4-(10-hydroxydecyloxy)phthalonitrile | 485331-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(10-hydroxydecyloxy)phthalonitrile
• 英文别名: 4-(10-Hydroxydecoxy)benzene-1,2-dicarbonitrile；4-(10-hydroxydecoxy)benzene-1,2-dicarbonitrile
• CAS: 485331-95-1
• 化学式: C₁₈H₂₄N₂O₂
• 分子量: 300.401
• InChiKey: XEXGESMLYVMQMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(10-hydroxydecyloxy)phthalonitrile 在 lithium 、 三乙胺 作用下， 以 二氯甲烷 、 戊醇 为溶剂， 反应 6.0h， 生成 2,9,16-tri(tert-butyl)-23-(10-methanesulfonyloxydecyloxy)phthalocyanine
  参考文献：
  名称：

  Synthesis and Self-Assembly of 2,9,16-Tri(tert-butyl)-23-(10-mercaptodecyloxy)phthalocyanine and the Application of Its Self-Assembled Monolayers in Organic Light-Emitting Diodes

  摘要：

  2,9,16-Tri(tert-butyl)-23-(10-mercaptodecyloxy)phthalocyanine (8) and its disulfide (9) have been synthesized and characterized, and their self-assembling behaviors on gold substrates have been studied. Characteristic Q-bands were observed at about 630 nm in the UV/visible spectra of the self-assembling monolayers (SAMs). They were broadened and blue-shifted relative to those observed in solution. Binding energies for S2p have the same values (161.70 eV) and are in accord with those for gold thiolates. The application of the SAMs in organic light-emitting diode was investigated. It shows that the SAM promotes the hole injection process from the anode.

  DOI：

  10.1002/1521-3765(20020916)8:18<4179::aid-chem4179>3.0.co;2-l
• 作为产物：
  描述：

  1,10-癸二醇 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 4-(10-hydroxydecyloxy)phthalonitrile
  参考文献：
  名称：

  Synthesis and Self-Assembly of 2,9,16-Tri(tert-butyl)-23-(10-mercaptodecyloxy)phthalocyanine and the Application of Its Self-Assembled Monolayers in Organic Light-Emitting Diodes

  摘要：

  2,9,16-Tri(tert-butyl)-23-(10-mercaptodecyloxy)phthalocyanine (8) and its disulfide (9) have been synthesized and characterized, and their self-assembling behaviors on gold substrates have been studied. Characteristic Q-bands were observed at about 630 nm in the UV/visible spectra of the self-assembling monolayers (SAMs). They were broadened and blue-shifted relative to those observed in solution. Binding energies for S2p have the same values (161.70 eV) and are in accord with those for gold thiolates. The application of the SAMs in organic light-emitting diode was investigated. It shows that the SAM promotes the hole injection process from the anode.

  DOI：

  10.1002/1521-3765(20020916)8:18<4179::aid-chem4179>3.0.co;2-l

文献信息

• Discotic liquid crystals of transition metal complexes 49: establishment of helical structure of fullerene moieties in columnar mesophase of phthalocyanine-fullerene dyads
  作者：Lisa Tauchi、Takahiro Nakagaki、Masahiro Shimizu、Eiji Itoh、Mikio Yasutake、Kazuchika Ohta

  DOI：10.1142/s1088424613500752

  日期：2013.11

  A homologous series of the phthalocyanine-fullerene dyads, C_n-PcM(OFbaC₆₀) (n = 6, 8, 10, 12; M = Cu , Ni , Co : 3a–3f) have been synthesized to obtain homeotropic alignment at rt and investigate the effects of spacer chain length (n = 6, 8, 10, 12) and central metal ( M = Cu , Ni , Co ) on the mesomorphism. Interestingly, the shorter-spacer-substituted (n = 6, 8; M = Cu ) dyads 3a and 3b showed a hexagonal columnar mesophase (Col_h), whereas the longer-spacer-substituted (n = 10, 12; M = Cu , Ni , Co ) dyads 3c–3f showed a tetragonal columnar mesophase (Col_tet). Moreover, each of the homologs 3a–3e shows perfect homeotropic alignment in both the Col_h and Col_tet mesophases at rt. More interestingly, these columnar mesophases gave a very unique XRD reflection peak denoted as Peak H in a very small angle region of 0.8 < 2θ < 2.0 degree. We have established at the first time from our developed two new XRD sample preparation techniques that the Peak H is due to the helical structure of fullerenes around columns formed by one-dimensionally stacked Pc cores. 1D nano array structure of donor and acceptor between two electrodes is recently proposed to obtain higher photoelectric conversion efficiency for organic thin film solar cells. This 1D nano array structure is almost compatible with the present homeotropically aligned Pc- C ₆₀ dyads 3a–3f between two glass plates. Hence, these novel Pc- C ₆₀ dyads 3a–3f may be very suitable to organic thin film solar cells.

