1,4-bis((triisopropylsilyl)ethynyl)anthracene-2,3-diamine | 1334680-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4-bis((triisopropylsilyl)ethynyl)anthracene-2,3-diamine
• 英文别名: 1,4-bis[2-tri(propan-2-yl)silylethynyl]anthracene-2,3-diamine
• CAS: 1334680-34-0
• 化学式: C₃₆H₅₂N₂Si₂
• 分子量: 568.993
• InChiKey: PBTCXYQJTBBGEO-UHFFFAOYSA-N

物化性质

• 沸点：
  631.1±55.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-bis((triisopropylsilyl)ethynyl)anthracene-2,3-diamine 在 selenium(IV) oxide 作用下， 以 乙醇 、 水 为溶剂， 以74%的产率得到4,11-bis-[(triisopropylsilanyl)-ethynyl]-2-selena-1,3-diaza-cyclopenta[b]anthracene
  参考文献：
  名称：

  From Thia- to Selenadiazoles: Changing Interaction Priority

  摘要：

  The synthesis, optical, and electrochemical properties as well as solid-state structures of a series of alkynylated, benzannulated selenadiazoles are reported. This set of compounds Is compared to the lighter homologue series, the thiadiazoles. The selenadiazoles show head-to-head dimerization in the solid state, while packing of the thiadiazoles was dominated by the steric bulk of the side groups. The Se-N interaction is a supramolecular motif that should drive the effective self-assembly and modulate charge transport when these compounds are used as thin films in devices.

  DOI：

  10.1021/ol303490b
• 作为产物：
  描述：

  4,11-bis(triisopropylsilylethynyl)anthra[2,3-c]-[1,2,5]thiadiazole 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.58h， 生成 1,4-bis((triisopropylsilyl)ethynyl)anthracene-2,3-diamine
  参考文献：
  名称：

  From Thia- to Selenadiazoles: Changing Interaction Priority

  摘要：

  The synthesis, optical, and electrochemical properties as well as solid-state structures of a series of alkynylated, benzannulated selenadiazoles are reported. This set of compounds Is compared to the lighter homologue series, the thiadiazoles. The selenadiazoles show head-to-head dimerization in the solid state, while packing of the thiadiazoles was dominated by the steric bulk of the side groups. The Se-N interaction is a supramolecular motif that should drive the effective self-assembly and modulate charge transport when these compounds are used as thin films in devices.

  DOI：

  10.1021/ol303490b

文献信息

• Azaacenodibenzosuberones
  作者：Victor Brosius、Matthias Müller、Jan Borstelmann、Frank Rominger、Jan Freudenberg、Uwe H. F. Bunz

  DOI：10.1021/acs.joc.9b02756

  日期：2020.1.3

  N-heteroacenes was obtained by the condensation of dibenzosuberonetriketone with a series of substituted diamino- and tetramino-arenes. The electron-deficient triketone reacts at room temperature and furnishes the pyrazine or bis-pyrazine-containing condensation products in good to excellent yield. The targets all display negative curvature according to single crystal structures.

  通过使二苯并亚甲基三酮与一系列取代的二氨基-和四氨基-芳烃缩合获得一系列的二苯并亚砜基-稠合的N-杂蒽。缺电子的三酮在室温下反应，并以良好至极佳的产率提供含吡嗪或双吡嗪的缩合产物。靶都根据单晶结构显示负曲率。
• Synthesis and Characterization of Heterobenzenacyclo‐octaphanes Derived from Cyclotetrabenzoin
  作者：Sebastian Hahn、Maymounah Alrayyani、Anna Sontheim、Xiqu Wang、Frank Rominger、Ognjen Š. Miljanić、Uwe H. F. Bunz

  DOI：10.1002/chem.201701125

  日期：2017.8.4

  We describe the modular synthesis and characterization of several substituted N‐hetero benzenacyclooctaphanes (BAOs), a new motif for heteroaromatic conjugated macrocycles. The targets were synthesized via condensation of substituted aromatic ortho‐diamines with a cyclic octaketone building block in moderate to excellent yields (41–91 %). We evaluated the optical and electronic properties and the solid‐state

