3-溴芘 | 23683-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 3-溴芘
• 中文别名: 3-溴苝
• 英文名称: 3-bromoperylene
• 英文别名: 3-Brom-perylen
• CAS: 23683-68-3
• 化学式: C₂₀H₁₁Br
• 分子量: 331.211
• InChiKey: GPBMCEWKAPSTOU-UHFFFAOYSA-N

物化性质

• 熔点：
  245-246 °C
• 沸点：
  512.0±19.0 °C(Predicted)
• 密度：
  1.560±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2903399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温下应存放在干燥且密封的容器中。

反应信息

• 作为反应物：
  描述：

  3-溴芘 在 吡啶 、 甲醇 、 正丁基锂 、 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 5'-(4,4'-dimethoxytrityl)-3-perylene-1'-α-D-2'-deoxyriboside
  参考文献：
  名称：

  Modified DNA Analogues That Sense Light Exposure with Color Changes

  摘要：

  We report the discovery of a new class of light-sensing molecules. These light sensors are composed of fluorophore oligomers assembled on a DNA backbone. A combinatorial library of tetrafluorophores consisting of over 14 000 compounds was synthesized and screened for rapid responses toward light exposure. Among the most light-sensitive molecules, at least three tetramers were found to respond to light exposure with apparent color changes, rather than simple photobleaching.

  DOI：

  10.1021/ja046910o
• 作为产物：
  描述：

  苝 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 生成 3-溴芘
  参考文献：
  名称：

  自旋允许的跃迁控制正交供体-受体二元组中三重态激发态的形成。

  摘要：

  三重态激发态（三重态）是从有机合成到生物医学再到分子电子学等关键技术和过程的关键中间体。没有重原子的三重π共轭有机分子的生产仍然具有挑战性。自旋轨道，电荷转移系统间交叉（SOCT-ISC）将单重态电荷分离态直接转换为电子供体-受体（DA）对中的三重态。在这里，使用一系列正交的DA型硼二吡咯亚甲基（BODIPY）衍生物作为模型系统，我们表明三联体的形成很大程度上受自旋允许的跃迁控制，而不是受SOCT-ISC的控制。然而，在（π，π*）状态之间，SOCT-ISC过程仍比普通ISC进行得快得多，这是因为SOCT-ISC的自旋轨道耦合强了2个数量级。我们进一步表明，这样的过程可以在非三重峰形成分子per中产生三重峰。我们的发现揭示了禁止自旋过程的明确物理基础，并为利用该过程的未来分子设计提供了指导。

  DOI：

  10.1016/j.chempr.2018.10.001

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。
• Efficient synthesis of fluorescent alkynyl C-nucleosides via Sonogashira coupling for the preparation of DNA-based polyfluorophores
  作者：Dominik K. Kölmel、Luzi J. Barandun、Eric T. Kool

  DOI：10.1039/c6ob01199c

  日期：——

  A facile and general procedure for the preparation of alkynyl C-nucleosides with varied fluorophores is presented. Sonogashira coupling was used as a key reaction to conjugate the dyes to an easily accessible ethynyl functionalized deoxyribose derivative. The new C-nucleosides were used for the preparation of DNA-based polyfluorophores.

  提出了一种制备具有各种荧光团的炔基C-核苷的简便而通用的方法。Sonogashira偶联被用作关键反应，以使染料与易于获得的乙炔基官能化的脱氧核糖衍生物缀合。新的C-核苷用于制备基于DNA的多荧光团。
• Design and synthesis of multi-component 18π annulenic fluorofullerene ensembles suitable for donor–acceptor applications
  作者：Glenn A. Burley、Anthony G. Avent、Ilya V. Gol’dt、Peter B. Hitchcock、Hamad Al-Matar、Demis Paolucci、Francesco Paolucci、Patrick W. Fowler、Alessandro Soncini、Joan M. Street、Roger Taylor

