2-(10-(thiophen-2-yl)anthracen-9-yl)thiophene | 236392-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(10-(thiophen-2-yl)anthracen-9-yl)thiophene
• 英文别名: 9,10-bis(thiophen-2-yl)anthracene；9,10-di(thiophene-2-yl)anthracene；9,10-di(thiophen-2-yl)anthracene；9,10-bis(2-thienyl)anthracene；9,10-di(thien-2-yl)anthracene；9,10-dithienylanthracene；2-(10-thiophen-2-ylanthracen-9-yl)thiophene
• CAS: 236392-64-6
• 化学式: C₂₂H₁₄S₂
• 分子量: 342.485
• InChiKey: QZKSNIRTMFAUSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(10-(thiophen-2-yl)anthracen-9-yl)thiophene 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 24.0h， 生成 9,10-bis(5'-hexyl-[2,2'-bithiophen]-5-yl)anthracene
  参考文献：
  名称：

  Synthesis by MW-assisted direct arylation, side-arms driven self-assembly and functional properties of 9,10-dithienylanthracene orthogonal materials

  摘要：

  We report a new class of multifunctional 9,10-dithienylanthracene-based materials having an anthracene pi-core functionalized at the 9,10 positions with thienyl side-arms of different size and type of substitution. MW-assisted double direct arylation reaction is employed for the first time to synthesize the target molecules in one-step, organometallic free conditions, in only 5 min and yields up to 80% rather than by a multi-step Stile coupling taken as conventional reference approach. DFT calculations reveal a molecular conformation characterized by the thienyl rings orthogonal to the anthracene core. Nevertheless, despite the non-coplanar structure, all compounds exhibited highly crystalline cast films emitting blue light, with an extraordinary variability in morphology and hole mobility up to 8x10(-3) cm(2) V-1 s(-1). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.010
• 作为产物：
  描述：

  9,10-dihydroanthracene-9,10-dithienyl-9,10-diol 在 sodium dihydrogenphosphate 、 potassium iodide 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以90%的产率得到2-(10-(thiophen-2-yl)anthracen-9-yl)thiophene
  参考文献：
  名称：

  9,10-二芳基-9,10-二氢蒽-9,10-二醇的新型酸催化重排，得到10,10'-二芳基-9-蒽

  摘要：

  通常，可以通过在乙酸中用KI / NaH 2 PO 2还原相应的9,10-二芳基-9,10-二氢蒽-9,10-二醇来获得9,10-二芳基蒽。相反，我们发现，在杂芳基芳基取代基的情况下，并且当蒽取代基上存在per取代基时，会形成大量的蒽酮。可以认为这些蒽酮是由最初的二醇的频哪醇重新排列而产生的。据我们所知，这种类型的重排很少观察到，并且以这种方式获得的10,10'-二芳基-9-蒽酮很难用其他方法制备。我们制备了许多此类化合物，并研究了涉及的转化机理。结果与桥接过渡状态一致10。

  DOI：

  10.1016/s0040-4020(99)00406-8

文献信息

• Synthesis of Annulated Arenes and Heteroarenes by Hydriodic Acid and Red Phosphorus Mediated Reductive Cyclization of 2-(Hetero)aroylbenzoic Acids or 3-(Hetero)arylphthalides
  作者：Arasambattu Mohanakrishnan、Settu Rafiq

  DOI：10.1055/s-0036-1588337

  日期：——

  Annulated arenes and hetarenes were prepared in good to very good yields by hydriodic acid/red phosphorus mediated reductive cyclization of 3-(hetero)aryl phthalides. The reductive cyclization also proceeded successfully with 2-aroylbenzoic acids and 2-aroylnaphthoic acids.

  通过氢碘酸/红磷介导的 3-（杂）芳基苯酞的还原环化，以良好到非常好的产率制备了环化芳烃和杂环芳烃。2-芳酰基苯甲酸和2-芳酰基萘甲酸也成功地进行了还原环化。
• Linkage position influences of anthracene and tricyanovinyl groups on the opto-electrical and photovoltaic properties of anthracene-based organic small molecules
  作者：Vellaiappillai Tamilavan、Myungkwan Song、Rajalingam Agneeswari、Myung Ho Hyun

  DOI：10.1016/j.tet.2013.12.079

  日期：2014.2

  Anthracene-based small molecules incorporating an electron accepting tricyanovinyl (TCV) group was prepared to investigate the linkage position influences of the anthracene and TCV groups on the opto-electrical and photovoltaic properties of the molecules. The maximum absorptions of the anthracene-based molecules incorporating the TCV group at the phenyl group of the triphenylamine unit (TCV-TpaA9

