2-formyl-9,10-bis(1,3-dithiol-2-ylidene)dihydroanthracene | 194299-38-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-formyl-9,10-bis(1,3-dithiol-2-ylidene)dihydroanthracene
• 英文别名: 9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene-2-carbaldehyde；2-formyl-9,10-bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene；9,10-Bis(1,3-dithiol-2-ylidene)anthracene-2-carbaldehyde
• CAS: 194299-38-2
• 化学式: C₂₁H₁₂OS₄
• 分子量: 408.59
• InChiKey: JDOHRTISBFJDGD-UHFFFAOYSA-N

物化性质

• 沸点：
  592.6±50.0 °C(Predicted)
• 密度：
  1.538±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-formyl-9,10-bis(1,3-dithiol-2-ylidene)dihydroanthracene 在 哌啶 、 盐酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 水 、 丙酮 、 乙腈 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Rhodanine-3-acetic acid and π-extended tetrathiafulvalene (exTTF) based systems for dye-sensitized solar cells

  摘要：

  我们在此报告一系列基于 exTTF 的新型有机染料（3 和 7a,b）的合成、电化学和光物理性质及其在染料敏化太阳能电池（DSSC）中的应用。在这三种设计的染料中，电子捐赠者 exTTF 基团通过乙烯基或乙烯基噻吩间隔物与罗丹宁-3-乙酸电子受体单元相连。电化学研究表明，染料的 LUMO 层与 TiO2 传导带之间的能隙随着共轭体系长度的增加而减小。因此，用这些染料制造的有机 DSSC 的功率转换效率与其光收集能力成反比。

  DOI：

  10.1039/c4nj01261e
• 作为产物：
  描述：

  2-羟甲基蒽醌 在 盐酸 、 正丁基锂 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 61.0h， 生成 2-formyl-9,10-bis(1,3-dithiol-2-ylidene)dihydroanthracene
  参考文献：
  名称：

  Synthesis and Properties of the First Highly Conjugated Tetrathiafulvalene Analogues Covalently Attached to [60]Fullerene

  摘要：

  The synthesis of the first C-60-based donor-acceptor (D-A) systems (12a-c) in which the C-60 core is covalently linked to strong, highly conjugated pi-electron donors derived of tetrathiafulvalene (TTF) with p-quinodimethane structure has been carried out by cyclization with azomethine ylides following Prate's procedure. The synthetic strategy requires the preparation of the novel formyl-substituted pi-extended donors which, in turn, are prepared in a multistep synthetic procedure by reaction of 2-formyl-9,10-anthraquinone (6) with the appropriately substituted phosphonate esters (8). Semiempirical PM3 calculations predict a geometry highly distorted from planarity for the donor fragment and a most stable conformation in which both 1,3-dithiole rings are far away from the [60]fullerene surface. The redox properties were determined by cyclic voltammetry in solution and reveal the presence of four cathodically shifted reduction waves, relative to C-60 and corresponding to the C-60 core, and a two-electron single oxidation wave to form stable dication species of the pi-extended donor units. Magnetic susceptibility measurements clearly indicate a paramagnetic behavior in the solid state, and a remarkable conductivity is observed for these single component organic compounds.

  DOI：

  10.1021/jo970320+

文献信息

• Molecular Dyads and Triads Based on Phenothiazine and π‐Extended Tetrathiafulvalene Donors, Bis(terpyridine)ruthenium(II) Complexes, and Polyoxometalates
  作者：Kevin Barthelmes、Maria Sittig、Andreas Winter、Ulrich S. Schubert

  DOI：10.1002/ejic.201700626

  日期：2017.8.24

  straightforward and modular method for the preparation of donor–photosensitizer–acceptor systems, based on exTTF/PTZ-functionalized bis(terpyridine)RuII complex/POM conjugates, is shown. The electrochemical and photophysical properties were studied, and a donor-strength-dependent quenching of the bis(terpyridine)RuII-based emission was observed.

  显示了一种基于exTTF / PTZ-官能化的双（叔吡啶）Ru II复合物/ POM共轭物的直接，模块化的供体-光敏剂-受体系统的制备方法。研究了电化学和光物理性质，并观察到了双（叔吡啶）Ru II基发光的供体强度依赖性猝灭。
• Stabilisation of charge-separated states via gain of aromaticity and planarity of the donor moiety in C60-based dyads
  作者：Nazario Martín、Luis Sánchez、Dirk M. Guldi

  DOI：10.1039/a908770b

  日期：——

  The gain of aromaticity and planarity, associated with the oxidation of a π-extended TTF electron donor, is the key feature for obtaining strong stabilisation of photolytically generated radical pairs in novel C60-based dyads.

