9,22-dibutoxyhemiporphyrazin | 148964-76-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 9,22-dibutoxyhemiporphyrazin
• 英文别名: 9,22-bis(dibutoxy)hemiporphyrazine；9,22-bis(di-n-butoxy)hemiporphyrazine；5,20-Dibutoxy-2,8,17,23,31,32,33,34-octazaheptacyclo[22.6.1.13,7.19,16.118,22.010,15.025,30]tetratriaconta-1,3,5,7,9(33),10,12,14,16,18,20,22,24(31),25,27,29-hexadecaene；5,20-dibutoxy-2,8,17,23,31,32,33,34-octazaheptacyclo[22.6.1.13,7.19,16.118,22.010,15.025,30]tetratriaconta-1,3,5,7,9(33),10,12,14,16,18,20,22,24(31),25,27,29-hexadecaene
• CAS: 148964-76-5
• 化学式: C₃₄H₃₂N₈O₂
• 分子量: 584.68
• InChiKey: NDEZSBWIKCDYTC-UHFFFAOYSA-N

物化性质

• 沸点：
  859.2±60.0 °C(predicted)
• 密度：
  1.309±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  44
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9,22-dibutoxyhemiporphyrazin 在 lead acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以80%的产率得到9,22-bis-(dibutoxy)hemiporphyrazinato lead
  参考文献：
  名称：

  Large Two-Photon Absorption Cross Sections of Hemiporphyrazines in the Excited State: The Multiphoton Absorption Process of Hemiporphyrazines with Different Central Metals

  摘要：

  A series of five hemiporphyrazines (Hps) with different coordinating central atoms (H-2, GeCl2, InCl, Pt, Pb), and the acyclic derivative 1,3-bis-(6'-amino-4'-butoxy-2'-pyridylimino)-1,3-dihydroisoindoline have been synthesized and their multiphoton absorption properties examined at the second harmonic frequency of the Nd:YAG laser in the nanosecond time regime. Metal-free and platinum Hps display saturation of optical transmittance within incident fluence values of 6 J cm(-2). Comparison with other similar molecular structures like phthalocyanines and related molecules shows that Hps are strong nonlinear absorbers. The experimental curves of nonlinear transmission at 532 nm have been fitted by means of a three-level model with the occurrence of simultaneous two-photon absorption from an excited state. In the sole case of the lnCI complex we found that a five-level model is needed because of the participation of triplet states. Contrary to phthalocyanines, naphthalocyanines, and porphyrins, a heavy central atom does not improve the nonlinear absorption properties since a different excited states dynamic is involved. The large nonlinear absorption of Hps combined with the very small absorption in the visible spectral range makes these molecules a very interesting class of molecules for nonlinear optical applications.

  DOI：

  10.1021/ja802678u
• 作为产物：
  描述：

  1,3-二亚胺基异吲哚啉 、 4-丁氧基吡啶-2,6-二胺 以 正丁醇 为溶剂， 以26%的产率得到9,22-dibutoxyhemiporphyrazin
  参考文献：
  名称：

  Demonstration of the optical limiting effect for an hemiporphyrazine

  摘要：

  半多齿吡咯类化合物9,22-二（正丁氧基）半多齿吡咯盐酸铟(III)（1）是该类化合物中为数不多的例子之一，它在可见光谱内对纳秒激光脉冲显示出反向饱和吸收的非线性光学效应。其高线性透射率与在相同光谱范围内（400–650 nm）快速切换至强吸收激发态的特性，使得该半多齿吡咯类化合物成为脉冲辐射被动快门的理想材料。

  DOI：

  10.1039/b601591c

文献信息

• Crystal Structure of μ-Oxo-bis[9,22-(bisbutyloxy)hemiporphyrazinato]iron(III)
  作者：Klaus Haberroth、Michael Hanack、Cäcilia Maichle-Mössmer

