N-(4-Iodophenyl)-N'-(2,5-di-tert-butylphenyl)-3,4,9,10-perylenebis(dicarboximide) | 359857-37-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N-(4-Iodophenyl)-N'-(2,5-di-tert-butylphenyl)-3,4,9,10-perylenebis(dicarboximide)
• 英文别名: N-(2,5-di-tert-butylphenyl)-N'-(4-iodophenyl)-3,4,9,10-perylenetetracarboximide；N-(2,5-di-tert-butyl)-N'-(4-iodophenyl)-3,4,9,10-perylenetetracarboximide；7-(2,5-Ditert-butylphenyl)-18-(4-iodophenyl)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone
• CAS: 359857-37-7
• 化学式: C₄₄H₃₃IN₂O₄
• 分子量: 780.662
• InChiKey: SYHMMFYOVUIFHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  51
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10-[4-ethynylphenyl]-17,18-dihydro-18,18-dimethyl-5-(4-methylphenyl)-17-oxoporphinatozinc(II) 、 N-(4-Iodophenyl)-N'-(2,5-di-tert-butylphenyl)-3,4,9,10-perylenebis(dicarboximide) 在 tris(dibenzylideneacetone)dipalladium (0) tri-o-tolylphosphine 作用下， 以 三乙胺 、 甲苯 为溶剂， 以51%的产率得到N-(4-[2-[4-[17,18-dihydro-18,18-dimethyl-5-(4-methylphenyl)-17-oxoporphinatozinc(II)-10-yl]phenyl]ethnyl]phenyl)-N'(2,5-di-tert-butylphenyl)-3,4,9,10-perylene-bis(dicarboximide)
  参考文献：
  名称：

  Synthesis and Excited-State Photodynamics of Perylene-Bis(Imide)-Oxochlorin Dyads. A Charge-Separation Motif

  摘要：

  Three perylene-oxochlorin dyads have been prepared and characterized with the goal of identifying charge-injection or molecular-switching motifs for use in molecular photonics. Each dyad consists of a perylene-bis(imide) dye (PDI) joined at the 10-position of a magnesium, zinc, or free base (Fb) oxochlorin via a diphenylethyne linker. Each dyad has been studied in both polar and nonpolar media using static and time-resolved optical spectroscopy and electrochemical techniques. Dyad PDI-MgO is an excellent charge-separation unit in which the excited perylene (similar to3.5 ps lifetime) or the excited oxochlorin (lifetimes of 0.5 ns in benzonitrile and 1.0 ns in toluene) give rise to state PDI- MgO+ in high overall yield (>90%); the charge-separated state has a lifetime of greater than or equal to 1 ns in both toluene and benzonitrile. The pathway for generating PDI- MgPO+ from the excited perylene (PDI*) involves both hole transfer and energy transfer to the oxochlorin followed by electron transfer from the resulting MgO* to PDI. Similar decay of PDI* by energy transfer and hole transfer is found for dyads PDI-ZnO and PDI-FbO. However, electron-transfer quenching of the excited oxochlorin in these two dyads either does not occur or occurs to a much lesser degree than for PDI-MgO in both polar and nonpolar solvents. For PDI-FbO the decay of the charge-separated state occurs significantly by charge recombination to give the excited oxochlorin, making this a good light-harvesting system even though the early stages of the dynamics include charge separation/recombination. The observed differences in the extent of the possible excited-state processes (energy, hole, and electron transfer) among the dyads and in polar versus nonpolar media are consistent with the estimated energy ordering of the excited- and charge-separated states. This study has provided a new class of arrays containing perylene accessory pigments and oxochlorin chromophores that can be utilized for applications in light harvesting and molecular optoelectronics.

  DOI：

  10.1021/jp0269423
• 作为产物：
  描述：

  N,N'-双(2,5-二叔丁基苯基)-3,4,9,10-二甲酰亚胺 在 咪唑 、 氢氧化钾 、 zinc diacetate 作用下， 以 叔丁醇 为溶剂， 反应 3.0h， 生成 N-(4-Iodophenyl)-N'-(2,5-di-tert-butylphenyl)-3,4,9,10-perylenebis(dicarboximide)
  参考文献：
  名称：

  苝-卟啉二元化合物的合成和激发态光动力学。1. 通过二苯乙炔连接器进行平行能量和电荷转移

  摘要：

  已经检查了苝-卟啉二元组的光物理性质，目的是将该构造用于分子光子学应用。dyad 由通过二苯乙炔接头 (pep) 连接到锌卟啉 (Zn) 的苝双 (酰亚胺) 染料 (PDI) 组成。在极性和非极性溶剂中，光激发的苝单元 (PDI*) 通过能量转移到卟啉非常迅速地衰减（寿命为 2.5（甲苯）和 2.4 ps（乙腈）），以高产率形成 PDI-pep-Zn*（ 80%，甲苯；70% 乙腈），空穴转移到卟啉，形成 PDI--pep-Zn+，产率较低（20%，甲苯；30% 乙腈）。在甲苯和乙腈中，Zn* 激发态随后主要通过电子转移到苝（形成 PDI--pep-Zn+）以 0.4 ns 的寿命衰减（80%）。在非极性溶剂（甲苯）中，

  DOI：

  10.1021/jp010335i