  芳香性和平面性的增加与 π 扩展 TTF 电子供体的氧化有关，是新型 C60 基二元化合物中光解产生的自由基对获得强力稳定的关键特征。
• Synthesis and properties of push–pull chromophores for second-order nonlinear optics derived from π-extended tetrathiafulvalenes (TTFs)
  作者：Manuel Otero、Ma Ángeles Herranz、Carlos Seoane、Nazario Martı́n、Javier Garı́n、Jesús Orduna、Rafael Alcalá、Belén Villacampa

  DOI：10.1016/s0040-4020(02)00803-7

  日期：2002.9

  (EFISH technique) studied. The redox properties of the novel compounds have been investigated by cyclic voltammetry (CV) and the CV data reveal the good donor ability of the exTTF unit. Although the energy of the intramolecular charge-transfer (ICT) band displayed by these compounds and their redox potentials are fairly insensitive to the nature of the conjugated spacer linking the donor and the acceptor

  通过π共轭低烯间隔基（14a – c – 16a – c）连接到对硝基苯基电子接受单元的新型π扩展四硫富瓦烯（exTTF）衍生物显示出良好的二阶光学非线性。寡烯间隔子的共轭长度和π共轭桥中噻吩环的存在（20a – c）已在理论上（PM3）和/或实验上（EFISH技术）进行了研究。已通过循环伏安法（CV）研究了新型化合物的氧化还原特性，并且CV数据显示了exTTF单元的良好供体能力。虽然这些化合物显示的分子内电荷转移（ICT）谱带的能量及其氧化还原电位对连接供体和受体部分的共轭间隔基的性质相当不敏感，但观察到其二阶非线性光学响应有所增加在增加共轭长度上。带有噻吩环的化合物20a – c具有出色的热稳定性，分解温度超过400°C。一系列新的D-π-A化合物（23a – c）还合成和研究了带有1，3-二硫醇-2-亚烷基供体单元的）。
• Probing Molecular Wires: Synthesis, Structural, and Electronic Study of Donor-Acceptor Assemblies Exhibiting Long-Range Electron Transfer
  作者：Francesco Giacalone、José L. Segura、Nazario Martín、Jeff Ramey、Dirk M. Guldi

  DOI：10.1002/chem.200500073

  日期：2005.8.5

  incorporating pi-conjugated oligo(phenylenevinylene) wires (oligo-PPV) of different length between pi-extended tetrathiafulvalene (exTTF) as electron donor and C60 as electron acceptor has been prepared by multistep convergent synthetic approaches. The electronic interactions between the three electroactive species present in 16-20 were investigated by UV-visible spectroscopy and cyclic voltammetry (CV)

  一系列供体-受体阵列（C60-oligo-PPV-exTTF; 16-20），在作为电子供体的pi延伸的四硫富富瓦烯（exTTF）和C60之间掺入了不同长度的pi共轭低聚（亚苯基乙烯撑）线（oligo-PPV）由于电子受体是通过多步收敛合成方法制备的。通过紫外可见光谱和循环伏安法（CV）研究了16-20中存在的三种电活性物质之间的电子相互作用。我们的研究清楚地表明，尽管C60单元通过pi共轭的寡聚PPV框架与exTTF供体相连，但在基态中未观察到明显的电子相互作用。有趣的是，在长达50埃的距离内进行光诱导的电子转移过程，可提供高度稳定的自由基离子对。对于光生成的电荷分离态，在苯甲腈中测得的寿命在数百纳秒（约500 ns）的范围内，与低聚物的长度（即，从单体到五聚体）无关。对于含七聚体的阵列，观察到不同的寿命（4.35微米）。寿命上的这种差异是由oPPV部分的平面度随线长增加而造成的，这是通
• New Vistas in Fullerene Chemistry: Organosulfur Compounds Expand the Performance Of Carbon Nanomaterials
  作者：Takeshi Akasaka、Takahiro Tsuchiya、Lai Feng、Yuta Takano、Shigeru Nagase

  DOI：10.1080/10426507.2012.736109

  日期：2013.4.1

  the introduced sulfur atoms promote active redox properties in the fullerene molecules. Complexation of La@C82 and unsaturated thiacrown ether, for instance, shows remarkable host–guest interaction and electron transfer to the fullerene. In contrast to these intermolecular electron-accepting properties of EMFs, intramolecular properties were revealed through studies of covalently bonded La2@C80 or La@C82

  摘要 将有机硫部分引入 EMF 是阐明 EMF 电子转移行为的成功方法，因为引入的硫原子促进了富勒烯分子的活性氧化还原性能。例如，La@C82 和不饱和噻冠醚的络合显示出显着的主客体相互作用和向富勒烯的电子转移。与 EMF 的这些分子间电子接受特性相反，通过对共价键合的 La2@C80 或 La@C82 和 π 扩展的四硫富瓦烯（exTTF）二元组的研究揭示了分子内特性。这些关于电子转移行为的第一个里程碑启发了我们确定并扩展我们对 EMF 独特特性的了解。这些发现表明 EMF 基于其独特的分子结构和作为新型碳纳米材料的电子和磁性的潜在应用。图形概要