N-(2,6-diisopropylphen-yl)-9-bromo-perylene-3,4-dicarboximide | 165550-62-9

• 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-(2,6-diisopropylphen-yl)-9-bromo-perylene-3,4-dicarboximide
• 英文别名: 9-bromo-N-(2,6-diisopropylphenyl)perylene-3,4-dicarboximide；5-bromo-16-[2,6-di(propan-2-yl)phenyl]-16-azahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(20),2,4,6,8,10(23),11(21),12,14(22),18-decaene-15,17-dione
• CAS: 165550-62-9
• 化学式: C₃₄H₂₆BrNO₂
• 分子量: 560.49
• InChiKey: RSXVZKFFPWLZAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  718.0±60.0 °C(Predicted)
• 密度：
  1.438±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  38
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2,6-diisopropylphen-yl)-9-bromo-perylene-3,4-dicarboximide 在 四(三苯基膦)钯 四丁基氢氧化铵 、 碘 、 potassium carbonate 、 二甲基亚砜 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 25.0h， 生成 16-[2,6-Di(propan-2-yl)phenyl]-5-[3-(3-oxo-2,4,5-triphenylcyclopenta-1,4-dien-1-yl)phenyl]-16-azahexacyclo[12.6.2.12,6.011,21.018,22.010,23]tricosa-1(20),2,4,6,8,10(23),11(21),12,14(22),18-decaene-15,17-dione
  参考文献：
  名称：

  Fluorescence Detection from Single Dendrimers with Multiple Chromophores

  摘要：

  The differences in the fluorescence behavior of a polyphenylene dendrimer with eight peryleneimides chromophores (1) and a single hexaphenylperyleneimide chromophore have been investigated at a single-molecule level through the combination of ultrasensitive fluorescence detection and microscopy.

  DOI：

  10.1002/(sici)1521-3773(19991216)38:24<3752::aid-anie3752>3.0.co;2-y
• 作为产物：
  描述：

  2,6-二异丙基苯胺 在 咪唑 、 zinc diacetate 、 溴 作用下， 以 水 、 氯苯 为溶剂， 反应 28.5h， 生成 N-(2,6-diisopropylphen-yl)-9-bromo-perylene-3,4-dicarboximide
  参考文献：
  名称：

  r二酰亚胺-四苯乙二醛的合成及聚集诱导近红外发射。

  摘要：

  我们设计并合成了三联二亚胺-四苯乙二酮，它们具有特征性的聚集诱导的近红外荧光，最大发射波长可达800 nm。

  DOI：

  10.1039/c6cc01187j

文献信息

• Use of Rylene Derivatives as Photosensitizers in Solar Cells
  申请人：Pschirer Neil Gregory

  公开号：US20080269482A1

  公开（公告）日：2008-10-30

  Use of rylene derivatives I with the following definition of the variables: X together both —COOM; Y a radical -L-NR 1 R 2 (y1) -L-Z-R 3 (y2) the other radical hydrogen; together both hydrogen; R is optionally substituted (het)aryloxy, (het)arylthio; P is —NR 1 R 2 ; B is alkylene; optionally substituted phenylene; combinations thereof; A is —COOM; —SO 3 M; —PO 3 M 2 ; D is optionally substituted phenylene, naphthylene, pyridylene; M is hydrogen; alkali metal cation; [NR 5 ] 4 + ; L is a chemical bond; optionally indirectly bonded, optionally substituted (het)arylene radical; R 1 , R 2 are optionally substituted (cyclo)alkyl, (het)aryl; together optionally substituted ring comprising the nitrogen atom; Z is —O—; —S—; R 3 is optionally substituted alkyl, (het)aryl; R′ is hydrogen; optionally substituted (cyclo)alkyl, (het)aryl; R 5 is hydrogen; optionally substituted alkyl (het)aryl; m is 0, 1, 2; n, p m=0: 0, 2, 4 where: n+p=2, 4, if appropriate 0; m=1: 0, 2, 4 where: n+p=0, 2, 4; m=2: 0, 4, 6 where: n+p=0, 4, 6, or of mixtures thereof as photosensitizers in solar cells.

