成 1-(4-bromophenyl)-1,1,1-tris[4-(S-acetylthiomethyl)phenyl]methane
  参考文献：
  名称：

  Large Photocurrent Generation of Gold Electrodes Modified with [60]Fullerene-Linked Oligothiophenes Bearing a Tripodal Rigid Anchor

  摘要：

  [60]Fullerene-linked quarter- and octithiophenes bearing a tripodal rigid anchor have been synthesized as components of highly efficient SAM-based photovoltaic cells. It has been demonstrated that the tripodal anchor plays an important role in preparing a well-organized SAM on a gold electrode, leading to marked enhancement of the photocurrent generation as compared to the reference system with a one-armed anchor.

  DOI：

  10.1021/ja016703d

文献信息

• Diverse Redox-Active Molecules Bearing Identical Thiol-Terminated Tripodal Tethers for Studies of Molecular Information Storage
  作者：Lingyun Wei、Kisari Padmaja、W. Justin Youngblood、Andrey B. Lysenko、Jonathan S. Lindsey、David F. Bocian

  DOI：10.1021/jo0349476

  日期：2004.3.1

  wherein each molecule bears a tether composed of a tripodal linker with three protected thiol groups for surface attachment. The redox-active molecules include ferrocene, zinc porphyrin, ferrocene-zinc porphyrin, magnesium phthalocyanine, and triple-decker lanthanide sandwich coordination compounds. The tripodal tether is based on a tris[4-(S-acetylthiomethyl)phenyl]-derivatized methane. Each redox-active

  为了检查分子结构对自组装单分子层（SAM）中电荷存储的影响，已制备了氧化还原活性分子家族，其中每个分子带有由三脚架连接体组成的系链，该系带具有三个用于表面连接的受保护的硫醇基。氧化还原活性分子包括二茂铁，锌卟啉，二茂铁-锌卟啉，酞菁镁和三层镧系元素夹心配位化合物。三脚架系链基于tris [4-（S-乙酰硫基甲基）苯基]衍生的甲烷。每个氧化还原活性单元通过4,4'-二苯基乙炔单元连接到甲烷顶点。在溶液中和在金上的SAM中检查每种化合物的电化学特性。还对SAM（氧化镁酞菁除外）进行了氧化还原动力学测量，以探测（1）在存在施加电势的情况下电子转移的速度，以及（2）在施加电势为零后的电荷耗散率。断开连接。SAM的电化学研究表明，与具有单个连接位点的系链相比，三脚架系链对Au表面的锚固效果更强。但是，两条系链的电子转移和电荷耗散特性通常是相似的。
• Adsorption Characteristics of Tripodal Thiol-Functionalized Porphyrins on Gold
  作者：Lingyun Wei、Hugo Tiznado、Guangming Liu、Kisari Padmaja、Jonathan S. Lindsey、Francisco Zaera、David F. Bocian

  DOI：10.1021/jp0537005

  日期：2005.12.1

  X-ray photoelectron and Fourier transform infrared spectroscopy studies are reported for self-assembled monolayers (SAMs) of two tripodal thiol-functionalized metalloporphyrins (Zn and Cu) and three benchmark tripods on gold substrates. The tripodal unit common to all five molecules is 1-(phenyl)-1,1,1-tris(4-mercaptomethylphenyl)methane (Tpd). Both porphyrins contain S-acetyl-protected thiols and are linked to the 4-position of the phenyl ring of Tpd via a phenylethyne group. The benchmark molecules include (1) two tripods containing a bromine atom at the 4-position of the apical phenyl ring, one a free thiol and the other its S-acetyl-protected analogue, and (2) a S-acetyl-protected tripod containing a phenylethyne unit at the 4-position of the apical phenyl group. Together, the spectroscopic studies reveal that none of the five tripodal molecules bond to the gold surface via all three sulfur atoms. Instead, the average number of bound thiols ranges from 1.5 to 2, with the porphyrinic molecules generally falling at the middle to upper end of the range and the smallest benchmark tripods falling at the lower end. Similar surface binding is found for the S-acetyl-protected and free benchmark tripods, indicating that the presence of the protecting group does not influence binding. Furthermore, the surface binding characteristics of the SAMs are not sensitive to deposition conditions such as solvent type, deposition time, or temperature of the solution.
• Large Photocurrent Generation of Gold Electrodes Modified with [60]Fullerene-Linked Oligothiophenes Bearing a Tripodal Rigid Anchor
  作者：Daigo Hirayama、Kazuo Takimiya、Yoshio Aso、Tetsuo Otsubo、Taku Hasobe、Hiroko Yamada、Hiroshi Imahori、Shunichi Fukuzumi、Yoshiteru Sakata

  DOI：10.1021/ja016703d

  日期：2002.1.1

  [60]Fullerene-linked quarter- and octithiophenes bearing a tripodal rigid anchor have been synthesized as components of highly efficient SAM-based photovoltaic cells. It has been demonstrated that the tripodal anchor plays an important role in preparing a well-organized SAM on a gold electrode, leading to marked enhancement of the photocurrent generation as compared to the reference system with a one-armed anchor.