N,N'-bis(3-hydroxypropyl)-1,7-dibromoperylene-3,4:9,10-tetracarboxylic diimide | 1314078-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N,N'-bis(3-hydroxypropyl)-1,7-dibromoperylene-3,4:9,10-tetracarboxylic diimide
• 英文别名: 11,22-Dibromo-7,18-bis(3-hydroxypropyl)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2,4,9,11,13(23),14,16(24),20,25-decaene-6,8,17,19-tetrone
• CAS: 1314078-27-7
• 化学式: C₃₀H₂₀Br₂N₂O₆
• 分子量: 664.307
• InChiKey: HLSKRRDUTOGQSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(3-hydroxypropyl)-1,7-dibromoperylene-3,4:9,10-tetracarboxylic diimide 、 4,4'-双甲氧基三苯甲基氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis of a Dibromoperylene Phosphoramidite Building Block and Its Incorporation at the 5′ End of a G-Quadruplex Forming Oligonucleotide: Spectroscopic Properties and Structural Studies of the Resulting Dibromoperylene Conjugate

  摘要：

  Previous studies indicate that some perylene bisimide derivatives can drive the assembly of DNA G-quadruplexes, thus suggesting the possible advantage in the adoption of perylene-conjugated G-rich oligonucleotides in biological and biotechnological applications. Nevertheless, the typical poor solubility of perylene bisimides strongly limits the number of suitable chemical strategies to prepare perylene-conjugated oligonucleotides. In order to overcome these difficulties, we employed the earlier described core twisted perylene derivatives possessing unique optical and electronic properties, besides good solubility in common solvents. As a first result, the large-scale synthesis of a new dibromoperylene derivative (PEOEBr) phosphoramidite building block is herein reported. Furthermore, the structural behavior of the conjugated PEOEBr-GGGTTAGGG (HTRp2) human telomeric repeat was investigated by using CD, UV, fluorescence, and gel electrophoresis techniques in desalted water and in K+- and Na+-containing buffers. We observed that the peculiar property of PEOEBr moieties to form dimers instead of extended aggregates drives the HTRp2 strands toward dimerization and mainly promotes the formation of quadruplex species having both the 5'-ends located at the same side of the structures. However, the counterions present in solutions (K+ or Na+) as well as the strand concentration, also contribute to influence the topology and the stoichiometry of formed structures. Furthermore, unlike the unmodified sequence GGGTTAGGG (HTR2), HTRp2 strands quickly associate into G-quadruplexes even in desalted water, as assessed by CD experiments.

  DOI：

  10.1021/bc100526q
• 作为产物：
  描述：

  在 甲醇 、 氨 作用下， 以 水 为溶剂， 反应 2.0h， 生成 N,N'-bis(3-hydroxypropyl)-1,7-dibromoperylene-3,4:9,10-tetracarboxylic diimide
  参考文献：
  名称：

  Synthesis of a Dibromoperylene Phosphoramidite Building Block and Its Incorporation at the 5′ End of a G-Quadruplex Forming Oligonucleotide: Spectroscopic Properties and Structural Studies of the Resulting Dibromoperylene Conjugate

  摘要：

  Previous studies indicate that some perylene bisimide derivatives can drive the assembly of DNA G-quadruplexes, thus suggesting the possible advantage in the adoption of perylene-conjugated G-rich oligonucleotides in biological and biotechnological applications. Nevertheless, the typical poor solubility of perylene bisimides strongly limits the number of suitable chemical strategies to prepare perylene-conjugated oligonucleotides. In order to overcome these difficulties, we employed the earlier described core twisted perylene derivatives possessing unique optical and electronic properties, besides good solubility in common solvents. As a first result, the large-scale synthesis of a new dibromoperylene derivative (PEOEBr) phosphoramidite building block is herein reported. Furthermore, the structural behavior of the conjugated PEOEBr-GGGTTAGGG (HTRp2) human telomeric repeat was investigated by using CD, UV, fluorescence, and gel electrophoresis techniques in desalted water and in K+- and Na+-containing buffers. We observed that the peculiar property of PEOEBr moieties to form dimers instead of extended aggregates drives the HTRp2 strands toward dimerization and mainly promotes the formation of quadruplex species having both the 5'-ends located at the same side of the structures. However, the counterions present in solutions (K+ or Na+) as well as the strand concentration, also contribute to influence the topology and the stoichiometry of formed structures. Furthermore, unlike the unmodified sequence GGGTTAGGG (HTR2), HTRp2 strands quickly associate into G-quadruplexes even in desalted water, as assessed by CD experiments.

