N-(2,6-diisopropylphenyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxymonoimide dibutyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: N-(2,6-diisopropylphenyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxymonoimide dibutyl ester
• 英文别名: Dibutyl 3,12-dibromo-16-[2,6-di(propan-2-yl)phenyl]-15,17-dioxo-16-azahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(21),2,4,6,8,10(23),11,13,18(22),19-decaene-5,7-dicarboxylate；dibutyl 3,12-dibromo-16-[2,6-di(propan-2-yl)phenyl]-15,17-dioxo-16-azahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(21),2,4,6,8,10(23),11,13,18(22),19-decaene-5,7-dicarboxylate
• 化学式: C₄₄H₄₁Br₂NO₆
• 分子量: 839.621
• InChiKey: BNNFIIPKCMCORW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  53
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2,6-diisopropylphenyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxymonoimide dibutyl ester 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以92%的产率得到N-(2,6-diisopropylphenyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxy monoimide monoanhydride
  参考文献：
  名称：

  Synthesis of Regioisomerically Pure 1,7-Dibromoperylene-3,4,9,10-tetracarboxylic Acid Derivatives

  摘要：

  The perylene derivative 1,7-dibromoperylene-3,4,9,10-tetracarboxylic tetrabutylester has been obtained in regioisomerically pure form, by employing a highly efficient, scalable, and robust synthesis starting from commercially available perylene-3,4,9,10-tetracarboxylic bisanhydride. Subsequently, this compound is utilized for the synthesis of extremely valuable and versatile regioisomerically pure intermediates, namely, 1,7-dibromoperylene-3,4,9,10-tetracarboxylic dibutylester monoanhydride, 1,7-dibromoperylene-3,4,9,10-tetracarboxylic bisanhydride, and 1,7-dibromoperylene monoimid monoanhydride. These compounds possess at least one anhydride functionality in addition to the 1,7 bromo substituents and thus allow for a virtually limitless attachment of substituents both at the "peri" and the "bay" positions. The intermediate 1,7-dibromoperylene monoimide monoanhydride is of special interest as it provides access to unsymmetrically imide-substituted 1,7-dibromoperylene derivatives, which are not accessible by previously known procedures. Finally, substitution of the 1,7 bromine atoms in the bay area by phenoxy groups, which is a generally applied reaction for 1,7-dibromoperylene bisimides, was proven to be equally effective for a 1,7-dibromoperylene tetraester and a 1,7-dibromoperylene diester monoimid.

  DOI：

  10.1021/jo501180a
• 作为产物：
  描述：

  1,7-dibromoperylene-3,4,9,10-tetracarboxy tetrabutyl ester 在 对甲苯磺酸 、 溶剂黄146 作用下， 以 N-甲基吡咯烷酮 、 正庚烷 为溶剂， 反应 53.0h， 生成 N-(2,6-diisopropylphenyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxymonoimide dibutyl ester
  参考文献：
  名称：

  Synthesis of Regioisomerically Pure 1,7-Dibromoperylene-3,4,9,10-tetracarboxylic Acid Derivatives

  摘要：

  The perylene derivative 1,7-dibromoperylene-3,4,9,10-tetracarboxylic tetrabutylester has been obtained in regioisomerically pure form, by employing a highly efficient, scalable, and robust synthesis starting from commercially available perylene-3,4,9,10-tetracarboxylic bisanhydride. Subsequently, this compound is utilized for the synthesis of extremely valuable and versatile regioisomerically pure intermediates, namely, 1,7-dibromoperylene-3,4,9,10-tetracarboxylic dibutylester monoanhydride, 1,7-dibromoperylene-3,4,9,10-tetracarboxylic bisanhydride, and 1,7-dibromoperylene monoimid monoanhydride. These compounds possess at least one anhydride functionality in addition to the 1,7 bromo substituents and thus allow for a virtually limitless attachment of substituents both at the "peri" and the "bay" positions. The intermediate 1,7-dibromoperylene monoimide monoanhydride is of special interest as it provides access to unsymmetrically imide-substituted 1,7-dibromoperylene derivatives, which are not accessible by previously known procedures. Finally, substitution of the 1,7 bromine atoms in the bay area by phenoxy groups, which is a generally applied reaction for 1,7-dibromoperylene bisimides, was proven to be equally effective for a 1,7-dibromoperylene tetraester and a 1,7-dibromoperylene diester monoimid.

  DOI：

  10.1021/jo501180a

文献信息

• Tunable and highly efficient light-harvesting antenna systems based on 1,7-perylene-3,4,9,10-tetracarboxylic acid derivatives
  作者：Rajeev K. Dubey、Damla Inan、Sanchita Sengupta、Ernst J. R. Sudhölter、Ferdinand C. Grozema、Wolter F. Jager

  DOI：10.1039/c6sc00386a

  日期：——

  attachment with perylene derivatives was based on the effective matching of their respective optical properties to achieve efficient excitation energy transfer (EET) by the Förster mechanism. A comprehensive study of the excited-state dynamics, in toluene, revealed quantitative and ultrafast (ca. 1 ps) intramolecular EET from donor naphthalene chromophores to the acceptor perylenes in all the studied

