10-(1,3-dithiol-2-ylidene)anthracene-9(10)H-one | 109857-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 10-(1,3-dithiol-2-ylidene)anthracene-9(10)H-one
• 英文别名: 10-(2H-1,3-Dithiol-2-ylidene)anthracen-9(10H)-one；10-(1,3-dithiol-2-ylidene)anthracen-9-one
• CAS: 109857-93-4
• 化学式: C₁₇H₁₀OS₂
• 分子量: 294.398
• InChiKey: ZGMISWGWQICUBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  468.7±45.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  10-(1,3-dithiol-2-ylidene)anthracene-9(10)H-one 在 正丁基锂 作用下， 以 乙腈 为溶剂， 反应 13.5h， 生成 9-(1,3-Dithiol-2-ylidene)-10-(4,5-dimethyl-1,3-dithiol-2-ylidene)-9,10-dihydroanthracene - 7,7,8,8-Tetracycno-p-quinodimethane complex
  参考文献：
  名称：

  Moore, Adrian J.; Bryce, Martin R., Journal of the Chemical Society. Perkin transactions I, 1991, # 1, p. 157 - 168

  摘要：

  DOI：
• 作为产物：
  描述：

  10-(1,3-Dithiolan-2-yliden)anthron-S-oxid 在 碘代三甲硅烷 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到10-(1,3-dithiol-2-ylidene)anthracene-9(10)H-one
  参考文献：
  名称：

  One-Pot Synthesis of 4,5-Unsubstituted 1,3-Dithioles and 2-Alkylidene-1,3-dithioles from 1,3-DithiolaneS-Oxides

  摘要：

  报告中介绍了通过碘三甲基硅烷和二异丙基乙胺（许尼格碱）对相应的 1,3-二硫环戊烷 S-氧化物进行形式脱水，从而高效合成标题化合物的方法。

  DOI：

  10.1055/s-1990-26849

文献信息

• Conjugated and Cross-Conjugatedπ-Extended Cycloproparenes with Dithiole and Cyclopentadiene Functionality
  作者：Brian Halton、Carissa S. Jones

  DOI：10.1002/ejoc.200300619

  日期：2004.1

  dithiole-containing ketones with 1,1-bis(trimethylsilyl)cyclopropa[b]naphthalene 10 gives the π-extended cycloproparenes 27 and 29 in Peterson olefinations that are more efficient than Wittig−Horner reactions of cyclopropanthraquinone 31 with dithiolate 24 to give the cross-conjugated cycloproparenes 34 and 35. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  已将二硫醇和环戊二烯环引入官能化的环丙 [b] 萘中，以提供具有不同稳定性的高度着色、共轭和交叉共轭 π 扩展衍生物。含环戊二烯基的环丙萘 18 及其二硫亚丙基类似物 25 由溴苯基环丙萘 12 制备，1,1-双环戊二烯亚基 20 由二溴化物 13 制备。 使用含二硫醇的酮与 1,1-双（三甲基二甲硅烷基）邻苯二甲萘基） Peterson 烯化中的 π 扩展环丙芳烃 27 和 29 比环丙蒽醌 31 与二硫醇盐 24 的 Wittig-Horner 反应更有效，得到交叉共轭的环丙芳烃 34 和 35。（© Wiley-VCH Verlag GmbH & Co. KGaA，69德国魏因海姆，2004）
• Unsymmetrical and highly-conjugated tetrathiafulvalene and selenatrithiafulvalene derivatives: synthesis and reactions of novel heterocyclic Wittig–Horner reagents
  作者：Martin R. Bryce、Adrian J. Moore、Dominique Lorcy、Ajaib S. Dhindsa、Albert Robert

  DOI：10.1039/c39900000470

  日期：——

  Novel 1,3-dithiole and 1-selena-3-thiole Wittig–Homer reagents have been developed and used in the efficient synthesis of a range of new, unsymmetrical tetrathiafulvalene and selenatrithiafulvalene derivatives (6)–(10) and (16); cyclic voltammetry establishes that these molecules are efficient π-donors.

