1,6-dithiapyrene | 194-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫色烯
• 英文名称: 1,6-dithiapyrene
• 英文别名: thiochromeno[6,5,4-def]thiochromene；Thiochromeno[6,5,4-def]thiochromen；Naphtho<1.8-bc;5.4-b'c'>dithiopyran；5,12-dithiatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),6,8,10,13-heptaene
• CAS: 194-07-0
• 化学式: C₁₄H₈S₂
• 分子量: 240.35
• InChiKey: QSYGNDJNQJUBTE-UHFFFAOYSA-N

物化性质

• 熔点：
  224-225 °C
• 沸点：
  447.1±45.0 °C(Predicted)
• 密度：
  1.436±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 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：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,6-dithiapyrene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 complex of 2,7-bis(methylthio)-1,6-dithiapyrene and p-chloranil
  参考文献：
  名称：

  甲硫基和乙二基二硫基取代的 1,6-二硫杂芘及其电荷转移配合物：新的有机分子金属

  摘要：

  2,7-双(甲硫基)-1,6-二硫杂芘(MTDTPY)和2,3:7,8-双(乙二硫基)-1,6-二硫杂芘(ETDTPY)的合成和物理性质及其电荷转移报道了复合物。MTDTPY 由 1,6-二硫杂芘制备。ETDTPY 由萘-1,5-二硫醇分四步制备。这两个新供体显示出可逆的两阶段氧化还原行为，其电位与四硫富瓦烯相当。MTDTPY 产生了 1:1 TCNQ 复合物的两个结晶相，..cap α..-形式（单斜，P2/sub 1//c）和 ..beta..-形式（三斜，P anti 1），分别由供体和受体的混合堆叠和均匀隔离堆叠组成。..beta..-形式包含相邻供体柱之间的短 S...S 接触（3.48 和 3.57 A）。..beta.. 的单晶电导率 -形式是金属的（sigma/sub rt/ = 110 S cm/sup -1/，T/sub c/ = 110 K），而..cap alpha

  DOI：

  10.1021/ja00257a011
• 作为产物：
  描述：

  1,5-bis-(2,2-dimethoxy-ethylsulfanyl)-naphthalene 在 磷酸 、 phosphorus pentoxide 作用下， 生成 1,6-dithiapyrene
  参考文献：
  名称：

  Tilak, Proceedings - Indian Academy of Sciences, Section A, 1951, # 33, p. 71,75

  摘要：

  DOI：

文献信息

• Organic Semiconductors and Their Manufacture
  申请人：Berens Ulrich

  公开号：US20090299070A1

  公开（公告）日：2009-12-03

  The invention relates to a semiconductor device comprising a compound of the formula I and of the formula XXI, wherein the symbols have the meanings defined in the specification, to the novel compounds of the formula I and XXI and to the use of such a compound as an organic semiconductor for the preparation of an electronic device, and further compounds and devices, as well as other embodiments given in the specification.

  本发明涉及一种半导体器件，包括式I和式XXI的化合物，其中符号的含义在规范中定义，以及式I和XXI的新化合物以及将此类化合物用作有机半导体以制备电子器件，以及规范中给出的其他化合物和器件等其他实施例。
• Contrasting Photodynamics between C₆₀-Dithiapyrene and C₆₀-Pyrene Dyads
  作者：Dirk M. Guldi、Fabian Spänig、David Kreher、Igor F. Perepichka、Cornelia van der Pol、Martin R. Bryce、Kei Ohkubo、Shunichi Fukuzumi

  DOI：10.1002/chem.200700837

  日期：2008.1

  The photodynamics of a C60-dithiapyrene donor-acceptor conjugate were compared with the corresponding C60-pyrene conjugate. The photoinduced charge separation and subsequent charge recombination processes were examined by time-resolved fluorescence measurements on the picosecond timescale and transient absorption measurements on the picosecond and microsecond timescales with detection in the visible

  将C60-二硫杂donor供体-受体缀合物的光动力学与相应的C60-py杂合物进行了比较。通过在皮秒时间尺度上的时间分辨荧光测量以及在皮秒和微秒时间尺度上的瞬态吸收测量以及在可见光和近红外区域中的检测，检查了光诱导的电荷分离和随后的电荷重组过程。我们已经观察到在C60-二硫杂py二聚体中光生电荷分离状态的寿命很长（即高达1.01 ns），而无需i）两个部分之间的间隔长，或ii）芳族化合物芳香性的增加。自由基离子对。
• Quinoid Systems as Organic Semiconductors
  申请人：Berens Ulrich

  公开号：US20090261321A1

  公开（公告）日：2009-10-22

  A semiconducting layer comprising a non-polymeric quinoid heteroacene compound of the formula (I) wherein X stands for O, S or NR, each of R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 being independently selected from hydrogen and an organic residue, or 2 or more thereof together forming one or more annealed rings, which may be substituted or unsubstituted, carbocyclic or helerocyclic, aromatic, quinoid or aliphatic, may be used e.g. for the manufacture of a diode, an organic field effect transistor, an organic thin film transistor, or a device containing a diode and/or an organic field effect transistor and/or organic thin film transistor.