  我们报告了一系列五个双色光采光天线系统的合成和激发态动力学，这些系统能够有效地收集350-580 nm光谱范围内的太阳能。通过将吸收蓝光的萘单酰亚胺能量供体（D1，D2和D3）与吸收绿光的green 3,4,9,10-四羧酸衍生的能量受体共价连接，以模块化的方式合成了这些天线系统， 1,7-per-3,4,9,10-四羧酸四丁酯（A1），1,7-per-3,4,9,10-四羧酸单酰亚胺二丁酯（A2）和1,7-per-3 4,9,10-四羧酸双酰亚胺（A3）。能量供体已经连接在per衍生物的1,7-bay-位置上，因此使周围的位置自由用于进一步的功能化和装置构建。通过组成发色团之间的全芳香族非共轭苯氧基间隔基，已经实现了高度稳定和刚性的结构，在供体和受体组分之间没有电子连通。选择用于与derivatives衍生物连接的供体萘衍生物是基于它们各自的光学性质的有效匹配，以通过Förster机制实
• Substitution Effects on the Photoinduced Charge-Transfer Properties of Novel Perylene-3,4,9,10-tetracarboxylic Acid Derivatives
  作者：Damla Inan、Rajeev K. Dubey、Nick Westerveld、Jorrit Bleeker、Wolter F. Jager、Ferdinand C. Grozema

  DOI：10.1021/acs.jpca.7b03806

  日期：2017.6.22

  tuning the electron deficiency of perylene core. A comprehensive study of the photophysical properties of these molecules has shown a highly systematic trend in the magnitude of CT as a function of increased electron deficiency of the perylene core and solvent polarity. Importantly, just by changing the attachment of electron-donating group from “bay” to “imide” position, we are able to block the CT

  我们在这里报告了一系列电子供体-受体分子的合成和光物理研究，其中给电子体的4-甲氧基苯氧基与四个不同的per四羧酸衍生物（即per四酯1）的1,7-bay位置相连，per单酰亚胺二酯2，bi双酰亚胺3和per单苯并咪唑单酰亚胺4。使用这些per衍生物是因为它们从1移至4时电子接受能力的顺序增加。通过将供电子的4-甲氧基苯基连接到per单酰亚胺二酯2的酰亚胺位置上，可以合成另外两个供体-受体分子per二酰亚胺3。进行这项研究的动机是通过改变电子给体的位置并调节core核的电子缺陷来实现对per基体系中光诱导电荷转移（CT）过程的良好控制。对这些分子的光物理性质的全面研究表明，CT值的高系统性趋势是the原子核的电子缺乏和溶剂极性增加的函数。重要的是，仅通过将供电子基团的连接从“托架”位置更改为“酰亚胺”位置，我们就可以阻止CT过程。这意味着电子给体在per核上的定位强烈影响动力学的CT扫描过
• Synthesis of Perylene-3,4,9,10-tetracarboxylic Acid Derivatives Bearing Four Different Substituents at the Perylene Core
  作者：Rajeev K. Dubey、Nick Westerveld、Stephen J. Eustace、Ernst J. R. Sudhölter、Ferdinand C. Grozema、Wolter F. Jager

  DOI：10.1021/acs.orglett.6b02887

  日期：2016.11.4

  Nucleophilic aromatic substitution reactions on 1,7-dibromoperylene-3,4,9,10-tetracarboxylic monoimide dibutylester, using phenol and pyrrolidine reagents, have been exploited to synthesize perylenes with four different substituents at the perylene core. The first substitution is always regiospecific at the imide-activated 7-position. A second substitution reaction does not always replace the bromine

  已开发出使用苯酚和吡咯烷试剂在1,7-二溴per-3,4,9,10-四羧酸单酰亚胺二丁酯上进行亲核芳香取代反应，以合成在core中心具有四个不同取代基的per。第一次取代在酰亚胺激活的7位上始终是区域特异性的。第二取代反应并不总是取代C-1处的溴，而是可以取代高度活化的7位上的苯酚取代基。利用这种反应性模式，已经合成了“混合的” 1,7-二苯氧基，1,7-二吡咯烷基和两个1-苯氧基-7-吡咯烷基衍生物。
• Synthesis of Regioisomerically Pure 1,7-Dibromoperylene-3,4,9,10-tetracarboxylic Acid Derivatives
  作者：Sanchita Sengupta、Rajeev K. Dubey、Rob W. M. Hoek、Sjoerd P. P. van Eeden、D. Deniz Gunbaş、Ferdinand C. Grozema、Ernst J. R. Sudhölter、Wolter F. Jager

  DOI：10.1021/jo501180a

  日期：2014.7.18

  The perylene derivative 1,7-dibromoperylene-3,4,9,10-tetracarboxylic tetrabutylester has been obtained in regioisomerically pure form, by employing a highly efficient, scalable, and robust synthesis starting from commercially available perylene-3,4,9,10-tetracarboxylic bisanhydride. Subsequently, this compound is utilized for the synthesis of extremely valuable and versatile regioisomerically pure intermediates, namely, 1,7-dibromoperylene-3,4,9,10-tetracarboxylic dibutylester monoanhydride, 1,7-dibromoperylene-3,4,9,10-tetracarboxylic bisanhydride, and 1,7-dibromoperylene monoimid monoanhydride. These compounds possess at least one anhydride functionality in addition to the 1,7 bromo substituents and thus allow for a virtually limitless attachment of substituents both at the "peri" and the "bay" positions. The intermediate 1,7-dibromoperylene monoimide monoanhydride is of special interest as it provides access to unsymmetrically imide-substituted 1,7-dibromoperylene derivatives, which are not accessible by previously known procedures. Finally, substitution of the 1,7 bromine atoms in the bay area by phenoxy groups, which is a generally applied reaction for 1,7-dibromoperylene bisimides, was proven to be equally effective for a 1,7-dibromoperylene tetraester and a 1,7-dibromoperylene diester monoimid.