  已经开发了新型的1,3-二硫醇和1-selena-3-硫醇Wittig-Homer试剂，并将其用于有效合成一系列新的不对称四硫富瓦烯和硒三硫富瓦烯衍生物（6）-（10）和（16）；循环伏安法证实这些分子是有效的π供体。
• Self-Assembled Cofacial Zinc-Porphyrin Supramolecular Nanocapsules as Tuneable ¹ O₂ Photosensitizers
  作者：Cédric Colomban、Carles Fuertes-Espinosa、Sébastien Goeb、Marc Sallé、Miquel Costas、Lluís Blancafort、Xavi Ribas

  DOI：10.1002/chem.201705531

  日期：2018.3.20

  1O2 generation at the Zn–porphyrin centers. The PdII‐based prism is a particularly robust photosensitizer, whereas the CuII self‐assembled prism is a dormant photosensitizer that could be switched to a ON state upon disassembly of the suprastructure. Furthermore, the well‐defined cavity within the prisms allowed encapsulation of pyridine‐based ligands and fullerene derivatives, which led to a remarkable

  我们证明了在协调驱动的自组装棱镜中使用界面锌卟啉作为结构合成子来生产具有可调性质的笼状单线态氧（1 O 2）光敏剂的好处。特别是，我们描述了基于钯和铜的超分子胶囊的光敏性和发射特性，并证明了在这些离散的自组装棱镜中桥接金属节点的性质强烈影响了锌卟啉中心的1 O 2生成。基于Pd II的棱镜是一种特别坚固的光敏剂，而Cu II自组装棱镜是一种休眠型光敏剂，在拆卸上部结构时可以将其切换为“开”状态。此外，棱柱内明确界定的空腔允许封装吡啶基配体和富勒烯衍生物，这导致1 O 2产量的显着客体调节。
• Donor–π-Acceptor Species Derived from Functionalised 1,3-Dithiol-2-ylidene Anthracene Donor Units Exhibiting Photoinduced Electron Transfer Properties: Spectroscopic, Electrochemical, X-Ray Crystallographic and Theoretical Studies
  作者：Andrei S. Batsanov、Martin R. Bryce、Malcolm A. Coffin、Andrew Green、Ronald E. Hester、Judith A. K. Howard、Igor K. Lednev、Nazario Martín、Adrian J. Moore、John N. Moore、Enrique Ortí、Luis Sánchez、María Savirón、Pedro M. Viruela、Rafael Viruela、Tian-Qing Ye

  DOI：10.1002/(sici)1521-3765(19981204)4:12<2580::aid-chem2580>3.3.co;2-#

  日期：1998.12.4

  Novel single-component donor- acceptor species 7 and 8 have been synthesised from substituted 10-(1,3-dithiol-2-ylidene)anthracen-9(10H)one 6 by reaction with Lehnert's reagent and with N,N'-bis(trimethylsilyl)carbodiimide, respectively. The steady-state UV/visible spectra of these systems contain a solvatochromic band arising from intramolecular charge transfer between the donor and acceptor groups Ultrafast time-resolved spectroscopy shows that the excited state formed on photolysis has a lifetime of 170-400 ps, which depends strongly on solvent polarity. Cyclic voltammetric data indicate the presence of two active redox centres in the molecules: electrochemical oxidation and reduction form cation radicals and anion radicals, respectively. The X-ray crystal structures of compounds 6a, 7b and 11a reveal that all three molecules are severely distorted from planarity, with the central ring of the anthracenediylidene moiety adopting a boat conformation. The molecular structures of 6, 7 and 11 have been investigated theoretically at the ab initio 6-31G* level. Calculated geometries are in good agreement with the X-ray data and clearly show the decrease in steric hindrance along the series 11>7>8>6. The calculations support the intramolecular charge-transfer nature of the lowest energy absorption band observed for 6, 7 and 8, and explain the origin of the redox properties for these compounds. The optimised geometries of the cation radical, anion radical and dianion of compound 7 illustrate the structural changes induced by the charging process. For the dianion, the steric interactions are alleviated by rotation of the acceptor dicyanomethylene unit, but the presence of the donor dithiole group hinders the achievement of a fully aromatic planar structure for the central anthracene skeleton.
• BRYCE, MARTIN R.;MOORE, ADRIAN J.;LORCY, DOMINIQUE;DHINDSA, AJAIB S.;ROBE+, J. CHEM. SOC. CHEM. COMMUN.,(1990) N, C. 470-472
  作者：BRYCE, MARTIN R.、MOORE, ADRIAN J.、LORCY, DOMINIQUE、DHINDSA, AJAIB S.、ROBE+

  DOI：——

  日期：——