2-[[4-(4-prop-2-enylhepta-1,6-dien-4-yl)phenyl]-(1H-pyrrol-2-yl)methyl]-1H-pyrrole | 878218-61-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-[[4-(4-prop-2-enylhepta-1,6-dien-4-yl)phenyl]-(1H-pyrrol-2-yl)methyl]-1H-pyrrole
• CAS: 878218-61-2
• 化学式: C₂₅H₂₈N₂
• 分子量: 356.511
• InChiKey: MQAMGGGLAJGJRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-[[4-(4-prop-2-enylhepta-1,6-dien-4-yl)phenyl]-(1H-pyrrol-2-yl)methyl]-1H-pyrrole 在 N-溴代丁二酰亚胺(NBS) 、 ytterbium(III) triflate 作用下， 以 吡啶 、 二氯甲烷 、 氯仿 为溶剂， 反应 1.0h， 生成 5-[4-(4-allylhepta-1,6-dien-4-yl)phenyl]-15-bromo-10,20-di-p-tolylporphyrin
  参考文献：
  名称：

  表面生成基于卟啉的多组分体系结构上逐步共价合成的研究

  摘要：

  卟啉已被证明是用于基于分子的信息存储应用中的可行介质。该应用的成功需要构建能够在制造过程中承受高温条件（高达400°C）的组件堆叠（“电活性表面/系链/电荷存储分子/连接剂/电解质/顶部接触”），以及操作（最高140°C）。为了确定能够在电活性表面上原位逐步合成共价连接结构的合适化学，已制备了三套锌卟啉（共22种）。在设计为在表面上形成基础层的套件中，每个卟啉均包含一个表面附着基团（三烯丙基三脚架或乙烯基单脚架）和一个远端官能团（例如五氟苯基，胺，溴，羧基），用于在表面附着后进行修饰。设计用于原位二联体构建的第二组结合了单个官能团（酒精，异硫氰酸根），该官能团与基本卟啉中的官能团互补。设计用于原位多联体构建的第三组以反式构型（卟啉中的5,15-位）结合了两个相同的官能团（溴，醇，活性亚甲基，胺，异硫氰酸根）。发现每个带有表面附着基团的卟啉都可以在Si（100）上形成优质的单层膜，如伏安和振

  DOI：

  10.1021/jo052650x
• 作为产物：
  描述：

  1-(4-allylhepta-1,6-dien-4-yl)-4-iodobenzene 在 indium(III) chloride 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 2-[[4-(4-prop-2-enylhepta-1,6-dien-4-yl)phenyl]-(1H-pyrrol-2-yl)methyl]-1H-pyrrole
  参考文献：
  名称：

  A Compact All-Carbon Tripodal Tether Affords High Coverage of Porphyrins on Silicon Surfaces

  摘要：

  Redox-active molecules designed to give high charge density on electroactive surfaces are essential for applications in molecular information storage. To achieve a small molecular footprint and thereby high surface charge density, a compound consisting of a triallyl tripod attached via a p-phenylene unit to a porphyrin (1) has been synthesized. The zinc chelate of 1 (Zn-1) was attached to Si(100). Electrochemical measurements indicate that the molecular footprint (75 A) in the monolayer is only similar to 50% larger than the minimum achievable, indicating high surface coverage. IR spectroscopy indicates that the bands due to the nu(C=C) (1638 cm(-1)) and gamma(CH) (915 cm-1) vibrations present in the solid sample (KBr pellet) are absent from the spectra of the monolayers of Zn-1, consistent with saturation of the double bond in each of the three legs of the tripod upon the hydrosilylation process accompanying attachment. Comparison of the relative intensities of the in-plane (998 cm-1) versus out-of-plane (797 cm-1) porphyrin modes indicates the average tilt angle (a) of the porphyrin ring with respect to the surface normal is similar to 46 degrees, a value also observed for analogous porphyrins tethered to Si(100) via monopodal carbon linkers. Accordingly, the higher packing densities afforded by the compact tripodal linker are not due to a more upright orientation on the surface. The charge-retention half-lives (t(1/2)) for the first oxidation state of the Zn-1 monolayers increase from 10 to 50 s at low surface coverage (1-5 x 10(-11) mol(.)cm(-2)) to near 200 s at saturation coverage (similar to 2 x 10(-10) mol(.)cm(-2)). Taken together, the high surface charge density (despite the lack of upright orientation) of the triallyl-tripodal porphyrin makes this construct a viable candidate for molecular information storage applications.

  DOI：

  10.1021/jo0510078

文献信息

• Multypodal tethers for high-density attachment of redox-active moieties to substrates
  申请人：Lindsey S. Jonathan

  公开号：US20070108438A1

  公开（公告）日：2007-05-17

  This invention provides redox-active molecules attached to polypodal (e.g., bipodal, tripodal, quadrapodal, pentapodal, etc.) tethers that can be used for attachment of the redox-active molecules to a substrate (e.g., an electrode). The tethered redox-active molecules are useful for the fabrication of memory devices.

