6-bromo-N-phenylnaphthalen-2-amine | 202831-66-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-bromo-N-phenylnaphthalen-2-amine
• CAS: 202831-66-1
• 化学式: C₁₆H₁₂BrN
• 分子量: 298.182
• InChiKey: RIHHTXUAXIWXGS-UHFFFAOYSA-N

物化性质

• 熔点：
  126 °C
• 沸点：
  442.3±20.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-bromo-N-phenylnaphthalen-2-amine 在 4-二甲氨基吡啶 、 potassium phosphate 、 二氯化双(三环己基膦)镍(II) 、 palladium diacetate 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 36.03h， 生成 2,6-diphenylnaphthalene
  参考文献：
  名称：

  镍催化的Boc活化的芳香胺的Kumada偶联通过非定向选择性芳基C–N键的裂解。

  摘要：

  通过在温和的反应条件下选择性裂解芳基C–N键，开发了镍催化的苯胺衍生物的Kumada偶联。没有在苯胺上预先安装邻位导向基团，Boc保护的芳族胺与芳基格氏试剂的交叉偶联反应提供了不对称的联芳基。通过DFT计算进行的机理研究表明，镍介导的C–N键裂解是限速步骤。

  DOI：

  10.1021/acs.orglett.9b00242
• 作为产物：
  描述：

  6-溴-2-萘酚 、 苯胺 在 对甲苯磺酸 作用下， 以80%的产率得到6-bromo-N-phenylnaphthalen-2-amine
  参考文献：
  名称：

  三重态激子的同时收获在双方宾主材料的OLED与分子内电荷转移功能通过三重态湮灭†

  摘要：

  具有分子内电荷转移（ICT）特征的红色萘二甲酰亚胺衍生物，即（E）-2-（4-（叔丁基）苯基）-6-（2-（6-（二苯基氨基）萘-2-基）设计并合成了乙烯基）-1 H-苯并[ de ]异喹啉-1,3（2 H）-二酮（NA-TNA）。光物理和磁电致发光（MEL）表征结果表明，由于存在较低的三重态激发态，NA-TNA可以通过三重态-三重态an灭（TTA）过程在有机发光二极管（OLED）中收获三重态激子。具有3个ππ*字符。因此，使用NA-TNA作为客体化合物和CzPhONI（另一种具有ICT功能的具有三重态融合延迟荧光（TFDF）特性的ICT的萘酰亚胺衍生物）作为主体材料，获得了一种高性能橙色OLED，其具有6 wt％的NA-TNA掺杂的CzPhONI膜作为发光层。最大电流效率（LE最大），亮度（大号最大值），和外部量子效率（EQE最大此OLED的）是7.73光盘-1，31 940 CD米-2和5

  DOI：

  10.1039/c5tc00779h

文献信息

• Benzothiazole-containing two-photon chromophores exhibiting strong
  申请人：The United States of America as represented by the Secretary of the Air

  公开号：US06100405A1

  公开（公告）日：2000-08-08

  There are provided asymmetrical two-photon chromophores of the formula: D--Ar--A wherein Ar is selected from the group consisting of ##STR1## wherein Fl is a fluorene group of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are alkyl groups having 2 to 20 carbon atoms, and wherein R.sub.1 and R.sub.2 are the same or different; wherein D is ##STR3## wherein Q is selected from the group consisting of --H, --OH and --O--C.sub.x H.sub.2x+1, wherein x has a value of 1 to 10; and wherein A is selected from the group consisting of ##STR4## wherein Z is selected from the group consisting of --O-- and --S--.

  提供了公式为：D--Ar--A 的非对称双光子色团，其中 Ar 选自以下组合：##STR1## 其中 Fl 是公式为：##STR2## 的芴基团，其中 R1 和 R2 是碳原子数为 2 到 20 的烷基基团，且 R1 和 R2 可相同也可不同；其中 D 是 ##STR3## 其中 Q 选自以下组合：--H、--OH 和 --O--C x H 2x+1，其中 x 取值为 1 到 10；A 选自以下组合：##STR4## 其中 Z 选自以下组合：--O-- 和 --S--。
• Structure–property relationship of naphthalene based donor–π–acceptor organic dyes for dye-sensitized solar cells: remarkable improvement of open-circuit photovoltage
  作者：Fan Yang、Md. Akhtaruzzaman、Ashraful Islam、Tienan Jin、Ahmed El-Shafei、Chuanjiang Qin、Liyuan Han、Khalid A. Alamry、Samia A. Kosa、Mahmoud A. Hussein、Abdullah Mohamed Asiri、Yoshinori Yamamoto