  蒽基的小分子结合了电子接受三氰基乙烯基（TCV）的制备是为了研究蒽和TCV基团的键合位置对分子的光电和光伏性能的影响。在三苯胺单元的苯基上（TCV-TpaA 9,10 T，TCV-TpaTA 9,10 T和TCV-TpaA 2,6 T）或在噻吩单位（TpaA 9,10 T-TCV，TpaTA 9,10 T-TCV和TpaA 2,6 T-TCV被发现取决于蒽单元的连接位置。在三苯胺单元的苯基上含有TCV基团的分子的HOMO能级比在噻吩单元上的含有TCV基团的分子的HOMO能级高。溶液处理的小分子有机太阳能电池（SMOSC）具有ITO / PEDOT：PSS / TCV-TpaA 9,10 T或TCV-TpaA 2,6 T或TpaA 2,6 T-TCV：PC 71 BM（在AM 1.5辐照（100 mW cm -2）下，2：1 wt％）/ LiF / Al的最大能量转换效率分别为1.04％，1
• Lewis Acid/Brönsted Acid Mediated Benz-Annulation of Thiophenes and Electron-Rich Arenes
  作者：Settu Muhamad Rafiq、Ramakrishnan Sivasakthikumaran、Arasambattu K Mohanakrishnan

  DOI：10.1021/ol501006t

  日期：2014.5.16

  A facile preparation of benz-annulated heterocycles were achieved at rt involving a Lewis acid/Brönsted acid mediated annulation of heterocycles using 2,5-dimethoxytetrahydrofuran as a four-carbon synthon. The benz-/naphth-annulation was found to be successful with electron-rich arenes as well.

  在室温下，使用2，5-二甲氧基四氢呋喃作为四碳合成子，在路易斯酸/布朗斯台德酸介导的杂环环化中，实现了苯环式杂环的简便制备。还发现富电子芳烃也能成功实现苯并/萘环化。
• Effect of thiophene substitution on the intersystem crossing of arene photosensitizers
  作者：Farhan Sadiq、Jianzhang Zhao、Mushraf Hussain、Zhijia Wang

  DOI：10.1039/c8pp00230d

  日期：2018.11

  transient absorption spectra indicate the formation of a triplet state, the triplet state lifetime is up to 282 μs, and the singlet oxygen quantum yields (ΦΔ) are up to 60%. DFT/TDDFT computations indicate that introducing the thienyl substituent alters the relative singlet/triplet excited state energy levels, and the energy level-matched S1/T2 states are responsible for the enhanced ISC of the thienyl

  使用稳态和时间分辨的瞬态吸收和发射光谱，以及DFT / TDDFT计算，研究了噻吩基取代对几种芳烃的系统间穿越（ISC）的影响。我们发现，苯基和噻吩基取代基通常会引起发色团的红移吸收，并且DFT / TDDFT计算表明，红移的吸收和发射是由于HOMO增加和LUMO能级降低。纳秒瞬态吸收光谱表明三重态的形成，三重态寿命为至多282微秒，和单线态氧量子产率（Φ Δ）高达60％。DFT / TDDFT计算表明，引入噻吩基取代基会改变相对的单重态/三重态激发态能级，并且能级匹配的S 1 / T 2态是噻吩基化合物增强的ISC的原因。该信息对于设计无重原子的三重态光敏剂和研究有机化合物的基本光化学是有用的。
• Synthesis of Symmetrical and Unsymmetrical 9,10-Diarylanthracene Derivatives via Bis-Suzuki-Miyaura Cross-Coupling Reaction
  作者：Sambasivarao Kotha、Arun Kumar Ghosh、Kodand Dinkar Deodhar

  DOI：10.1055/s-2004-815981

  日期：——

  Synthesis of various 9,10-diarylanthracene derivatives via bis-Suzuki-Miyaura cross-coupling reaction as a key step is described. Availability of the 9,10-dithienylanthracenes derivatives where the thiophene unit is present in the molecule (e. g. 11, 12, 14) may provide an easy access to novel polymer and/or dendrimer preparation. In addition, we have synthesized unsymmetrical 9,10-diarylanthracene derivatives 20-25 by the Suzuki-Miyaura cross-coupling reaction, which are difficult to prepare by other transition metal-catalyzed cross-coupling reactions.

  描述了通过双-Suzuki-Miyaura交叉偶联反应作为关键步骤合成各种9,10-二芳基蒽衍生物。分子中存在噻吩单元的9，10-二噻吩基蒽衍生物(例如11、12、14)的可用性可以提供一种容易获得新型聚合物和/或树枝状聚合物的制备方法。此外，我们还通过Suzuki-Miyaura交叉偶联反应合成了其他过渡金属催化交叉偶联反应难以制备的不对称9,10-二芳基蒽衍生物20-25。