  这项发明提供了与多脚（例如，双脚、三脚、四脚、五脚等）连接的氧化还原活性分子，可用于将这些氧化还原活性分子连接到基底（例如，电极）。连接的氧化还原活性分子可用于制作存储器件。
• Porphyrin Dyads Bearing Carbon Tethers for Studies of High-Density Molecular Charge Storage on Silicon Surfaces
  作者：Patchanita Thamyongkit、Lianhe Yu、Kisari Padmaja、Jieying Jiao、David F. Bocian、Jonathan S. Lindsey

  DOI：10.1021/jo0522761

  日期：2006.2.1

  [graphics]Redox-active molecules that afford high charge density upon attachment to an electroactive surface are of interest for use in molecular-based information- storage applications. One strategy for increasing charge density is to covalently link a second redox center to the first in an architecture that uses the vertical dimension in essentially the same molecular footprint. Toward this end, a set of four new porphyrin dyads have been prepared and characterized. Each dyad consists of two zinc porphyrins, an intervening linker (p-phenylene or 4,4'-diphenylethyne), and a surface attachment group (ethynyl or triallyl group). The porphyrin dyads were attached to an electroactive Si(100) surface and interrogated via electrochemical and FTIR techniques. The charge density obtainable for the ethynyl -functional ized porphyrin dyads is approximately double that observed for an analogously functionalized monomer, whereas that for the triallyl-functionalized dyads is at most 40% larger. These results indicate that the molecular footprint of the former dyads is similar to that of a monomer while that of the latter dyads is larger. For both the ethynyl- and triallyl-functionalized porphyrin dyads, higher charge densities (smaller molecular footprints) are obtained for the molecules containing the 4,4'-diphenylethyne versus the p-phenylene linker. This feature is attributed to the enhanced torsional flexibility of the former linker compared with that of the latter, which affords better packed monolayers. The FTIR studies indicate that the adsorption geometry of all the dyads is qualitatively similar and similar to that of monomers. However, the dyads containing the 4,4'-diphenylethyne linker sit somewhat more upright on the surface than those containing the p-phenylene linker, generally consistent with the smaller molecular footprint for the former dyads. Collectively, the high surface charge density (34-58 mu C center dot cm(-2)) of the porphyrin dyads makes these constructs viable candidates for molecular-information-storage applications.
• US8173630B2
  申请人：——

  公开号：US8173630B2

  公开（公告）日：2012-05-08
• [EN] MULTIPODAL TETHERS FOR HIGH-DENSITY ATTACHMENT OF REDOX-ACTIVE MOIETIES TO SUBSTRATES<br/>[FR] ATTACHES MULTIPODES PERMETTANT DES FIXATIONS A HAUTE DENSITE DE FRAGMENTS DE MOLECULES A ACTIVITE REDOX A DES SUBSTRATS
  申请人：UNIV CALIFORNIA

  公开号：WO2007053192A2

  公开（公告）日：2007-05-10

  [EN] This invention provides redox-active molecules attached to polypodal (e.g., bipodal, tripodal, quadrapodal, pentapodal, etc.) tethers that can be used for attachment of the redox-active molecules to a substrate (e.g., an electrode). The tethered redox-active molecules are useful for the fabrication of memory devices.
  [FR] L'invention porte sur des molécules à activité redox se fixant à des attaches polypodes (par exemple, bipodes, tripodes, quadrupodes, pentapodes, etc.) et pouvant servir à fixer lesdites molécules à un substrat (par exemple une électrode). Les molécules à activité redox attachées peuvent servir à la fabrication de dispositifs mémoires.
• A Compact All-Carbon Tripodal Tether Affords High Coverage of Porphyrins on Silicon Surfaces
  作者：Kisari Padmaja、Lingyun Wei、Jonathan S. Lindsey、David F. Bocian

  DOI：10.1021/jo0510078

  日期：2005.9.1

  Redox-active molecules designed to give high charge density on electroactive surfaces are essential for applications in molecular information storage. To achieve a small molecular footprint and thereby high surface charge density, a compound consisting of a triallyl tripod attached via a p-phenylene unit to a porphyrin (1) has been synthesized. The zinc chelate of 1 (Zn-1) was attached to Si(100). Electrochemical measurements indicate that the molecular footprint (75 A) in the monolayer is only similar to 50% larger than the minimum achievable, indicating high surface coverage. IR spectroscopy indicates that the bands due to the nu(C=C) (1638 cm(-1)) and gamma(CH) (915 cm-1) vibrations present in the solid sample (KBr pellet) are absent from the spectra of the monolayers of Zn-1, consistent with saturation of the double bond in each of the three legs of the tripod upon the hydrosilylation process accompanying attachment. Comparison of the relative intensities of the in-plane (998 cm-1) versus out-of-plane (797 cm-1) porphyrin modes indicates the average tilt angle (a) of the porphyrin ring with respect to the surface normal is similar to 46 degrees, a value also observed for analogous porphyrins tethered to Si(100) via monopodal carbon linkers. Accordingly, the higher packing densities afforded by the compact tripodal linker are not due to a more upright orientation on the surface. The charge-retention half-lives (t(1/2)) for the first oxidation state of the Zn-1 monolayers increase from 10 to 50 s at low surface coverage (1-5 x 10(-11) mol(.)cm(-2)) to near 200 s at saturation coverage (similar to 2 x 10(-10) mol(.)cm(-2)). Taken together, the high surface charge density (despite the lack of upright orientation) of the triallyl-tripodal porphyrin makes this construct a viable candidate for molecular information storage applications.