4,5-bis(decylthio)phthalonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,5-bis(decylthio)phthalonitrile
• 英文别名: 4,5-Bis(decylsulfanyl)benzene-1,2-dicarbonitrile
• 化学式: C₂₈H₄₄N₂S₂
• 分子量: 472.803
• InChiKey: IMGBVSBCAKXJSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  32
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5-bis(decylthio)phthalonitrile 在 titanium(IV) isopropylate 、 尿素 作用下， 反应 24.0h， 以35%的产率得到2,3,9,10,16,17,23,24-octakis(decylthio)phthalocyaninatooxotitanium(IV)
  参考文献：
  名称：

  Solvent-Free Synthesis of Soluble, Near-IR Absorbing Titanyl Phthalocyanine Derivatives

  摘要：

  Solvent-free synthesis of a series of alkylthio-substituted titanyl phthalocyanine (TiOPc) derivatives starting from the corresponding phthalonitriles (Pn) is reported This methodology eliminates the formation of the unmetalated phthalocyanine (H2Pc), a side product that makes purification difficult The alkylthio groups on the reported derivatives enhance solubility in common organic solvents and shift the absorption to the near-IR region

  DOI：

  10.1021/jo1011637
• 作为产物：
  描述：

  1-癸硫醇 、 4,5-二氯邻苯二甲腈 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以56%的产率得到4,5-bis(decylthio)phthalonitrile
  参考文献：
  名称：

  新型锰酞菁配合物在溶液中的电化学、光谱和微观研究以及金上的自组装单分子层

  摘要：

  合成了四种新的锰 (III) 酞菁 (3a-d)，它们在外围位置分别被戊硫基、癸硫基、苄硫基和苯硫基八取代。表征了它们在溶液中以及作为金上自组装单分子层的特定电化学、光谱和微观特性。由于中心金属和给电子取代基的作用，紫外-可见光谱证实了所有配合物的 Q 波段红移。在四种配合物的循环伏安研究中可见三对氧化还原对，光谱电化学证实这些对对应于 Mn三个人电脑-2/锰二个人电脑-2(II) (金属还原), Mn二个人电脑-2/锰二个人电脑-3(III) (环减量) 和 Mn三个人电脑-1/锰三个人电脑-2（一）（环氧化）。电化学也被用来确定 MnPc 自组装单分子层在金上的阻塞特性，这被证明高度依赖于取代基的类型。其他表征方法包括 SAM 的拉曼光谱、原子力和扫描电化学显微镜分析。

  DOI：

  10.1142/s1088424610002471

文献信息

• Discotic liquid crystals of transition metal complexes 29: mesomorphism and charge transport properties of alkylthio-substituted phthalocyanine rare-earth metal sandwich complexes
  作者：Kazue Ban、Kaoru Nishizawa、Kazuchika Ohta、Anick M. van de Craats、John M. Warman、Iwao Yamamoto、Hirofusa Shirai

  DOI：10.1039/b003984p

  日期：——

  A series of bis[octakis(alkylthio)phthalocyaninato]rare-earth-metal(III) discotic compounds, [(CnS)8Pc]2M (M = Eu(III), Tb(III), Lu(III); n = 8, 10, 12, 14, 16, 18), has been synthesized. The mesomorphic and supramolecular structures have been investigated by using differential scanning calorimetry, polarization microscopy and temperature-dependent X-ray diffraction techniques. From the X-ray diffraction and spectroscopic results, it was revealed that in each of the rare-earth compound classes, [(CnS)8Pc]2Eu (n = 10, 12), [(CnS)8Pc]2Tb (n = 10, 12, 14) and [(CnS)8Pc]2Lu (n = 10, 12), derivatives were found which displayed a novel unique pseudo-hexagonal mesophase.The temperature dependence of the one-dimensional intracolumnar charge carrier mobilities, Σμ1D, has been measured for [(C12S)8Pc]2Lu and [(C18S)8Pc]2Lu using the PR-TRMC (pulse-radiolysis time-resolved microwave conductivity) technique. The mobility values in both the K and D phases are more than an order of magnitude larger than found previously for [(C12O)8Pc]2Lu and are close to the maximum values ever found for discotic materials. The lack of a decrease in Σμ1D at the mesophase to isotropic liquid transition suggests that these compounds may represent the first liquid phase organic semiconducting materials.

  一系列双[八烷基硫代邻苯二甲酰亚胺]稀土金属（III）盘状化合物[(CnS)8Pc]2M（M = Eu(III)、Tb(III)、Lu(III）；n = 8, 10, 12, 14, 16, 18）已被合成。通过差示扫描量热法、偏振显微镜和温度依赖的X射线衍射技术对各自的介晶态和超分子结构进行了研究。从X射线衍射和光谱结果显示，在每一类稀土化合物中，都发现了[(CnS)8Pc]2Eu（n = 10, 12）、[(CnS)8Pc]2Tb（n = 10, 12, 14）和[(CnS)8Pc]2Lu（n = 10, 12）衍生物，这些衍生物展现出了新颖的独特伪六角介相。通过脉冲辐解时分辨微波电导率（PR-TRMC）技术，测量了[(C12S)8Pc]2Lu和[(C18S)8Pc]2Lu的一维内列电荷载流子迁移率Σμ1D的温度依赖性。在K相和D相中的迁移率值均比以前在[(C12O)8Pc]2Lu中发现的高出一个数量级，并且接近于盘状材料所发现的最大值。在介相到各向同性液体过渡过程中Σμ1D没有降低，这表明这些化合物可能代表了首个液相有机半导体材料。
• Electrochemical, spectroscopic and microscopic studies of new manganese phthalocyanine complexes in solution and as self-assembled monolayers on gold
  作者：Megan Coates、Edith Antunes、Tebello Nyokong

