9,10-dihydro-1,4-di(1-butoxy)-9,10[1',2']-benzenoanthracene-2,3-dicarbonitrile | 141989-75-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-dihydro-1,4-di(1-butoxy)-9,10[1',2']-benzenoanthracene-2,3-dicarbonitrile
• 英文别名: 3,6-Dibutoxypentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene-4,5-dicarbonitrile
• CAS: 141989-75-5
• 化学式: C₃₀H₂₈N₂O₂
• 分子量: 448.565
• InChiKey: CSZHDOXNOYARCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9,10-dihydro-1,4-di(1-butoxy)-9,10[1',2']-benzenoanthracene-2,3-dicarbonitrile 在 lithium 、 正丁醇 作用下， 反应 0.75h， 以47%的产率得到H2Pc(dib)4(OBu)8
  参考文献：
  名称：

  Method of minimizing absorption of visible light in ink compositions comprising infrared-absorbing macrocyclic cyanine dyes

  摘要：

  本发明提供了一种减少墨水组合物中可见光吸收的方法，所述墨水组合物包括一种红外吸收金属青菁染料，所述方法包括预先选择所述染料，使得所述金属至少有一个轴向配体与之结合，其中所述轴向配体包括适用于减少相邻染料分子之间的分子间相互作用的基团。该方法特别适用于与netpage和Hyperlabel系统相关联的使用。

  公开号：

  US07423145B2
• 作为产物：
  描述：

  2,3-dibromo-9,10-dihydro-9,10[1',2']-benzenoanthracene-1,4-dione 在 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 19.5h， 生成 9,10-dihydro-1,4-di(1-butoxy)-9,10[1',2']-benzenoanthracene-2,3-dicarbonitrile
  参考文献：
  名称：

  Synthesis, Photochemistry, and Electrochemistry of a Series of Phthalocyanines with Graded Steric Hindrance

  摘要：

  A group of twelve new and three known silicon phthalocyanines having axial ligands and peripheral groups which provide varying amounts of steric protection to the ring face and ring periphery has been assembled. These are SiPc[OSi(n-C6H13)(3)](2), 1, (known), SiPc[OSi(i-C4H9)(2)(n-C18H37)](2), 2, SiPc(OEt)(8)[OH](2), 5, SiPc(OEt)(8)[OSi(CH3)(3)](2), 6, SiPc(OnBu)(8)[OH](2), 8, (known), SiPc(OnBu)(8)[OSi(n-C6H13)(3)](2), 9, (known), SiPc(OnBu)(8)[OSi(i-C4H9)(2)(n-C18H37)](2), 10, SiPc(dib)(4)(OnBu)(8)[OH](2), 15, SiPc(dib)(4)(OnBu)(8)[F](2), 16, SiPc(dib)(4)(OnBu)(8)[OSi(n-C6H13)(2)](2), 17, SiPc(dib)(4)(OnBu)(8)[OSi(i-C4H9)(2)(n-C18H37)](2), 18, SiPc(dib)(4)(OnBu)(8)[OSi8O12(C5H9)(7)](2), 19, SiPc(dib)(4)(OnBu)(8)[OH](2), 22, SiPc(dib)(4)(OiBu)(8)[OSi(n-C6H13)(3)](2), 23, and SiPc(dib)(4)(OiBu)(8)[OSi8O12(C5H9)(7)](2), 24. Syntheses are given for the twelve members of the group that are new. Photophysical and voltammetric investigations of six representative members of the group, 1, 2, 10, 18, 19, and 24, have been carried out. The results show that compounds 1 and 2 (no butoxy substituents at the I and 4 positions) have significantly larger values of the first oxidation potential (E+1) than those compounds (10, 18, 19, and 24) that do carry these substituents. The values of E-1 (first reduction potential) show very little in the way of structural dependence. Alkoxy substitution at the 1,4 positions affects the HOMO energies, and therefore, the addition of an electron from an electrode to the LUMO of a 1,4 substituted silicon phthalocyanine will not be a sensitive function of the substitution pattern. The removal of an electron from the HOMO in an oxidation step on the other hand would be expected to be energetically less demanding for those compounds wherein the HOMO is higher lying. This orbital energy effect of substitution makes it clear why the E+1 values for compounds 1 and 2 are significantly lower. Substitution of dibenzobarreleno (dib) at the 2,3 positions has only minor effects on the HOMO energy, as shown by the similarities in the position of the Q-band maximum. However, it is very likely that the steric effects of the dibenzobarreleno substituents and the [OSi8O12(C5H9)(7)] axial cages contribute to the observed trends in E+1. Bimolecular rate constants for quenching of the triplet states of the six target compounds by O-2, by beta-carotene, and by chloranil were measured. The first two compounds quench by triplet-triplet (TT) energy transfer, whereas the last is an electron transfer (ET) reactant. All rate parameters were sensitive to the steric crowding of the phthalocyanine pi system, but with different degrees. The least sensitive was the ET reaction with chloranil.Thus, it appears that although steric crowding of the triplet state of the silicon phthalocyanines is very effective at reducing the rate constants of exoergic electron exchange energy transfer (TT) reactions, even for a small molecule such as oxygen, it is much less effective at discriminating against electron transfer (ET) processes. These differences may be accounted for on the concept that the overlap requirement for the double electron exchange of TT energy transfer is more stringent compared to the single electron transfer (ET).

  DOI：

  10.1021/jp027006q

文献信息

• Synthesis of metal cyanines
  申请人：Vonwiller Charlotte Simone

  公开号：US20060030702A1

  公开（公告）日：2006-02-09

  A method for preparing a macrocyclic metal cyanine, comprising the step of providing a macrocyclic metal-free cyanine precursor and inserting a metal therein using a metal reagent, wherein said metal reagent comprises at least one organic ligand.

  一种制备大环金属青霉素的方法，包括提供一种大环无金属青霉素前体，并使用金属试剂将金属插入其中的步骤，其中所述金属试剂包括至少一种有机配体。
• Cyanine dye having reduced visible absorption
  申请人：Vonwiller Charlotte Simone

  公开号：US20060030703A1

  公开（公告）日：2006-02-09

  The present invention provides an IR-absorbing macrocyclic cyanine dye, wherein said dye comprises at least one moiety for reducing intermolecular interactions, thereby minimizing absorption of visible light. Dyes of this type are especially suitable for use in netpage and Hyperlabel systems.

  本发明提供一种吸收红外光的大环氰染料，其中所述染料包括至少一种用于减少分子间相互作用的基团，从而最大程度地减少可见光的吸收。这种类型的染料特别适用于网页和超标签系统中的使用。
• [EN] METHOD OF MINIMIZING ABSORPTION OF VISIBLE LIGHT IN INFRARED DYES<br/>[FR] PROCEDE POUR MINIMISER L'ABSORPTION DE LA LUMIERE VISIBLE DANS LES COLORANTS INFRAROUGES
  申请人：SILVERBROOK RES PTY LTD

  公开号：WO2006015407A1

  公开（公告）日：2006-02-16

  The present invention provides a method of minimizing absorption of visible light in an IR-absorbing dye comprising reducing intermolecular interactions between adjacent dye molecules. The method is particularly suitable for use in connection with netpage and Hyperlabel systems.

  本发明提供了一种减少红外吸收染料中可见光吸收的方法，包括减少相邻染料分子之间的分子间相互作用。该方法特别适用于与netpage和Hyperlabel系统相关联的使用。
• US7278727B2
  申请人：——

  公开号：US7278727B2

  公开（公告）日：2007-10-09
• US7417141B2
  申请人：——

  公开号：US7417141B2

  公开（公告）日：2008-08-26