bis(2-naphthylthionyl) disulfide | 61070-95-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: bis(2-naphthylthionyl) disulfide
• 英文别名: Bis(2-thionaphthoyl)disulfid；Naphthalene-2-carbothioylsulfanyl naphthalene-2-carbodithioate
• CAS: 61070-95-9
• 化学式: C₂₂H₁₄S₄
• 分子量: 406.617
• InChiKey: CTNQJAICMHROOP-UHFFFAOYSA-N

物化性质

• 沸点：
  606.8±38.0 °C(Predicted)
• 密度：
  1.391±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  偶氮二异丁腈 、 bis(2-naphthylthionyl) disulfide 以 乙酸乙酯 为溶剂， 以64%的产率得到2-cyanoprop-2-yl 2-naphthyldithiocarboxylate
  参考文献：
  名称：

  Searching for More Effective Agents and Conditions for the RAFT Polymerization of MMA:  Influence of Dithioester Substituents, Solvent, and Temperature

  摘要：

  A series of tertiary dithiobenzoates differently substituted on the phenyl group (Z) were synthesized in order to investigate the RAFT-mediated polymerization of MMA. The chain-transfer agent 2-eyanoprop-2-yl dithiobenzoate, although an excellent RAFT agent for polymerization of MMA, does not yield a very narrow polydispersed polymer at low conversion. The introduction of electron-withdrawing substituents on the dithiobenzoate aromatic ring improves the activity of the chain-transfer agent narrowing the molecular weight distribution, especially in the first 2 h of the process; conversely, electron-donating substituents deteriorate the performance of the process in the early stages. Substituents on the dithiobenzoate that, for reasons of steric hindrance reduce the conjugation of the phenyl with the C=S double bond of the dithiogroup, diminish the effectiveness of the chain-transfer agent. The nature of the leaving group (R) also has a strong influence on the process: the substitution of 2-cyanoprop-2-yl with the bulkier 2-cyano-4-methylpent-2-yl as leaving group improves remarkably the MMA polymerization, especially in the early stages. The solvent effect on MMA RAFT polymerization using benzene, acetonitrile, and DMF was also investigated. The lower propagation rate constant of MMA in benzene gives rise to reduced rates of polymerization but narrower polydispersities of the polymer, especially at low conversions. The RAFT polymerizations of MMA were carried out at 60 and 90 degrees C to assess the temperature dependence of the process. The higher temperature increases both the rate of polymerization and the transfer constant of the RAFT agent, resulting in lower polydispersities at a given conversion. Ab initio calculations confirmed the observed experimental results.

  DOI：

  10.1021/ma0480650
• 作为产物：
  描述：

  二硫化碳 、 2-溴萘 在 碘 、 magnesium 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 生成 bis(2-naphthylthionyl) disulfide
  参考文献：
  名称：

  Searching for More Effective Agents and Conditions for the RAFT Polymerization of MMA:  Influence of Dithioester Substituents, Solvent, and Temperature

  摘要：

  A series of tertiary dithiobenzoates differently substituted on the phenyl group (Z) were synthesized in order to investigate the RAFT-mediated polymerization of MMA. The chain-transfer agent 2-eyanoprop-2-yl dithiobenzoate, although an excellent RAFT agent for polymerization of MMA, does not yield a very narrow polydispersed polymer at low conversion. The introduction of electron-withdrawing substituents on the dithiobenzoate aromatic ring improves the activity of the chain-transfer agent narrowing the molecular weight distribution, especially in the first 2 h of the process; conversely, electron-donating substituents deteriorate the performance of the process in the early stages. Substituents on the dithiobenzoate that, for reasons of steric hindrance reduce the conjugation of the phenyl with the C=S double bond of the dithiogroup, diminish the effectiveness of the chain-transfer agent. The nature of the leaving group (R) also has a strong influence on the process: the substitution of 2-cyanoprop-2-yl with the bulkier 2-cyano-4-methylpent-2-yl as leaving group improves remarkably the MMA polymerization, especially in the early stages. The solvent effect on MMA RAFT polymerization using benzene, acetonitrile, and DMF was also investigated. The lower propagation rate constant of MMA in benzene gives rise to reduced rates of polymerization but narrower polydispersities of the polymer, especially at low conversions. The RAFT polymerizations of MMA were carried out at 60 and 90 degrees C to assess the temperature dependence of the process. The higher temperature increases both the rate of polymerization and the transfer constant of the RAFT agent, resulting in lower polydispersities at a given conversion. Ab initio calculations confirmed the observed experimental results.

  DOI：

  10.1021/ma0480650

文献信息

• RESIST COMPOSITION AND PATTERN-FORMING METHOD USING SAME
  申请人：Kamimura Sou

  公开号：US20080241737A1

  公开（公告）日：2008-10-02

  A resist composition comprises (A) at least two kinds of resins each of which decomposes by the action of an acid to undergo an increase in its solubility for an alkali developer, wherein at least one kind of the resins (A) is a resin synthesized by living radical polymerization using a chain transfer agent represented by formula (I): wherein: A represents an organic group not containing hetero atoms; and Y represents an organic group capable of releasing a radical.

  一种抗蚀性组合物包括（A）至少两种树脂，每种树脂通过酸的作用分解，以增加其对碱性显影剂的溶解度，其中至少一种树脂（A）是通过使用由式（I）表示的链转移剂合成的活性自由基聚合树脂：其中：A代表不含杂原子的有机基团；Y代表能够释放自由基的有机基团。
• Resist composition and pattern-forming method using same
  申请人：FUJIFILM Corporation

  公开号：EP1972641A2

  公开（公告）日：2008-09-24

  A resist composition comprises (A) at least two kinds of resins each of which decomposes by the action of an acid to undergo an increase in its solubility for an alkali developer, wherein at least one kind of the resins (A) is a resin synthesized by living radical polymerization using a chain transfer agent represented by formula (I): wherein: A represents an organic group not containing hetero atoms; and Y represents an organic group capable of releasing a radical.

  一种抗蚀剂组合物包括 (A) 至少两种树脂，每种树脂在酸的作用下分解，对碱显影剂的溶解度增加，其中至少一种树脂 (A) 是使用由式 (I) 表示的链转移剂通过活自由基聚合合成的树脂： 其中 A 代表不含杂原子的有机基团；以及 Y 代表能够释放自由基的有机基团。
• POSITIVE RESIST COMPOSITION AND PATTERN FORMING METHOD
  申请人：Kaneko Yushi

  公开号：US20100104974A1

  公开（公告）日：2010-04-29

  A positive resist composition comprises: (A) a compound that generates an acid upon irradiation with an actinic ray or radiation; and (B) a resin that has an acid-decomposable repeating unit represented by formula (I′), has a dispersity of 1.5 or less and increases its solubility in an alkali developer by action of an acid, wherein Xa 1 represents a hydrogen atom, an alkyl group, a cyano group or a halogen atom; Ry 1 to Ry 3 each independently represents an alkyl group or a cycloalkyl group, and at least two members out of Ry 1 to Ry 3 may combine to form a ring structure; and Z represents a divalent linking group.
• US7695892B2
  申请人：——

  公开号：US7695892B2

  公开（公告）日：2010-04-13