2,3,9,10,16,17,23,24-octakis(butyloxy)phthalocyaninato zinc(II) | 113654-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 2,3,9,10,16,17,23,24-octakis(butyloxy)phthalocyaninato zinc(II)
• 英文别名: ZINC;6,7,15,16,24,25,33,34-octabutoxy-2,11,20,29,37,39-hexaza-38,40-diazanidanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3,5,7,9,11,13,15,17,19(39),20,22,24,26,28,30(37),31,33,35-nonadecaene
• CAS: 113654-46-9
• 化学式: C₆₄H₈₀N₈O₈Zn
• 分子量: 1154.78
• InChiKey: RHQBRNPWNPLXLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.56
• 重原子数：
  81
• 可旋转键数：
  32
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,3,9,10,16,17,23,24-octakis(butyloxy)phthalocyaninato zinc(II) 、 碘 以 甲苯 为溶剂， 以69%的产率得到{Zn(2,3,9,10,16,17,23,24-octabutoxyphthalocyanine(2-))}*(I2)1.25
  参考文献：
  名称：

  Woehrle, Dieter; Schmidt, Volker, Journal of the Chemical Society, Dalton Transactions, 1988, p. 549 - 552

  摘要：

  DOI：
• 作为产物：
  描述：

  zinc diacetate 、 2,3,9,10,16,17,23,24-octabutoxyphthalocyanine 在 吡啶 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以71%的产率得到2,3,9,10,16,17,23,24-octakis(butyloxy)phthalocyaninato zinc(II)
  参考文献：
  名称：

  连接原子和取代基位置对酞菁中甲亚胺氮碱度的主要影响

  摘要：

  在一系列取代基位置不同的酞菁 (Pcs) 上研究了偶氮甲碱氮的碱度，[公式：见正文]外围（[公式：见正文]-系列）和非外围取代的 Pcs（[公式：见正文]-系列），以及一种取代基（烷基硫烷基、烷氧基或烷基）。通过亲核取代或 Negishi 偶联制备合适的 3,6-或 4,5-二取代邻苯二甲腈。目标锌Pcs采用Linstead法合成。碱度采用吸收法研究1用三氟乙酸滴定后，氯仿中的 H NMR 光谱。平衡常数（log [公式：见正文]）表明系列内有显着差异。碱度降低如下： [分子式：见正文]-烷氧基 ≫ [分子式：见正文]-烷硫基 > [分子式：见正文]-烷氧基 > [分子式：见正文]-烷基 > [分子式：见正文]-烷硫基 ∼ [公式：见正文]-log [公式：见正文]高于 7 至 2.6 M [公式：见正文]的烷基。[分子式：见正文]-烷氧基和 [分子式：见正文]-烷基硫烷基 Pcs 的碱度

  DOI：

  10.1142/s1088424616500747

文献信息

• Improvement of nonlinear optical properties of phthalocyanine bearing diethyleneglycole chains: Influence of symmetry lowering vs. heavy atom effect
  作者：Jonathan Britton、Alexander G. Martynov、David O. Oluwole、Yulia G. Gorbunova、Aslan Yu. Tsivadze、Tebello Nyokong

  DOI：10.1142/s1088424616501042

  日期：2016.8

  This paper reports the successful synthesis of the low symmetry phthalocyanines: metal-free 2,3-bis[2′-(2′′-hydroxyethoxy)ethoxy]-9,10,16,17,23,24-hexa-[Formula: see text]-butoxyphthalocyanine 1H[Formula: see text] and its zinc complex 1Zn along with their nonlinear optical (NLO) behavior in solution and in thin films. ¹H NMR investigations evidenced of higher dissymmetry of electronic density in 1H[Formula: see text] in comparison with 1Zn. This dissymmetry is responsible for unusually higher values of Im[[Formula: see text]]/[Formula: see text], [Formula: see text], and [Formula: see text] for 1H[Formula: see text]in contrast to 1Zn, where the notable effect of heavy-metal enhancement of ISC was expected. Both compounds showed Im[[Formula: see text]]/[Formula: see text] values of the order of 10[Formula: see text] in chloroform which are higher in comparison to the symmetrical octabutoxyphthalocyanine H₂[(BuO)₈Pc]. NLO properties of 1H[Formula: see text] were improved via its incorporation into polycarbonate polymeric matrix together with CdSe@CdS-TOPO quantum dots. In such composite the value of Im[[Formula: see text]]/[Formula: see text] was almost three times higher in comparison with 1H[Formula: see text] solution in chloroform. The obtained composites are expected to be perspective components of optical materials, capable of protection against strong light irradiation.

  本文报告了低对称性酞菁的成功合成：无金属 2,3-双[2′-(2′′-羟乙氧基)乙氧基]-9,10,16,17,23,24-六-[式：见正文]丁氧基酞菁 1H[式：见正文]及其锌配合物 1Zn，以及它们在溶液和薄膜中的非线性光学（NLO）行为。1H NMR 研究表明，与 1Zn 相比，1H[式：见正文] 的电子密度具有更高的不对称性。这种不对称性导致 1H[[式：见正文]]的 Im[[式：见正文]]/[式：见正文]、[式：见正文]和[式：见正文]值异常高，而 1Zn 的 Im[[式：见正文]]/[式：见正文]、[式：见正文]和[式：见正文]值异常高，在 1Zn 中，重金属对 ISC 的增强效果显著。这两种化合物在氯仿中的 Im[[式：见正文]]/[式：见正文]值都达到了 10[式：见正文]的数量级，与对称的八丁氧基酞菁 H2[(BuO)8Pc]相比更高。通过将 1H[式：见正文]与 CdSe@CdS-TOPO 量子点一起加入到聚碳酸酯聚合物基质中，1H[式：见正文]的 NLO 特性得到了改善。在这种复合材料中，Im[[式：见正文]]/[式：见正文]的值比 1H[[式：见正文]在氯仿中的溶液高出近三倍。所获得的复合材料有望成为光学材料的透视成分，能够抵御强光照射。
• Synthesis and spectral and electrochemical properties of 2,3,9,10,16,17,23,24-octabutylthiophthalocyaninatozinc(II)
  作者：Kazuhiro Takahashi、Makoto Kawashima、Yasuhiro Tomita、Makoto Itoh

  DOI：10.1016/0020-1693(94)04385-9

  日期：1995.4

  Abstract The title Zn(II) complex was synthesized, and its UV-Vis electronic absorption spectrum and cyclic voltammograms in N , N -dimethylformamide were measured. The Q and B bands appear around 704 and 370 nm, respectively. The two redox couples indicating reversible one-electron transfer processes appear in the reduction side of the cyclic voltammogram. Adsorption on an electrode surface and irreversible

  摘要合成了标题为Zn（II）的配合物，并测定了其在N，N-二甲基甲酰胺中的UV-Vis电子吸收光谱和循环伏安图。Q和B波段分别出现在704和370 nm附近。循环伏安图的还原侧出现两个表示可逆的单电子转移过程的氧化还原对。通过控制电位电解实验证实了在电极表面上的吸附和络合物分子分解引起的不可逆氧化。与2,3,9,10,16,17,23,24-八丁氧基酞菁酞菁相比，本配合物的Q和B谱带，还原电势和氧化电势分别向更长的波长，正方向和负方向移动（ II）。
• 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).