  一种半导体层，包括式(I)的非聚合物醌类杂芳烃化合物，其中X代表O，S或NR，R，R1，R2，R3，R4，R5，R6，R7，R8中的每一个都是独立选择的氢原子或有机残基，或者其中2个或2个以上在一起形成一个或多个退火环，这些环可以是取代或未取代的，碳环或杂环，芳香性，醌类或脂肪族的，例如可用于制造二极管、有机场效应晶体管、有机薄膜晶体管或包含二极管和/或有机场效应晶体管和/或有机薄膜晶体管的器件。
• First Syntheses of Iodinated 1,6-Dithiapyrene Derivatives
  作者：Yasushi Morita、Eigo Miyazaki、Jiro Toyoda、Kazuhiro Nakasuji

  DOI：10.1246/bcsj.76.205

  日期：2003.1

  An improved synthetic method of 1,6-dithiapyrene (DTPY) was found with a practical yield in a reproducible manner. Iodinated DTPY derivatives were prepared as new donor molecules, and the crystal structure of 2,7-diiodoDTPY was clarified by an X-ray structure analysis.

  发现了一种改进的 1,6-二硫杂芘 (DTPY) 合成方法，以可重现的方式获得了实用的产率。制备了碘化 DTPY 衍生物作为新的供体分子，并通过 X 射线结构分析阐明了 2,7-二碘 DTPY 的晶体结构。
• Crystal and Electronic Structures of Radical Salts of 2,7-Bis(methylthio)-1,6-dithiapyrene (MTDTPY) and 2,7-Bis(methylseleno)-1,6-dithiapyrene (MSDTPY)
  作者：Atsushi Kawamoto、Jiro Tanaka、Akio Oda、Hideshi Mizumura、Ichiro Murata、Kazuhiro Nakasuji

  DOI：10.1246/bcsj.63.2137

  日期：1990.8

  Radical salts of 2,7-bis(methylthio)-1,6-dithiapyrene (MTDTPY) with PF6− and 2,7-bis(methylseleno)-1,6-dithiapyrene (MSDTPY) with AsF6− and [Au(CN)2]− were prepared using an electrochemical method. The crystal structures of these salts were determined with an X-ray method. MTDTPY–(PF6)0.67 (triclinic P\bar1) and MSDTPY–(AsF6)0.67 (triclinic P\bar1) form uniform segregated stacks of MTDTPY and MSDTPY molecules with interplanar distances of 3.40 and 3.59 Å, respectively. Short S–S contacts of 3.46–3.56 Å for MTDTPY–(PF6)0.67 and 3.54–3.61 Å for MSDTPY–(AsF6)0.67 were observed between the columns. The chains of disordered PF6− and AsF6− were found to be parallel to the stack axis. Analysis of the disorder showed a stoichiometric ratio of the DTPY derivatives and counter anions at 1:0.67; the formal charge of MTDTPY and MSDTPY was estimated at +0.67. MSDTPY–Au(CN)2 (monoclinic P2/c) forms a segregated stack of MSDTPY molecules with an interplanar distance of 3.40 Å. The optical reflection spectra of these crystals were measured with polarized light both parallel and perpendicular to the stack axis. In spite of the short intercolumnar S–S contacts, the spectra of MTDTPY–(PF6)0.67 and MSDTPY–(AsF6)0.67 showed a strong one-dimensional character. The optical conductivity spectra (σ(ω)) and the real part of the dielectric constant (ε′(ω)) along the stack axis were obtained by means of Kramers–Kronig transformation. Both the conductivity spectra and the dielectric constant substantially differ from the simple Drude model. These results were analyzed with a one-dimensional electron-localization model in a disordered system with the following optical parameters: ωp=14000 cm−1; τi=2.2×10−15s (τi−1=2400 cm−1) and εcore=3.0 for MTDTPY-(PF6)0.67 and ωp=10000 cm−1; τi=2.2×10−15 (τi−1=2400 cm−1) and εcore=3.5 for MSDTPY–(AsF6)0.67. From the spectra of MSDTPY–Au(CN)2, the on-site Coulomb repulsion U was estimated at 6000 cm−1.

  采用电化学方法制备了 2,7-双（甲硫基）-1,6-二硫杂蒽 (MTDTPY) 与 PF6- 和 2,7-双（甲基硒基）-1,6-二硫杂蒽 (MSDTPY) 与 AsF6- 和 [Au(CN)2]- 的自由基盐。用 X 射线法测定了这些盐的晶体结构。MTDTPY-(PF6)0.67 (triclinic P\bar1) 和 MSDTPY-(AsF6)0.67 (triclinic P\bar1) 形成了均匀的 MTDTPY 和 MSDTPY 分子分离堆积，平面间距分别为 3.40 和 3.59 Å。柱体之间的短 S-S 接触（MTDTPY-(PF6)0.67 为 3.46-3.56 Å，MSDTPY-(AsF6)0.67 为 3.54-3.61 Å）。无序的 PF6- 和 AsF6- 链平行于堆积轴。无序分析表明，DTPY 衍生物和反阴离子的化学计量比为 1:0.67；MTDTPY 和 MSDTPY 的形式电荷估计为 +0.67。MSDTPY-Au(CN)2（单斜 P2/c）形成了 MSDTPY 分子的分离堆积，其平面间距为 3.40 Å。尽管柱间 S-S 接触很短，但 MTDTPY-(PF6)0.67 和 MSDTPY-(AsF6)0.67 的光谱显示出很强的一维特征。通过克雷默-克罗尼格变换，获得了沿堆叠轴的光导光谱（σ(ω)）和介电常数的实部（ε′(ω)）。导电光谱和介电常数都与简单的德鲁德模型有很大不同。这些结果是通过无序体系中的一维电子定位模型进行分析的，光学参数如下：ωp=14000 cm-1; τi=2.2×10-15s（τi-1=2400 cm-1），εcore=3.0（MTDTPY-(PF6)0.67），ωp=10000 cm-1；τi=2.2×10-15（τi-1=2400 cm-1），εcore=3.5（MSDTPY-(AsF6)0.67）。根据 MSDTPY-Au(CN)2 的光谱，现场库仑斥力 U 被估计为 6000 cm-1。