5,6-di(propylsulfonyl)-1,3-diiminoisoindoline | 1009573-87-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 5,6-di(propylsulfonyl)-1,3-diiminoisoindoline
• 英文别名: 4,5-dipropylsulfonyldiiminoisoindoline
• CAS: 1009573-87-8
• 化学式: C₁₄H₁₉N₃O₄S₂
• 分子量: 357.455
• InChiKey: GPTXQAGPFLXVMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  128.01
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5,6-di(propylsulfonyl)-1,3-diiminoisoindoline 在 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 反应 12.0h， 以32%的产率得到
  参考文献：
  名称：

  Stabilization of Charge-Separated States in Phthalocyanine−Fullerene Ensembles through Supramolecular Donor−Acceptor Interactions

  摘要：

  A novel ZnPC-C-60 dyad (3), in which two photoactive units are brought together by a phenylenevinylene spacer has been synthesized. The synthetic strategy en route toward 3 involves a Heck reaction to attach 4-vinylbenzaldehyde to a monoioclophthalocyanine precursor, followed by standard cycloaddition of azomethine ylides (generated from the formylPc derivative and N-methylglycine) to one of the double bonds of C-60. Electrochemical studies reveal that in 3 the ZnPc is about 39 mV more difficult to oxidize than in the corresponding ZnPc, reference, which points to appreciable electronic communication between ZnPc and C-60 in the ground state. In the excited state, photoexcitation leads to the formation of a charge-separated ZnPC.+-C-60(.-) state, for which a lifetime of 130 ns was determined in THF. Hetero-association between complementary PCs (1 and 2 or 3 and 2), which carry different peripheral functionalities (i.e., either electron-donating alkoxy groups or electron-deficient alkylsulfonyl chains) was assessed by different techniques. They provided evidence for donor-acceptor 1:1 complex formation with a stability constant of ca. 10(5) M-1 in CHCl3. Interestingly, hetero-association of ZnPC-C-60 dyad 3 with an electrondeficient PdPc (2) allowed the construction of supramolecular triads, in which a substantial stabilization of the radical pair is seen relative to that of the covalently linked dyad ZnPC-C-60 (3).

  DOI：

  10.1021/ja058123c
• 作为产物：
  描述：

  4,5-bis(propylsulfonyl)phthalonitrile 在 氨 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以45%的产率得到5,6-di(propylsulfonyl)-1,3-diiminoisoindoline
  参考文献：
  名称：

  液晶中酞菁-[60]富勒烯二元的自组织

  摘要：

  使用其中液晶元将介晶性诱导为非介晶化合物的共混物，使得酞菁-[60]富勒烯（Pc-C 60）二元化合物自组织成液晶成为可能。PC-C 60个成对层1，2，或3，其中两个光活性单元由亚苯基亚乙烯基间隔件放在一起时，已通过Heck反应合成的链接4-乙烯基苯甲醛到monoiodophthalocyanine前体，然后通过甲亚胺叶立德的标准环加成产生从甲酰基Pc衍生物和N-甲基甘氨酸到C 60的双键之一。通过形成不同的混合物的介晶性质和热性质的液晶性酞菁4和成对层1，2，或3使用偏光显微镜（POM），差示扫描量热法（DSC），和X射线衍射（XRD）进行了研究。共混物的DSC图显示从晶态到中间相的清晰过渡，并且从粉末衍射实验获得的测量结构参数与盘状六方柱状（Col h）结构一致。考虑到在Pc-C 60 dyad和酞菁4的分离分子域中的偏析由于柱直径的不匹配和纯二元体缺乏介晶特性而将导致同构现象的发生

  DOI：

  10.1021/jo7022763

文献信息

• Stabilization of Charge-Separated States in Phthalocyanine−Fullerene Ensembles through Supramolecular Donor−Acceptor Interactions
  作者：Andrés de la Escosura、M. Victoria Martínez-Díaz、Dirk M. Guldi、Tomás Torres

  DOI：10.1021/ja058123c

  日期：2006.3.1

  A novel ZnPC-C-60 dyad (3), in which two photoactive units are brought together by a phenylenevinylene spacer has been synthesized. The synthetic strategy en route toward 3 involves a Heck reaction to attach 4-vinylbenzaldehyde to a monoioclophthalocyanine precursor, followed by standard cycloaddition of azomethine ylides (generated from the formylPc derivative and N-methylglycine) to one of the double bonds of C-60. Electrochemical studies reveal that in 3 the ZnPc is about 39 mV more difficult to oxidize than in the corresponding ZnPc, reference, which points to appreciable electronic communication between ZnPc and C-60 in the ground state. In the excited state, photoexcitation leads to the formation of a charge-separated ZnPC.+-C-60(.-) state, for which a lifetime of 130 ns was determined in THF. Hetero-association between complementary PCs (1 and 2 or 3 and 2), which carry different peripheral functionalities (i.e., either electron-donating alkoxy groups or electron-deficient alkylsulfonyl chains) was assessed by different techniques. They provided evidence for donor-acceptor 1:1 complex formation with a stability constant of ca. 10(5) M-1 in CHCl3. Interestingly, hetero-association of ZnPC-C-60 dyad 3 with an electrondeficient PdPc (2) allowed the construction of supramolecular triads, in which a substantial stabilization of the radical pair is seen relative to that of the covalently linked dyad ZnPC-C-60 (3).
• Self-Organization of Phthalocyanine−[60]Fullerene Dyads in Liquid Crystals
  作者：Andrés de la Escosura、M. Victoria Martínez-Díaz、Joaquín Barberá、Tomás Torres

  DOI：10.1021/jo7022763

  日期：2008.2.1

  The use of blends in which a mesogen induces mesomorphism into a non-mesogenic compound has made possible the self-organization of phthalocyanine−[60]fullerene (Pc-C60) dyads into liquid crystals. Pc-C60 dyads 1, 2, or 3, in which two photoactive units are brought together by a phenylenevinylene spacer, have been synthesized through a Heck reaction that links 4-vinylbenzaldehyde to a monoiodophthalocyanine

  使用其中液晶元将介晶性诱导为非介晶化合物的共混物，使得酞菁-[60]富勒烯（Pc-C 60）二元化合物自组织成液晶成为可能。PC-C 60个成对层1，2，或3，其中两个光活性单元由亚苯基亚乙烯基间隔件放在一起时，已通过Heck反应合成的链接4-乙烯基苯甲醛到monoiodophthalocyanine前体，然后通过甲亚胺叶立德的标准环加成产生从甲酰基Pc衍生物和N-甲基甘氨酸到C 60的双键之一。通过形成不同的混合物的介晶性质和热性质的液晶性酞菁4和成对层1，2，或3使用偏光显微镜（POM），差示扫描量热法（DSC），和X射线衍射（XRD）进行了研究。共混物的DSC图显示从晶态到中间相的清晰过渡，并且从粉末衍射实验获得的测量结构参数与盘状六方柱状（Col h）结构一致。考虑到在Pc-C 60 dyad和酞菁4的分离分子域中的偏析由于柱直径的不匹配和纯二元体缺乏介晶特性而将导致同构现象的发生