6-bromo-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione | 84216-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-bromo-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 4-bromo-N-phenyl-1,8-naphthalimide；6-bromo-2-phenylbenzo[de]isoquinoline-1,3-dione
• CAS: 84216-52-4
• 化学式: C₁₈H₁₀BrNO₂
• 分子量: 352.187
• InChiKey: UULQEVGDKCRBSJ-UHFFFAOYSA-N

物化性质

• 熔点：
  230-230.5 °C (sublm)(Solv: acetic acid (64-19-7); ethanol (64-17-5))
• 沸点：
  545.2±42.0 °C(Predicted)
• 密度：
  1.622±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  6-bromo-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione 在 aluminum oxide 、 氢碘酸 、 copper(II) sulfate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 37.0h， 生成 10-(4-methoxyphenyl)-5,10-diphenylbenzo-[de]pyrano[2,3-g]isoquinoline-4,6(5H,10H)-dione
  参考文献：
  名称：

  Synthesis and Photochromism of Naphthopyrans Bearing Naphthalimide Chromophore: Predominant Thermal Reversibility in Color-Fading and Fluorescence Switch

  摘要：

  Two novel photochromic naphthopyrans containing naphthalimide moieties (Nip1 and Nip2) were studied in solution under flash photolysis conditions, exhibiting highly photochromic response, rapid thermal bleaching rate and good fatigue-resistance. Owing to the different N-substituted imide groups at the naphthalimide units, the thermal bleaching rate of Nip2 bearing phenyl on the naphthalimide unit is found to be approximately 2 times that of Nip1 bearing n-butyl, indicating that the photochromic properties can be modulated with introduction of different functional groups on the naphthalimide unit. In Nip1 and Nip2, the strong electron-withdrawing effect of the imide group incorporated at the naphthalimide moiety maintains several merits: (i) shifting absorption bands to longer wavelength, (ii) beneficial to an enhancement in the ratio of transoid-cis (TC) isomer and an increase in the transformation rate from transoid-trans (TT) to TC with respect to reference compound NP, and (iii) resulting in a preferable color bleaching rate and fading absolutely to their colorless state with thermal reversibility. As demonstrated in the system of NP, the slow transformation process from TT to TC might be the predominant dynamic step in thermal back process, leading to the residual color of NP being only faded to its original colorless state by visible light irradiation. The optical densities of colored forms for Nip1 and Nip2 are dependent upon the intensity of incident light, ensuring a possible application in the manufacture of ophthalmic lenses and smart windows. Moreover, the fluorescence of Nip1 and Nip2 can be switched on and off by photoinduced conversion between the closed and open forms.

  DOI：

  10.1021/jp208082w
• 作为产物：
  描述：

  2-溴-1,8-萘酐 在 溶剂黄146 、 苯胺 作用下， 生成 6-bromo-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Fluorescent brighteners, methods of preparation thereof, fluorescent brightener compositions, and methods of preparation and uses thereof

  摘要：

  式(I)的化合物，其中R1、R2和R3在每次出现时独立地为氢、卤素、氰基、C1-C20脂肪基、C3-C10环脂肪基或C3-C20芳香基，但R1为甲基或氢时，R2和R3不为氢；R4和R5在每次出现时独立地为氢、卤素、氰基、C1-C20脂肪基、C3-C10环脂肪基或C3-C10芳香基；R7和R8在每次出现时独立地为卤素、氰基、C1-C20脂肪基、C3-C10环脂肪基或C3-C10芳香基；R6为C2-C20脂肪基、C3-C10环脂肪基或C3-C20芳香基；“n”和“m”分别独立地为0至3的整数。

  公开号：

  US20070117887A1

文献信息

• USE OF SUBSTITUTED PERYLENES IN ORGANIC SOLAR CELLS
  申请人：KÖNEMANN Martin

  公开号：US20110308592A1

  公开（公告）日：2011-12-22

  The present invention relates to an organic solar cell with a photoactive region which comprises at least one organic donor material in contact with at least one organic acceptor material, wherein the donor material and the acceptor material form a donor-acceptor heterojunction and wherein the photoactive region comprises at least one substituted perylene.

  本发明涉及一种有机太阳能电池，其具有包括至少一种有机给体材料与至少一种有机受体材料接触的光活性区域，其中给体材料和受体材料形成给体-受体异质结，且光活性区域包括至少一种取代的苝。
• TERRYLENE COMPOUNDS, PREPARATION THEREOF AND USE THEREOF IN ORGANIC SOLAR CELLS
  申请人：Könemann Martin

  公开号：US20120234380A1

  公开（公告）日：2012-09-20

  A terrylene compound of formula I: wherein R 1 to R 4 are each independently an unsubstituted or substituted alkyl, aryl, thiophenyl or oligothiophenyl group, or a hydrogen atom. Two adjacent radicals selected from R 1 to R 4 , together with the carbon atoms of the benzene ring to which they are bonded, may also form a fused ring system having 1 to 8 additional rings. With the carbon atoms to which it is bonded, A forms a fused monocyclic, dicyclic, tricyclic, tetracyclic, pentacyclic or hexacyclic ring system which optionally contains one or more independently selected substituents. A process for preparing the terrylene compound. An organic solar cell with a photoactive region including at least one organic donor material in contact with at least one organic acceptor material, the donor material and the acceptor material forming a donor-acceptor heterojunction, and the photoactive region including at least one such terrylene compound.