  DOI：10.1142/s1088424610002471

  日期：2010.7

  octasubstituted at the peripheral position with pentylthio, decylthio, benzylthio, and phenylthio groups, respectively, were synthesized. Their specific electrochemical, spectroscopic and microscopic properties in solution and as self-assembled monolayers on gold were characterized. The UV-vis spectra confirmed red-shifted Q bands for all the complexes, due to the effect of the central metal and the electron-donating

  合成了四种新的锰 (III) 酞菁 (3a-d)，它们在外围位置分别被戊硫基、癸硫基、苄硫基和苯硫基八取代。表征了它们在溶液中以及作为金上自组装单分子层的特定电化学、光谱和微观特性。由于中心金属和给电子取代基的作用，紫外-可见光谱证实了所有配合物的 Q 波段红移。在四种配合物的循环伏安研究中可见三对氧化还原对，光谱电化学证实这些对对应于 Mn三个人电脑-2/锰二个人电脑-2(II) (金属还原), Mn二个人电脑-2/锰二个人电脑-3(III) (环减量) 和 Mn三个人电脑-1/锰三个人电脑-2（一）（环氧化）。电化学也被用来确定 MnPc 自组装单分子层在金上的阻塞特性，这被证明高度依赖于取代基的类型。其他表征方法包括 SAM 的拉曼光谱、原子力和扫描电化学显微镜分析。
• Discotic liquid crystals of transition metal complexes 27: supramolecular structure of liquid crystalline octakisalkylthiophthalocyanines and their copper complexes
  作者：Kazue Ban、Kaoru Nishizawa、Kazuchika Ohta、Hirofusa Shirai

  DOI：10.1039/b000134l

  日期：——

  A series of octakisalkylthiophthalocyanines, (CnS)8PcH2 (n = 8, 10, 12, 16), and their copper(II) complexes, (CnS)8PcCu (n = 8, 10, 12, 16), have been synthesized. Their mesomorphism and supramolecular structures have been investigated by using differential scanning calorimetry, polarizing microscopy, temperature-dependent X-ray diffraction technique and temperature-dependent electronic spectroscopy. From the X-ray diffraction and electronic spectral results, it was revealed that each of the compounds has a Dh mesophase in which columnar structures the molecules form a mixture of the parts of aggregated dimers and monomers. The shapes of dimers are discussed by exciton coupling theory (Kasha's rule).

  合成了一系列八烷基硫代酞菁（CnS）8PcH2（n = 8, 10, 12, 16）及其铜(II)复合物（CnS）8PcCu（n = 8, 10, 12, 16）。通过差示扫描量热法、偏光显微镜、温度依赖的X射线衍射技术以及温度依赖的电子光谱对其相行为和超分子结构进行了研究。从X射线衍射和电子光谱结果显示，每种化合物都具有Dh相，其中柱状结构的分子形成了聚集的二聚体和单体部分的混合物。通过激子耦合理论（Kasha规则）讨论了二聚体的形状。
• Novel columnar mesogen with octupolar optical nonlinearities: synthesis, mesogenic behavior and multiphoton-fluorescence-free hyperpolarizabilities of subphthalocyanines with long aliphatic chains†
  作者：Seok Ho Kang、Kimoon Kim、Yoon-Sok Kang、Wang-Cheol Zin、Geert Olbrechts、Kurt Wostyn、Koen Clays、Andre Persoons

  DOI：10.1039/a904254g

  日期：——

  Novel subphthalocyanines with long thioalkyl chains exhibit hexagonal columnar mesophases at room temperature; their inherent first hyperpolarizability values (β) measured by hyper-Rayleigh scattering (HRS) with fluorescence suppression are (189 ± 30) × 10–30 esu at 1300 nm.

  具有长硫烷基链的新型亚卟啉在室温下表现出六角柱状液晶相；其固有的第一超极化率值（β）通过超瑞利散射（HRS）在荧光抑制下测得为(189 ± 30) × 10⁻³⁰ esu，波长为1300 nm。
• ORGANIC PHOTOVOLTAIC DEVICES COMPRISING SOLUTION-PROCESSED SUBSTITUTED METAL-PHTHALOCYANINES AND EXHIBITING NEAR-IR PHOTO-SENSITIVITY
  申请人：McGrath Dominic V.

  公开号：US20130008503A1

  公开（公告）日：2013-01-10

  Organic photovoltaic (OPV) devices are disclosed. An exemplary device has first and second electrodes and an organic, photovoltaically active zone located between the first and second electrodes. The photovoltaically active zone includes an organic electron-donor material and an organic electron-acceptor material. The electron-donor material includes one or more trivalent- or tetravalent-metal phthalocyanines with alkylchalcogenide ring substituents, and is soluble in at least one organic solvent. This solubility facilitates liquid-processability of the donor material, including formation of thin-films, on an unlimited scale to form planar and bulk heterojunctions in organic OPVs. These donor materials are photovoltaically active in both visible and near-IR wavelengths of light, enabling more of the solar spectrum, for example, to be applied to producing electricity. Also disclosed are methods for producing the metalated phthalocyanines and actual devices.