  使用以下变量定义的莱伦衍生物I的用途： X一起 两者都是-COOM; Y是一个基团 -L-NR 1 R 2 (y1) -L-Z-R 3 (y2) 另一个基团是氢; 一起 两者都是氢; R可选择地被取代为(het)芳氧基，(het)芳基硫基; P是-NR 1 R 2 ; B是烷基; 可选择地被取代的苯基; 它们的组合; A是-COOM; -SO 3 M; -PO 3 M 2 ; D可选择地被取代为苯基，萘基，吡啶基; M是氢; 碱金属阳离子; [NR 5 ] 4 + ; L是化学键; 可选择地间接键合，可选择地被取代的(het)芳基基团; R 1 ，R 2 可选择地被取代的(环)烷基，(het)芳基; 一起可选择地被取代的环，其中包括氮原子; Z是-O-; -S-; R 3 可选择地被取代的烷基，(het)芳基; R′是氢; 可选择地被取代的(环)烷基，(het)芳基; R 5 是氢; 可选择地被取代的烷基(het)芳基; m为0, 1, 2; n, p, m=0: 0, 2, 4其中：n+p=2, 4，如果适用为0; m=1: 0, 2, 4其中：n+p=0, 2, 4; m=2: 0, 4, 6其中：n+p=0, 4, 6， 或者作为太阳能电池中的光敏剂的混合物。
• Dye-functionalized head-to-tail coupled oligo(3-hexylthiophenes)—perylene–oligothiophene dyads for photovoltaic applications
  作者：Jens Cremer、Elena Mena-Osteritz、Neil G. Pschierer、Klaus Müllen、Peter Bäuerle

  DOI：10.1039/b414817g

  日期：——

  A series of novel donor–acceptor systems, consisting of head-to-tail coupled oligo(3-hexylthiophene)s covalently linked to perylenemonoimide, is described. These hybrid molecules, which differ by the length of the oligothiophene units from a monothiophene up to an octathiophene, were created via effective palladium-catalyzed Negishi and Suzuki cross-coupling reactions in good to excellent yields. The optical and electrochemical properties of these compounds were determined and based on this series structure–property relationships have been established which give vital information for the fabrication of photovoltaic devices. Because the synthesized perylenyl–oligothiophenes distinguish themselves by a high absorption between 300 and 550 nm and an almost complete fluorescence quenching of the perylene acceptor, they meet the requirements for organic solar cells.

  一系列新型供体-受体系统，由头对头耦合的3-己基噻吩寡聚物与芘单酰亚胺共价连接而成，被详细描述。这些混合分子因噻吩单元长度不同，从一噻吩至八噻吩，通过高效钯催化的Negishi和Suzuki交叉偶联反应在良好至极佳的产率下成功合成。这些化合物的光学和电化学特性已被测定，并基于这一系列结构-性质关系得以建立，为光伏器件的制造提供了关键信息。由于合成的芘基-噻吩寡聚物在300至550纳米之间具有高吸收能力，且芘受体的荧光几乎完全猝灭，它们满足了有机太阳能电池的要求。
• Synthesis and characterization of perylene–bithiophene–triphenylamine triads: studies on the effect of alkyl-substitution in p-type NiO based photocathodes
  作者：Martin Weidelener、Amaresh Mishra、Andrew Nattestad、Satvasheel Powar、Attila J. Mozer、Elena Mena-Osteritz、Yi-Bing Cheng、Udo Bach、Peter Bäuerle

  DOI：10.1039/c2jm16847b

  日期：——

  We report the synthesis of new donor–π–acceptor (D–π–A) dyes and their application in dye-sensitized solar cells (DSCs) with nickel(II) oxide (NiO)-based photocathodes. These D–π–A sensitizers incorporate a triphenylamine donor, a bithiophene π-bridge, and a perylenemonoimide (PMI) acceptor group. Two carboxylate groups attached to the triphenylamine afford strong anchoring to the NiO surface. The dyes in this series were varied firstly by the inclusion of an ethynyl linker between bithiophene and the triphenylamine moieties (1vs. 2), thereby increasing the length of the conjugated bridge. Despite very similar optoelectronic properties, the ethynyl-containing dye 2 showed a ∼25% improvement in power conversion efficiency in p-DSCs compared to 1, mostly attributed to the increased current density. Contrary to initial expectations, there was no major influence of the distance between the PMI unit of the dye and the NiO surface on the photoinduced dye anion lifetime, as measured by nanosecond transient absorption spectroscopy (TAS). Furthermore, altering the position of the alkyl chains on the bridging bithiophene in 3 and 4 resulted in a modest red shift in the dye absorption on account of increased charge delocalisation between the PMI and the π-bridge, owing to a reduced torsion angle between the PMI and the adjacent thiophene unit. Quantum-chemical DFT calculations were performed in order to evaluate these torsion angles and to study their influence on the electron density distribution in the relevant molecular orbitals. These changes of the molecular structure of the isomeric dyes 3 and 4 did not translate into improved photovoltaic performance, which is primarily attributed to lower charge photogeneration rates probed by transient absorption spectroscopy. While for p-type DSCs impressive overall solar-to-electric conversion efficiency of 0.04–0.10% under full sun illumination (simulated AM1.5G sunlight, 100 mW cm−2) and a broad incident photon to current efficiency (IPCE) response (350–700 nm) is demonstrated for these new dyes, the study clearly shows the need for judicious design rules for p-type sensitizers for application in photocathodic DSCs.