  公式I的苯基化合物：其中R1至R4分别独立地是未取代或取代的烷基、芳基、噻吩基或寡噻吩基，或氢原子。从R1至R4中选择的相邻基团，与它们结合的苯环的碳原子一起，也可以形成具有1至8个额外环的融合环系统。与它结合的碳原子一起，A形成一个融合的单环、双环、三环、四环、五环或六环系统，该系统可以选择性地包含一个或多个独立选择的取代基。一种制备苯基化合物的方法。一种有机太阳能电池，其光活性区域包括至少一种有机给体材料与至少一种有机受体材料接触，给体材料和受体材料形成给受体异质结，光活性区域包括至少一种这样的苯基化合物。
• FLUORESCENT BRIGHTENERS, METHODS OF PREPARATION THEREOF, FLUORESCENT BRIGHTENER COMPOSITIONS, AND METHODS OF PREPARATION AND USES THEREOF
  申请人：Naik Shantaram Narayan

  公开号：US20110065843A1

  公开（公告）日：2011-03-17

  A compound of Formula (I) wherein R 1 , R 2 , and R 3 are independently at each occurrence hydrogen, a halogen, a cyano functionality, a C 1 -C 20 aliphatic functionality, a C 3 -C 10 cycloaliphatic functionality or a C 3 -C 20 aromatic functionality, with the proviso that R 2 and R 3 are not hydrogen when R 1 is a methyl or hydrogen; R 4 and R 5 are independently at each occurrence hydrogen, a halogen, a cyano functionality, a C 1 -C 20 aliphatic functionality, a C 3 -C 10 cycloaliphatic functionality or a C 3 -C 10 aromatic functionality; R 7 and R 8 are independently at each occurrence, a halogen, a cyano functionality, a C 1 -C 20 aliphatic functionality, a C 3 -C 10 cycloaliphatic functionality or a C 3 -C 10 aromatic functionality; R 6 is a C 2 -C 20 aliphatic functionality, a C 3 -C 10 cycloaliphatic functionality or a C 3 -C 20 aromatic functionality; and “n” and “m” are each independently integers having a value of 0 to 3.

  化合物的化学式（I），其中R1、R2和R3在每次出现时独立地为氢、卤素、氰基、C1-C20脂肪基、C3-C10环脂肪基或C3-C20芳香基，但R1为甲基或氢时，R2和R3不为氢；R4和R5在每次出现时独立地为氢、卤素、氰基、C1-C20脂肪基、C3-C10环脂肪基或C3-C10芳香基；R7和R8在每次出现时独立地为卤素、氰基、C1-C20脂肪基、C3-C10环脂肪基或C3-C10芳香基；R6为C2-C20脂肪基、C3-C10环脂肪基或C3-C20芳香基；“n”和“m”分别独立地为0至3的整数。
• Synthesis and photophysical properties of blue-emitting fluorescence dyes derived from naphthalimide derivatives containing a diacetylene linkage group
  作者：Kyung-Won Kim、Geun-Hyeong Kim、Su-Hyeon Kwon、Hyo-In Yoon、Jung-Eek Son、Jae-Hong Choi

  DOI：10.1016/j.dyepig.2018.05.065

  日期：2018.11

  films was examined. N-Phenyl groups were found to have a greater effect on the fluorescence of naphthalimide-based dyes than analogue containing an N-alkyl group. In addition, investigation of the effect of diacetylene linkages at the 3- or 4-positions of naphthalimide-based dyes showed that the fluorescence was influenced by the electron-donating effect of the diacetylene linkage which could afford

  合成了四种在3或4位具有二乙炔键的萘二甲酰亚胺基染料，以改善荧光染料的热稳定性以及蓝色区域的荧光发射效率。还研究了合成染料的吸收和荧光性质。使用密度泛函理论和随时间变化的密度泛函理论，使用高斯09对所制备染料的几何形状和分子轨道进行了模拟。此外，还研究了染料在光转换膜中的适用性。发现N-苯基对萘二甲酰亚胺基染料的荧光的影响大于含N的类似物。-烷基。此外，对基于萘二甲酰亚胺的染料在3或4位上的二乙炔键的影响的研究表明，荧光受二乙炔键的电子给体作用的影响，该作用可以使染料的π轨道更多地共轭。 。合成了四种来自具有联乙炔键的1,8-萘二甲酰亚胺的蓝色荧光染料，然后将其涂覆在PE膜中。使用密度泛函理论（DFT）计算分析光物理性质，并在理论上以B3LYP / 6-31G的水平模拟了染料从最高占据分子轨道（HOMOs）到最低未占据分子轨道（LUMOs）的激发。高斯09程序套件。使用这些方法，对乙炔基键，烷基，
• 2‐Azaallyl Anions as Light‐Tunable Super‐Electron‐Donors: Coupling with Aryl Fluorides, Chlorides, and Bromides
  作者：Qianmei Wang、Michal Poznik、Minyan Li、Patrick J. Walsh、Jason J. Chruma

  DOI：10.1002/adsc.201800396

  日期：2018.8.6

  of reducing a collection of aryl halides via a single electron transfer and coupling with the corresponding radicals to forge new C−C bonds. This offers a robust approach for the arylation of 2‐azaallyls. Mechanistic studies demonstrate that the reactions proceed via either a radical pathway for aryl bromides and chlorides or a SNAr mechanism for activated aryl fluorides. Moreover, we demonstrate that

  在本文中，我们将2-氮杂烯丙基阴离子作为有色超电子给体，能够通过单次电子转移并与相应的自由基偶联形成新的C-C键，从而减少卤代芳基的收集。这为2-氮杂烯丙基的芳基化提供了一种可靠的方法。机制研究表明，该反应通过任一为芳基溴化物和氯化物或A S自由基途径进行Ñ活化芳基氟化物的Ar机制。此外，我们证明了可见光对有色2-氮杂烯丙基阴离子的照射可以进一步扩展其还原能力，从而使自由基介导的偶合反应与原本不反应的富电子芳基卤化物结合。获得了高达94％的分离收率，总的相关性和实用性通过已知药剂和流行的荧光团的衍生化得到证明。