9-(chloromethyl)-10-hexylanthracene | 823788-51-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-(chloromethyl)-10-hexylanthracene
• 英文别名: 9-chloromethyl-10-hexylanthracene；9-(Chloromethyl)-10-hexylanthracene
• CAS: 823788-51-8
• 化学式: C₂₁H₂₃Cl
• 分子量: 310.867
• InChiKey: PLAYPCCPLZTIOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  methyl 4-((3,5-dihydroxyphenoxy)methyl)benzoate 、 9-(chloromethyl)-10-hexylanthracene 在 18-冠醚-6 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以87%的产率得到methyl 4-((3,5-bis((10-hexylanthracen-9-yl)methoxy)phenoxy)methyl)benzoate
  参考文献：
  名称：

  Mechanistic investigation of energy transfer in perylene-cored anthracene dendrimers

  摘要：

  在本出版物中，我们描述了针对聚焦于芘核蒽树枝状分子中定向能量转移详细机制的研究结果。为了获得确定的统计数据以探测能量转移途径，我们合成了四种类似的树枝状分子，旨在仅从远处的蒽基团向芘核分配能量。对这些树枝状分子的静态荧光研究表明，激发蒽基团会导致核发射，这表明能量转移效率很高。对所有十种树枝状分子获得的能量转移效率的检查表明，单步能量转移可能是这些树枝状分子中长距离能量传输的关键机制。

  DOI：

  10.1039/b716908f
• 作为产物：
  描述：

  聚合甲醛 、 9-己基蒽 在 盐酸 、 溶剂黄146 作用下， 反应 14.0h， 以89%的产率得到9-(chloromethyl)-10-hexylanthracene
  参考文献：
  名称：

  Synthesis and characterization of anthracene-clustering dendrimers: observation of fluorescence resonance energy transfer in the multichromophoric system

  摘要：

  A series of anthracene-clustering dendrimers bearing various aliphatic substituents at the terminal positions were synthesized using a direct coupling strategy. A remarkable effect of the side chains was imparted to chemical properties of the dendrimers such as drastically increased solubility. Although the multibranched anthracene arrays in the dendritic architectures exhibited no cooperativity in terms of the absorption feature and behaved as single chromophoric systems, investigations focusing on fluorescence properties revealed that a type of cooperativity was present as expressed in the reduced quantum yields of fluorescence. An alternative approach utilizing time-resolved fluorescence decay measurements clearly demonstrated that the most reasonable mechanism of the cooperative action should involve two discernible channels of intramolecular fluorescence resonance energy transfer (FRET) occurring from one chromophore to the others within and across junctions of the branching units. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.096

文献信息

• Evaluation of energy transfer in perylene-cored anthracene dendrimers
  作者：Masaki Takahashi、Hironao Morimoto、Kentaro Miyake、Mitsuji Yamashita、Hideki Kawai、Yoshihisa Sei、Kentaro Yamaguchi

  DOI：10.1039/b606215f

  日期：——

  Quantitative evaluation of Förster-type fluorescence resonance energy transfer (FRET) was undertaken by statistical investigations on perylene-cored anthracene dendrimers.

  对以苝为核心的蒽树枝状聚合物进行了荧光共振能量转移（FRET）的定量评估，采用了统计调查的方法。
• Construction of divergent anthracene arrays within dendritic frameworks
  作者：Masaki Takahashi、Hironao Morimoto、Yousuke Suzuki、Mitsuji Yamashita、Hideki Kawai、Yoshihisa Sei、Kentaro Yamaguchi

  DOI：10.1016/j.tet.2006.01.024

  日期：2006.3

  This publication presents simple methodologies for construction of divergent anthracene arrays either within structural interior or at peripheral positions of dendritic frameworks. The synthetic approaches employed multiple coupling reactions between two types of 10-functionalized 9-anthryl chlorides and two types of polyphenolic linkers, resulting in four types of dendritic architectures. Successful implementation of the syntheses was confirmed by a range of spectroscopies along with elemental analyses and size exclusion chromatography studies. The resulting dendritic molecules showed a range Of Solubilities in chloroform fairly affected by the dendritic backbone structures. Fluorescence spectroscopic experiments of the multichromophoric dendritic systems indicated pronounced energy delocalization functionalities via an energy migration within the branched molecular frameworks as expressed in reduced fluorescence quantum yields and complex emission decay profiles. (c) 2006 Elsevier Ltd. All rights reserved.
• Mechanistic investigation of energy transfer in perylene-cored anthracene dendrimers
  作者：Masaki Takahashi、Hironao Morimoto、Kentaro Miyake、Hideki Kawai、Yoshihisa Sei、Kentaro Yamaguchi、Tetsuya Sengoku、Hidemi Yoda

  DOI：10.1039/b716908f

  日期：——

  In this publication, we describe results of investigations focusing on detailed mechanisms of directed energy transfer in perylene-cored anthracene dendrimers. To obtain definitive statistical data for probing the energy transfer pathways, we synthesized four analogous dendrimers, which were designed to funnel the energy only from remote anthracene groups to the perylene cores. Static fluorescence studies with these dendrimers revealed that excitation of the anthracene groups led to the core emissions, indicating efficient energy transfer should be involved. Inspection of the energy transfer efficiencies obtained from all ten dendrimers demonstrated that single-step energy transfer should represent a key mechanism for the long-range energy transport in these dendrimers.

  在本出版物中，我们描述了针对聚焦于芘核蒽树枝状分子中定向能量转移详细机制的研究结果。为了获得确定的统计数据以探测能量转移途径，我们合成了四种类似的树枝状分子，旨在仅从远处的蒽基团向芘核分配能量。对这些树枝状分子的静态荧光研究表明，激发蒽基团会导致核发射，这表明能量转移效率很高。对所有十种树枝状分子获得的能量转移效率的检查表明，单步能量转移可能是这些树枝状分子中长距离能量传输的关键机制。
• Synthesis and characterization of anthracene-clustering dendrimers: observation of fluorescence resonance energy transfer in the multichromophoric system
  作者：Masaki Takahashi、Hironao Morimoto、Yousuke Suzuki、Tomoya Odagi、Mitsuji Yamashita、Hideki Kawai

  DOI：10.1016/j.tet.2004.09.096

  日期：2004.12

  A series of anthracene-clustering dendrimers bearing various aliphatic substituents at the terminal positions were synthesized using a direct coupling strategy. A remarkable effect of the side chains was imparted to chemical properties of the dendrimers such as drastically increased solubility. Although the multibranched anthracene arrays in the dendritic architectures exhibited no cooperativity in terms of the absorption feature and behaved as single chromophoric systems, investigations focusing on fluorescence properties revealed that a type of cooperativity was present as expressed in the reduced quantum yields of fluorescence. An alternative approach utilizing time-resolved fluorescence decay measurements clearly demonstrated that the most reasonable mechanism of the cooperative action should involve two discernible channels of intramolecular fluorescence resonance energy transfer (FRET) occurring from one chromophore to the others within and across junctions of the branching units. (C) 2004 Elsevier Ltd. All rights reserved.