  DOI：

  10.1021/bc100526q

文献信息

• [EN] LIGHT HARVESTING ARRAY<br/>[FR] RÉSEAU COLLECTEUR DE LUMIÈRE
  申请人：FLUROSOL IND PTY LTD

  公开号：WO2015024064A1

  公开（公告）日：2015-02-26

  The invention relates to a light harvesting array or dye comprising an acceptor linked to a donor, wherein at least one of the acceptor or the donor is an oligomeric unit comprising a first optionally substituted rylene linked via a linker group to a second optionally substituted rylene, the first optionally substituted rylene is linked to the acceptor or the donor and the second optionally substituted rylene is capable of energy transfer to at least one of the first optionally substituted rylene, the acceptor or the donor. The invention also relates to compounds which may be used as light harvesting arrays, methods for their manufacture, and devices and materials comprising the light harvesting array or dye, for example, chromophoric materials, light guides, photobioreactors, photoluminescent algae systems, photodetectors, photovoltaic devices and luminescent/fluorescent solar concentrators.

  该发明涉及一种光收集阵列或染料，包括一个与给体相连的受体，其中受体或给体中至少有一个是包含第一可选择取代的芳香烃单元通过连接基团连接到第二可选择取代的芳香烃的寡聚单元，第一可选择取代的芳香烃与受体或给体相连，第二可选择取代的芳香烃能够将能量传递至第一可选择取代的芳香烃、受体或给体中的至少一个。该发明还涉及可用作光收集阵列的化合物，其制造方法，以及包括光收集阵列或染料的设备和材料，例如，色素材料、光导管、光生物反应器、光致发光藻类系统、光探测器、光伏器件和发光/荧光太阳能聚光器。
• LIGHT HARVESTING ARRAY
  申请人：FLUROSOL INDUSTRIES PTY LTD

  公开号：US20160211453A1

  公开（公告）日：2016-07-21

  The invention relates to a light harvesting array or dye comprising an acceptor linked to a donor, wherein at least one of the acceptor or the donor is an oligomeric unit comprising a first optionally substituted rylene linked via a linker group to a second optionally substituted rylene, the first optionally substituted rylene is linked to the acceptor or the donor and the second optionally substituted rylene is capable of energy transfer to at least one of the first optionally substituted rylene, the acceptor or the donor. The invention also relates to compounds which may be used as light harvesting arrays, methods for their manufacture, and devices and materials comprising the light harvesting array or dye, for example, chromophoric materials, light guides, photobioreactors, photoluminescent algae systems, photodetectors, photovoltaic devices and luminescent/fluorescent solar concentrators.

  该发明涉及一种光收集阵列或染料，包括一个与给体相连的受体，其中受体或给体中至少有一个是寡聚单元，包括第一可选取代瑞伦通过连接基团与第二可选取代瑞伦相连，第一可选取代瑞伦与受体或给体相连，第二可选取代瑞伦能够将能量传输至第一可选取代瑞伦、受体或给体中的至少一个。该发明还涉及可用作光收集阵列的化合物、其制造方法以及包括光收集阵列或染料的设备和材料，例如，色团材料、光导体、光生物反应器、荧光藻系统、光探测器、光伏器件和发光/荧光太阳能集中器。
• Light harvesting array
  申请人：FLUROSOL INDUSTRIES PTY LTD.

  公开号：US11322690B2

  公开（公告）日：2022-05-03

  The invention relates to a light harvesting array or dye comprising an acceptor linked to a donor, wherein at least one of the acceptor or the donor is an oligomeric unit comprising a first optionally substituted rylene linked via a linker group to a second optionally substituted rylene, the first optionally substituted rylene is linked to the acceptor or the donor and the second optionally substituted rylene is capable of energy transfer to at least one of the first optionally substituted rylene, the acceptor or the donor. The invention also relates to compounds which may be used as light harvesting arrays, methods for their manufacture, and devices and materials comprising the light harvesting array or dye, for example, chromophoric materials, light guides, photobioreactors, photoluminescent algae systems, photodetectors, photovoltaic devices and luminescent/fluorescent solar concentrators.

  本发明涉及一种光收集阵列或染料，包括与供体相连的受体，其中受体或供体中的至少一个是低聚物单元，该单元包括通过连接基团与第二任选取代的亚壬基烯相连的第一任选取代的亚壬基烯，第一任选取代的亚壬基烯与受体或供体相连，第二任选取代的亚壬基烯能够将能量转移到第一任选取代的亚壬基烯、受体或供体中的至少一个。本发明还涉及可用作采光阵列的化合物、其制造方法以及包含采光阵列或染料的装置和材料，例如，发色材料、导光板、光生物反应器、光发光藻类系统、光检测器、光伏装置和发光/荧光太阳能聚光器。