  我们合成了一系列同源的酞菁-富勒烯二元体 Cn-PcM(OFbaC60)（n = 6、8、10、12；M = Cu、Ni、Co：3a-3f），以获得 rt 下的各向同性排列，并研究了间隔链长度（n = 6、8、10、12）和中心金属（M = Cu、Ni、Co）对介形的影响。有趣的是，较短间隔链取代（n = 6、8；M = Cu）的二元体 3a 和 3b 显示出六方柱状介相（Colh），而较长的间隔链取代（n = 10、12；M = Cu , Ni , Co）的二元体 3c-3f 显示出四方柱状介相（Coltet）。此外，每个同源物 3a-3e 在 rt 时都在 Colh 和 Coltet 介相中显示出完美的同向排列。更有趣的是，这些柱状介相在 0.8 < 2θ < 2.0 度的极小角度区域产生了一个非常独特的 XRD 反射峰，称为峰 H。通过我们开发的两种新的 XRD 样品制备技术，我们首次确定了 H 峰是由于富勒烯围绕由一维堆叠的 Pc 内核形成的柱的螺旋结构而产生的。最近，有人提出了在两个电极之间由供体和受体组成的一维纳米阵列结构，以获得更高的有机薄膜太阳能电池光电转换效率。这种 1D 纳米阵列结构与目前在两块玻璃板之间顺向排列的 Pc- C 60 二元体 3a-3f 几乎兼容。因此，这些新型 Pc- C 60 二元阵列 3a-3f 可能非常适用于有机薄膜太阳能电池。
• Synthesis of mesogenic phthalocyanine-C₆₀ donor–acceptor dyads designed for molecular heterojunction photovoltaic devices
  作者：Yves Henri Geerts、Olivier Debever、Claire Amato、Sergey Sergeyev

  DOI：10.3762/bjoc.5.49

  日期：——

  A series of phthalocyanine-C(60) dyads 2a-d was synthesized. Key steps in their synthesis are preparation of the low symmetry phthalocyanine intermediate by the statistical condensation of two phthalonitriles, and the final esterification of the fullerene derivative bearing a free COOH group. Structural characterization of the molecules in solution was performed by NMR spectroscopy, UV-vis spectroscopy

  合成了一系列酞菁-C(60) dyads 2a-d。它们合成的关键步骤是通过两种邻苯二甲腈的统计缩合制备低对称性酞菁中间体，以及带有游离 COOH 基团的富勒烯衍生物的最终酯化。溶液中分子的结构表征通过核磁共振光谱、紫外-可见光谱和循环伏安法进行。初步研究表明，一些制备的二元组形成了液晶 (LC) 中间相。据我们所知，这是 LC 酞菁-C(60) 二元组的第一个例子。
• Discotic liquid crystals of transition metal complexes 50: spiranthes-like supramolecular structure of phthalocyanine-fullerene dyads
  作者：Aya Ishikawa、Kenta Ono、Kazuchika Ohta、Mikio Yasutake、Musubu Ichikawa、Eiji Itoh

  DOI：10.1142/s1088424614500072

  日期：2014.5

  We have synthesized novel liquid crystalline Pc - C ₆₀ dyads (C_nS)₆PcCu-C₆₀ (n = 14, 16, 18: 1a–1c) by using our developed synthetic method in order to investigate the mesomorphism and alignment behavior. Each of the (C_nS)₆PcCu-C₆₀ dyads shows perfect homeotropic alignment in the Col_ho mesophase between two glass plates for n = 14, 16, 18 and also on a glass plate for n = 14, although none of the parent Pc compounds (C_nS)₈PcCu and the Pc precursors (C_nS)₆PcCu-OH and (C_nS)₆PcCu-OFBA shows homeotropic alignment. It may be attributed to the strong affinity between fullerene and glass surface. Although the reason is not so clear at the present time, this is very useful guideline for the molecular design to prepare homeotropic alignment-showing discotic liquid crystals. Very interestingly, the spherical C ₆₀ parts form a helical structure around the column formed by the disk-like Pc parts This supramolecular structure very resembles spiranthes. The spiranthes-like supramolecular structure is compatible with one-dimensional nano-array expecting the high conversion efficiency of solar cells.

  我们采用开发的合成方法合成了新型液晶 Pc - C 60 二元化合物 (CnS)6PcCu-C60 (n = 14, 16, 18: 1a-1c)，以研究其介形性和配位行为。n = 14、16、18 时，(CnS)6PcCu-C60 的每个二元体在两块玻璃板之间的 Colho 介相中都显示出完美的同向配位，n = 14 时在一块玻璃板上也显示出完美的同向配位，但母体 Pc 化合物 (CnS)8PcCu 和 Pc 前体 (CnS)6PcCu-OH 和 (CnS)6PcCu-OFBA 均未显示出同向配位。这可能是由于富勒烯与玻璃表面之间具有很强的亲和力。虽然目前还不清楚其中的原因，但这对分子设计制备各向同性配位的盘状液晶是非常有用的指导。非常有趣的是，球形的 C 60 部分在圆盘状的 Pc 部分形成的柱子周围形成螺旋结构，这种超分子结构非常像螺旋藻。这种类似螺旋藻的超分子结构与一维纳米阵列兼容，有望实现太阳能电池的高转换效率。
• Synthesis and Self-Assembly of 2,9,16-Tri(tert-butyl)-23-(10-mercaptodecyloxy)phthalocyanine and the Application of Its Self-Assembled Monolayers in Organic Light-Emitting Diodes
  作者：Xuebin Huang、Yunqi Liu、Shuai Wang、Shuqin Zhou、Daoben Zhu

  DOI：10.1002/1521-3765(20020916)8:18<4179::aid-chem4179>3.0.co;2-l

  日期：2002.9.16

  2,9,16-Tri(tert-butyl)-23-(10-mercaptodecyloxy)phthalocyanine (8) and its disulfide (9) have been synthesized and characterized, and their self-assembling behaviors on gold substrates have been studied. Characteristic Q-bands were observed at about 630 nm in the UV/visible spectra of the self-assembling monolayers (SAMs). They were broadened and blue-shifted relative to those observed in solution. Binding energies for S2p have the same values (161.70 eV) and are in accord with those for gold thiolates. The application of the SAMs in organic light-emitting diode was investigated. It shows that the SAM promotes the hole injection process from the anode.