  DOI：10.1039/c2jm34363k

  日期：——

  Four new donor–π–acceptor organic dyes (YF01–04), containing naphthalene-substituted amines as an electron donor and cyanoacrylic acid as an electron acceptor, were designed and synthesized, and their photophysical properties and dye-sensitized solar cells (DSCs) performances were characterized. Dyes YF02 and YF04, with 2,6-disubstituted naphthalene frameworks, were superior than their analog dyes YF03 and YF01, having 1,2-disubstituted naphthalene moiety, in incident-photo-to-current conversion efficiency (IPCE) and total solar-to-electric conversion efficiency (η). The DSCs based on YF02, comprised of diphenylamine moiety as the donor, produced the highest η of 5.29% compared to 4.03% of the analog dye YF04, which has pyrrolidine as the donor. Remarkably, a high open-circuit photovoltage (Voc) of 0.799–0.807 V was achieved in the cases of YF02–03, which have diphenylamine-donors. To better understand the structure–property relationship for DSCs application, molecular modelling was performed on YF01–04 and vertical electronic excitations were calculated using long-range corrected energy functional WB97XD and CAM-B3LYP at the basis set level DGDZVP, which were in excellent agreement with the experimental results. Moreover, the equilibrium molecular geometries of dyes YF01–04 were calculated at the density function theory (DFT) level using the hybrid energy functional B3LYP and basis set DGDZVP. The torsion angles (θ) between the naphthalene moiety and diphenylamine donor in YF02 and YF03 were more twisted than that of the pyrrolidine-donor dyes YF01 and YF04, precluding efficient intermolecular π–π charge transfer, which translated into high Voc. Compared to the reference dye TA-St-CA, which is based on diphenylamine as an electron donor linked to a phenyl ring, YF02 achieved higher Voc, which indicated that naphthalene substituted with diphenylamine is more efficient in retarding charge recombinations.

  设计并合成了四种新的供体-π-受体有机染料（YF01–04），这些染料以含有萘取代胺的化合物作为电子供体，以氰基丙烯酸作为电子受体，并对其光物理性质及染料敏化太阳能电池（DSCs）的性能进行了表征。具有2,6-二取代萘框架的染料YF02和YF04在入射光电流转换效率（IPCE）和总太阳能转电效率（η）方面优于其类似染料YF03和YF01，后者具有1,2-二取代萘基团。基于YF02的DSC，其供体为二苯胺基团，显示出5.29%的最高η，而类似染料YF04（供体为哌咯啶）的η为4.03%。在具有二苯胺供体的YF02和YF03中，惊人地达到了0.799–0.807 V的高开路光电压（Voc）。为了更好地理解DSC应用中的结构-性质关系，对YF01–04进行了分子建模，并使用长程修正的能量泛函WB97XD和CAM-B3LYP在DGDZVP基组水平上计算了垂直电子激发，这与实验结果非常一致。此外，使用混合能量泛函B3LYP和DGDZVP基组在密度泛函理论（DFT）水平上计算了染料YF01–04的平衡分子几何结构。YF02和YF03中萘基与二苯胺供体之间的扭转角（θ）比YF01和YF04（哌咯啶供体染料）的扭转角更大，从而阻碍了高效的分子间π-π电荷转移，导致高Voc。与参考染料TA-St-CA相比，该染料以二苯胺作为电子供体与苯环连接，YF02实现了更高的Voc，这表明用二苯胺取代的萘在延缓电荷复合方面更为有效。
• Nucleophilic <i>ipso</i>-Substitution of Aryl Methyl Ethers through Aryl C–OMe Bond Cleavage; Access to Functionalized Bisthiophenes
  作者：Abhishek Kumar Mishra、Ajay Verma、Srijit Biswas

  DOI：10.1021/acs.joc.6b02701

  日期：2017.4.7

  A metal and solvent free strategy to functionalize aryl methyl ethers through direct nucleophilic substitution of aryl C–OMe bond has been described. A wide range of O, S, N, and C-centered uncharged nucleophiles has been successfully employed. Using this protocol, functional derivatives of bisthiophene have been synthesized in a straightforward way. The reactions are highly atom-efficient and generate

  已经描述了通过芳基C–OMe键的直接亲核取代来实现芳基甲基醚官能化的无金属和无溶剂策略。已经成功地采用了各种以O，S，N和C为中心的不带电亲核试剂。使用该协议，已经以简单的方式合成了双噻吩的功能性衍生物。该反应是高度原子效率的，并且产生甲醇作为唯一的副产物。
• B(C₆F₅)₃-catalyzed metal-free hydrogenation of naphthylamines
  作者：Gen Li、Yongbing Liu、Haifeng Du

  DOI：10.1039/c5ob00009b

  日期：——

  A catalytic metal-free hydrogenation of naphthylamines using B(C6F5)3 as a catalyst was successfully achieved under mild conditions for the first time to furnish a variety of tetrahydronaphthylamines in 88–99% yields.

  使用B（C 6 F 5）3作为催化剂的萘胺的无催化金属氢化首次在温和条件下成功实现，以88-99％的产率提供了各种四氢萘胺。
• AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENCE DEVICE USING THE SAME
  申请人：Kawamura Masahiro

  公开号：US20080076942A1

  公开（公告）日：2008-03-27

  An aromatic amine derivative having a specific structure. An organic electroluminescence device which is composed of one or more organic thin film layers including at least one light emitting layer sandwiched between a cathode and an anode, wherein at least one of the organic thin film layers contains the aromatic amine derivative or a material for the organic electroluminescence device singly or as its mixture component. They provide an organic electroluminescence device with an enhanced efficiency of light emission and having prolonged lifetime emitting blue light, a novel aromatic amine derivative and a material for the organic electroluminescence device realizing the device.

  具有特定结构的芳香胺衍生物。一种有机电致发光器件，由至少包括一个发光层的一个或多个有机薄膜层组成，该发光层夹在阴极和阳极之间，其中至少一个有机薄膜层包含芳香胺衍生物或有机电致发光器件的材料，单独或作为其混合成分。它们提供了一种具有增强发光效率并具有长寿命的发出蓝光的有机电致发光器件，一种新颖的芳香胺衍生物和一种实现该器件的有机电致发光器件材料。