[4,4-Dibutyl-5-(4-methyl-benzoyl)-8-p-tolyl-8H-3a,4a-diaza-4-stanna-s-indacen-3-yl]-p-tolyl-methanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [4,4-Dibutyl-5-(4-methyl-benzoyl)-8-p-tolyl-8H-3a,4a-diaza-4-stanna-s-indacen-3-yl]-p-tolyl-methanone
• 英文别名: [2,2-dibutyl-12-(4-methylbenzoyl)-8-(4-methylphenyl)-1,3-diaza-2-stannatricyclo[7.3.0.03,7]dodeca-4,6,9,11-tetraen-4-yl]-(4-methylphenyl)methanone
• 化学式: C₄₀H₄₄N₂O₂Sn
• 分子量: 703.512
• InChiKey: MRSDDMIVTJIVCT-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  9.61
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  44
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [4,4-Dibutyl-5-(4-methyl-benzoyl)-8-p-tolyl-8H-3a,4a-diaza-4-stanna-s-indacen-3-yl]-p-tolyl-methanone 、 5-(4-(5-(cyclooctatetraeneethynyl)-2,7-di-t-butyl-9,9-dimethylxanthene))dipyrromethane 在 sodium tetrahydroborate 、 ytterbium(III) triflate hydrate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 5-(2,7-di-t-butyl-9,9-dimethyl-4-(cyclooctatetraeneethynyl)xanthen-5-yl),10,15,20-tri(ptolyl)porphyrin
  参考文献：
  名称：

  迈向更光稳定，更明亮，光毒性更低的生色团：用环辛酸酯功能化的卟啉的合成和性质。

  摘要：

  已经获得了被称为辛酸三重态猝灭剂的分子辛酸环辛酯（COT）功能化的游离碱和卟啉锌，并通过结构，光谱和光物理技术对其进行了详细表征。用COT替代会导致卟啉三重态的固有寿命急剧下降。结果，无氧溶液中的光稳定性增加了两个到三个数量级。在非脱气溶液中，卟啉锌的光稳定性提高了约十倍，但游离碱的光稳定性降低了。在含有COT部分的游离碱和卟啉锌中光降解的相似量子产率表明了光化学分解的常见机理。预计新的卟啉的光毒性要小得多，因为单线态氧形成的量子产率由于三线态寿命较短而大大降低。三联体寿命的减少也应提高单分子态发射的卟啉发色团的亮度并减少闪烁，因为暗OFF状态的持续时间会更短。

  DOI：

  10.1002/chem.202001804
• 作为产物：
  描述：

  二丁基二氯化锡 、 对甲基苯甲酰氯 、 5-(4-methylphenyl)dipyrromethane 在 乙基溴化镁 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 、 二氯甲烷 为溶剂， 反应 0.5h， 以57%的产率得到[4,4-Dibutyl-5-(4-methyl-benzoyl)-8-p-tolyl-8H-3a,4a-diaza-4-stanna-s-indacen-3-yl]-p-tolyl-methanone
  参考文献：
  名称：

  Synthesis of porphyrins designed for attachment to electroactive surfaces via one or more carbon tethers

  摘要：

  描述了在5位点上具有表面附着基团的卟啉化合物。表面附着基团的化学式为：其中R为—CHCH2或—CCH，Ar为芳香基团。还描述了制备这类化合物所用的方法和中间体。

  公开号：

  US20060009638A1

文献信息

• 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.