  我们报道了新型供体-π-受体（D-π-A）染料的合成及其在基于氧化镍（NiO）光阴极的染料敏化太阳能电池（DSC）中的应用。这些D-π-A敏化剂包含三苯胺供体、联噻吩π桥和苝酰亚胺（PMI）受体基团。两个连在三苯胺上的羧酸基团使染料与NiO表面牢固锚定。该系列染料首先通过在联噻吩和三苯胺单元之间引入乙炔连接基团（1 vs. 2）来变化，从而增加了共轭桥的长度。尽管光电性质非常相似，但含乙炔的染料2在p-DSC中与1相比显示了约25%的功率转换效率提升，这主要归因于电流密度的增加。与最初的预期相反，纳米秒瞬态吸收光谱（TAS）测量的结果显示，染料的PMI单元与NiO表面之间的距离对光诱导的染料阴离子寿命没有主要影响。此外，改变连接桥上的联噻吩上的烷基链的位置（3和4）导致染料吸收光谱的轻微红移，这是由于PMI和π桥之间的电荷离域增加，这是由于PMI和相邻噻吩单元之间的扭转角减小。进行了量子化学DFT计算，以评估这些扭转角并研究它们对相关分子轨道中电子密度分布的影响。异构体染料3和4的分子结构的这些变化并没有转化为光伏性能的改善，这主要是由于瞬态吸收光谱探测到的较低的电荷光生率。尽管对于p型DSC，在全太阳光照下（模拟AM1.5G阳光，100 mW cm⁻²）展示了令人印象深刻的总体光-电转换效率（0.04-0.10%）和广泛的入射光子-电流效率（IPCE）响应（350-700 nm），但对于这些新型染料的研究清楚地表明，在用于光阴极DSC的p型敏化剂的设计中，需要谨慎的设计规则。
• [EN] SYNTHESIS OF PERYLENE-PORPHYRIN BUILDING BLOCKS AND POLYMERS THEREOF FOR THE PRODUCTION OF LIGHT-HARVESTING ARRAYS<br/>[FR] SYNTHESE D'ELEMENTS CONSTITUTIFS A BASE DE PERYLENE-PORPHYRINE ET POLYMERES ASSOCIES DESTINES A LA PRODUCTION DE RESEAUX COLLECTEURS DE LUMIERE
  申请人：UNIV NORTH CAROLINA STATE

  公开号：WO2003105237A1

  公开（公告）日：2003-12-18

  The present invention provides methods, compounds, and compositions for the synthesis of light harvesting arrays, such arrays comprising: (a) a first substrate comprising a first electrode; and (b) a layer of light harvesting rods electrically coupled to said first electrode, each of said light harvesting rods comprising a polymer of Formula (I): wherein m is at least 1; X1 is a charge separation group, and X2 through Xm+1 are chromophores. At least one of X2 through Xm+1 has at least one perylene group coupled thereto.

  本发明提供了一种用于合成光收集阵列的方法、化合物和组合物，所述阵列包括：(a)包括第一电极的第一衬底；以及(b)与所述第一电极电性耦合的光收集棒层，其中每个所述光收集棒包括化学式(I)的聚合物：其中m至少为1；X1是一个电荷分离基团，X2至Xm+1是色素。X2至Xm+1中至少有一个与之耦合的苯菲啰基团。
• Synthesis of Perylene-3,4-mono(dicarboximide)−Fullerene C₆₀ Dyads as New Light-Harvesting Systems
  作者：Jérôme Baffreau、Lucie Ordronneau、Stéphanie Leroy-Lhez、Piétrick Hudhomme

  DOI：10.1021/jo800804z

  日期：2008.8.1

  Fullerene C60−perylene-3,4-mono(dicarboximide) (C60−PMI) dyads 1−3 were synthesized in the search for new light-harvesting systems. The synthetic strategy to the PMI intermediate used a cross-coupling Suzuki reaction for the introduction of a formyl group in the ortho, meta, or para position. Subsequent 1,3-dipolar cycloaddition with C60 led to the target C60−PMI dyad. Cyclic voltammetry showed that

  富勒烯C 60 -苝-3,4-单（二甲酰亚胺）（C 60 -PMI）二价基1 - 3中寻找新的捕光系统合成。PMI中间体的合成策略是使用交叉偶联的Suzuki反应在邻位，间位或对位引入甲酰基。随后的与C 60的1，3-偶极环加成导致目标C 60 -PMI dyad。循环伏安法表明，第一个单电子还原过程明确地发生在C 60部分上，随后的两个电子过程对应于随之发生的第二次C 60还原并首次降低了PMI。荧光的准定量淬火在成对显示出1 - 3，和建议的分子内能量转移从PMI发生富勒烯部分。这些C 60 -PMI双键构成了未来光伏应用的良好候选者，双方都有望获得明确定义的角色，即PMI充当光收集天线，而C 60在光敏层中扮演受体的角色。