  DOI：10.1039/b309959h

  日期：——

  A series of trannulene (all-trans annulene) derivatives of [60]fullerene have been prepared by reacting C60F18 with methanetricarboxylate esters that incorporate a range of photoactive functions. All the compounds have the intense emerald-green colour of fullerene trannulenes, characterised by strong bands at ca. 612 and 667 nm. Single crystal X-ray studies show that the packing varies with the nature of the addend, attributable to differing steric effects. UV/vis absorption spectra display transitions of the respective fullerene and addend models, indicating absence of electronic interactions between them in the ground state. These now provide an extensive series for testing photoactive (light-harvesting) properties, with the exceptional properties of having strong visible light absorption. Their exceptional stability is attributed to the 18π aromatic circuit, inability to undergo nucleophilic substitution without disrupting this circuit, and a curved cage region that is shielded to reagents by the three bulky addends.

  一系列由[60]富勒烯构成的全反式环烯（trannulene）衍生物已通过C60F18与含有多种光活性功能团的甲烷三羧酸酯反应制备而成。所有化合物都呈现出富勒烯环烯特有的深祖母绿色，其特征在于约612和667纳米处的强吸收带。单晶X射线研究表明，由于空间效应的差异，包合物随附加基团性质的不同而变化。UV/可见光吸收光谱显示了各自富勒烯模型和附加基团的跃迁，表明在基态时它们之间不存在电子相互作用。这些化合物如今提供了一大批用于测试光活性（光捕获）性能的系列，其独特之处在于具有强烈的可见光吸收。它们异常的稳定性归因于18π芳香环路，无法在不破坏此环路的情况下进行亲核取代反应，以及由三个庞大的附加基团保护的弯曲笼状区域。
• PHOSPHINE COMPOUND, PROCESS FOR PRODUCING THE SAME, AND PEROXIDE SCAVENGER USING THE SAME
  申请人：Shioji Kosei

  公开号：US20110015440A1

  公开（公告）日：2011-01-20

  The invention provides a novel peroxide scavenger comprising a phosphine compound represented by general formula [I]: wherein Z 1 and Z 2 each represents a cyclic group; Ar represents an arylene group; R represents an aliphatic hydrocarbon group; Y represents phosphorus (P), nitrogen (N), or bismuth (Bi); and R 1 , R 2 , and R 3 each represents a cyclic group, particularly a peroxide scavenger that can scavenge peroxides such as reactive oxygen species which are generated in mitochondria upon exposure to oxidative stress and localized in mitochondria. The phosphine compound of the invention is oxidized by the peroxides localized in mitochondria to increase the fluorescence intensity, whereby the peroxides can be scavenged.

  该发明提供了一种新型过氧化物清除剂，包括由通式[I]所表示的膦化合物：其中Z1和Z2分别表示环状基团；Ar表示芳基基团；R表示脂肪烃基团；Y表示磷（P）、氮（N）或铋（Bi）；而R1、R2和R3分别表示环状基团，特别是一种过氧化物清除剂，可以清除在暴露于氧化应激时在线粒体中生成并定位在线粒体中的反应性氧化物种，该发明的膦化合物被定位在线粒体中的过氧化物氧化以增加荧光强度，从而可以清除过氧化物。
• Synthesis of Spiropyrans As Building Blocks for Molecular Switches and Dyads
  作者：Christoph Beyer、Hans-Achim Wagenknecht

  DOI：10.1021/jo100309r

  日期：2010.4.16

  The synthesis of spiropyrans was improved significantly with use of ultrasonic radiation. To show the broad applicability of this methodology a range of spiropyrans were prepared which are equipped with iodo, hydroxyl, ethinyl, or azido groups as potential building blocks for conjugation to functional π-systems or biopolymers. Representatively, the conjugation chemistry was demonstrated for the preparation

  螺吡喃的合成通过使用超声辐射而得到显着改善。为了显示该方法的广泛适用性，制备了一系列螺并吡喃并带有碘，羟基，乙炔基或叠氮基，作为与功能性π-系统或生物聚合物结合的潜在结构单元。代表性地，证明了通过“点击”型环加成反应制备具有with，per和尼罗红的螺吡喃共轭物的共轭化学。这些分子二元化合物通过光谱学表征。