  DOI：10.1002/zaac.200500422

  日期：2006.2

  The crystal structure of the title compound, C68H60N16O5Fe2, shows a dinuclear complex of two crystallographically independent, distorted hemiporphrazinato iron complexes with five-coordinate iron and oxygen as bridging ligand. The Fe1-O1-Fe2 angle is 151.16°, the Fe-O bond lengths are Fe1-O1 [1.771(2) A] and Fe2-O1 [1.773(2) A]. The dinuclear complexes have a staggered conformation with a dihedral

  标题化合物 C68H60N16O5Fe2 的晶体结构显示了两种晶体学独立、扭曲的半卟啉铁配合物的双核配合物，其中五配位铁和氧作为桥接配体。Fe1-O1-Fe2角为151.16°，Fe-O键长为Fe1-O1[1.771(2)A]和Fe2-O1[1.773(2)A]。双核复合物具有交错构象，二面角为 26.2°，但未观察到同轴形成四聚体单元。该分子的特点是短的Fe-N（异吲哚）键[1.998（3）A]和长的Fe-N（吡啶）键，数值范围从[2.175(3)A]到[2.245(3)A] .
• Hanack, Michael; Haberroth, Klaus; Rack, Michael, Chemische Berichte, 1993, vol. 126, # 5, p. 1201 - 1204
  作者：Hanack, Michael、Haberroth, Klaus、Rack, Michael

  DOI：——

  日期：——
• Large Two-Photon Absorption Cross Sections of Hemiporphyrazines in the Excited State: The Multiphoton Absorption Process of Hemiporphyrazines with Different Central Metals
  作者：Danilo Dini、Mario J.F. Calvete、Michael Hanack、Vincenzo Amendola、Moreno Meneghetti

  DOI：10.1021/ja802678u

  日期：2008.9.17

  A series of five hemiporphyrazines (Hps) with different coordinating central atoms (H-2, GeCl2, InCl, Pt, Pb), and the acyclic derivative 1,3-bis-(6'-amino-4'-butoxy-2'-pyridylimino)-1,3-dihydroisoindoline have been synthesized and their multiphoton absorption properties examined at the second harmonic frequency of the Nd:YAG laser in the nanosecond time regime. Metal-free and platinum Hps display saturation of optical transmittance within incident fluence values of 6 J cm(-2). Comparison with other similar molecular structures like phthalocyanines and related molecules shows that Hps are strong nonlinear absorbers. The experimental curves of nonlinear transmission at 532 nm have been fitted by means of a three-level model with the occurrence of simultaneous two-photon absorption from an excited state. In the sole case of the lnCI complex we found that a five-level model is needed because of the participation of triplet states. Contrary to phthalocyanines, naphthalocyanines, and porphyrins, a heavy central atom does not improve the nonlinear absorption properties since a different excited states dynamic is involved. The large nonlinear absorption of Hps combined with the very small absorption in the visible spectral range makes these molecules a very interesting class of molecules for nonlinear optical applications.
• Demonstration of the optical limiting effect for an hemiporphyrazine
  作者：Danilo Dini、Mario J. F. Calvete、Michael Hanack、Vincenzo Amendola、Moreno Meneghetti

  DOI：10.1039/b601591c

  日期：——

  The hemiporphyrazine complex 9,22-bis(dibutoxy)hemiporphyrazinato chloroindium(III) (1) is one of the few examples for this class of compounds, which displays the nonlinear optical effect of reverse saturable absorption for nanosecond laser pulses in the visible spectrum. The high linear transmission combined with the fast switching into a strongly absorbing excited state in the same spectral range (400–650 nm), renders the studied hemiporphyrazine an ideal material for the passive shuttering of pulsed radiations.

  半多齿吡咯类化合物9,22-二（正丁氧基）半多齿吡咯盐酸铟(III)（1）是该类化合物中为数不多的例子之一，它在可见光谱内对纳秒激光脉冲显示出反向饱和吸收的非线性光学效应。其高线性透射率与在相同光谱范围内（400–650 nm）快速切换至强吸收激发态的特性，使得该半多齿吡咯类化合物成为脉冲辐射被动快门的理想材料。