  我们描述了几种取代的N-杂合苯并环辛烷（BAOs）的模块化合成和表征，BAOs是杂芳族共轭大环化合物的新基序。目标是通过取代的芳族邻二胺与环状辛酮的缩合反应合成的，产率中等至优异（41-91％）。我们评估了靶的光学和电子性质以及固态结构，并通过与它们的线性二苯基N-杂并苯对应物进行比较来讨论了它们的性质。
• Substituted Tetraaza- and Hexaazahexacenes and their<i>N</i>,<i>N</i>′-Dihydro Derivatives: Syntheses, Properties, and Structures
  作者：Jens U. Engelhart、Benjamin D. Lindner、Manuel Schaffroth、David Schrempp、Olena Tverskoy、Uwe H. F. Bunz

  DOI：10.1002/chem.201500518

  日期：2015.5.26

  The palladium‐catalyzed coupling of a substituted o‐diaminoanthracene and a substituted o‐diaminophenazine to substituted 2,3‐dichloroquinoxalines furnishes 10 differently substituted N,N′‐dihydrotetraaza‐ or ‐hexaazahexacenes with the quinoxaline group of the azaacenes carrying fluorine, chlorine, or nitro groups. The N,N′‐dihydrotetraazahexacenes with hydrogen, chlorine, and fluorine subtituents are

  取代的邻二氨基蒽和取代的邻二氨基吩嗪在钯催化下与取代的2,3-二氯喹喔啉之间的偶合提供了10个不同取代的N，N'-二氢四氮杂或六氮杂六环烯，以及带有氟，氯，或硝基。的Ñ，Ñ '与氢，氯，和氟subtituents -dihydrotetraazahexacenes被氧化成azaacenes，而只有父Ñ，Ñ '-dihydrohexaazahexacenes，具有氢取代基，是由氧化的MnO 2。所得的氮杂并苯乙炔以其光学和光谱数据表征。此外，母体四氮杂六烯及其二氟取代衍生物也获得了单晶X射线结构。N，N'-二氢六氮杂十六碳烯的二氯和四氯衍生物也已进行了结构表征。
• Thiadiazolo‐Azaacenes
  作者：Matthias Müller、Silke Koser、Olena Tverskoy、Frank Rominger、Jan Freudenberg、Uwe H. F. Bunz

  DOI：10.1002/chem.201900462

  日期：2019.4.26

  This work reports the synthesis and characterization of bis‐ and tetrakis(thiadiazolo)‐appended di‐ and tetraazaacenes, displaying up to seven catenated benzene/pyrazine rings. The targets are obtained by condensation of benzo‐bis(thiadiazole)‐4,5‐dione with aromatic di‐ and tetraamines. The condensation products—up to a heptacene‐like species—are stable but can be insoluble. Soluble derivatives are

  这项工作报告了合成的双和四（噻二唑）-二氮杂和四氮杂并丁烯酮的合成和表征，显示出多达七个链状的苯/吡嗪环。通过苯并双（噻二唑）-4,5-二酮与芳族二胺和四胺的缩合获得目标。缩合产物（直至庚烷样物质）稳定，但不溶。可溶性衍生物易于加工，但不显示增强的电子亲合力，因为两个或四个连接的苯并噻二唑单元可有效地与并苯共振分离，从而最大程度地提高了Clar弹性体的数量。
• Azaarene Dimers
  作者：Sebastian Hahn、Julian Butscher、Qingzhi An、Angelina Jocic、Olena Tverskoy、Marcus Richter、Xinliang Feng、Frank Rominger、Yana Vaynzof、Uwe H. F. Bunz

  DOI：10.1002/chem.201901139

  日期：2019.5.28

  their absorption spectra remained very similar to those of the constituting monomers. The dimers displayed greatly reduced fluorescence when compared to the monomers, suggesting that there is a significant interaction of the two azarene units in the excited state. Preliminary investigations showed that the dimers are attractive for application as acceptors in organic photovoltaic because they significantly

  制备了Binaphthyl-3,3'，4,4'-四酮并与不同的双（TIPS-乙炔基）-取代的（TIPS =三异丙基硅烷）芳族二胺偶联，形成了二聚苯并-稠合的氮杂并烷单键。分子的两半相对于彼此高度扭曲，并且在基态下显示出有限的电子相互作用，因为它们的吸收光谱仍然与构成单体的吸收光谱非常相似。当与单体相比时，二聚体显示出大大降低的荧光，表明在激发态下，两个azarene单元之间存在显着的相互作用。初步研究表明，由于二聚体明显优于其单体对应物，因此在有机光伏中用作受体是很有吸引力的。