4-naphthyl-1,3-dithio-2-one | 1236364-77-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-naphthyl-1,3-dithio-2-one
• 英文别名: 4-naphthyl-1,3-dithiol-2-one；4-(2-naphthyl)[1,3]dithiol-2-one；2-naphthyl-[1,3]dithiol-2-one；naphthyl-[1,3]dithiol-2-one；4-Naphthalen-2-yl-1,3-dithiol-2-one
• CAS: 1236364-77-4
• 化学式: C₁₃H₈OS₂
• 分子量: 244.338
• InChiKey: QSWLKGRHTVJPNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• 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：

  4-naphthyl-1,3-dithio-2-one 在 乙醇 、 碘 、 potassium hydroxide 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Photoconducting Devices with Response in the Visible–Near-Infrared Region Based on Neutral Ni Complexes of Aryl-1,2-dithiolene Ligands

  摘要：

  属于[Ni(Ar-edt)2]x- [Ar-edt2- = 芳基乙烯-1,2-二硫酸盐；Ar = 苯基、（1x-）、2-萘基（2x-）；x = 0 和 1]通过核磁共振、紫外-可见-近红外（UV-vis-NIR）、漫反射和傅立叶变换红外光谱以及循环伏安法和单晶 X 射线衍射分析进行了全面表征。这些复合物已成为新的光导材料，可用于开发在可见光-近红外区域有响应的光检测器原型。在某些情况下，这些光电检测装置的量子效率要比之前报道的 1,2-二硫环戊烯系统高出几个数量级。

  DOI：

  10.1021/acs.inorgchem.0c00491
• 作为产物：
  描述：

  2-萘乙酮 在 高氯酸 、 溴 作用下， 以 氯仿 、 丙酮 为溶剂， 生成 4-naphthyl-1,3-dithio-2-one
  参考文献：
  名称：

  Molybdenum(vi) tris(dithiolene) complexes as a new class of three-dimensional two-photon absorption chromophores at telecommunications wavelengths

  摘要：

  研究人员合成了两种具有苯基或萘基取代基的三(二硫环戊烯)钼(VI)配合物，并利用近红外飞秒激光脉冲，通过开孔 Z 扫描技术研究了它们的双光子吸收特性。这两种复合物都在 1.3 μm 波长附近表现出显著的双光子截面，其中萘基取代的复合物表现出 660 × 10-50 cm4 s-1 光子-1 的双光子截面，这表明有一类新的三维发色团可用于电信波长。

  DOI：

  10.1039/c3tc31058b

文献信息

• Selective Capture of Ni ²⁺ Ions by Naphthalene‐ and Coumarin‐Substituted Dithiolenes
  作者：Ashta C. Ghosh、Klaus Weisz、Carola Schulzke

  DOI：10.1002/ejic.201500847

  日期：2016.1

  Naphthalene- and coumarin-substituted dithiolene ligands were synthesized, and their coordination behavior towards different metal ions, including biologically relevant ions like Cu+, Cu2+, and Fe3+, was tested. Both ligands bind nickel selectively and show no evidence of binding any other metal investigated. Particularly, the compound bearing the fluorophore coumarin can serve as a colorimetric (“naked

  合成了萘和香豆素取代的二硫烯配体，并测试了它们对不同金属离子的配位行为，包括生物相关离子，如 Cu+、Cu2+ 和 Fe3+。两种配体都选择性地结合镍，并且没有显示出结合任何其他研究的金属的证据。特别是，带有荧光团香豆素的化合物可用作比色（“裸眼”）和开关荧光标记，用于检测具有特征近红外 (NIR) 特征的 Ni2+ 离子，即使存在各种过渡金属离子，通常很难与镍区分开来。竞争性荧光实验表明，伴随存在的 Ag+、Al3+、Ca2+、Cd2+、Co2+、Cu+、Cu2+、Fe3+、Hg2+、Mg2+、Mn2+、Pb2+、Sn2+、Zn2+、和 MoO42– 不能抑制或减弱 Ni2+ 特异性荧光猝灭，强调了系统固有的 Ni2+ 离子选择性。通过在THF/MeOH溶液中的荧光滴定实验详细研究了标记物与Ni2+的配位行为。确定 X 射线结构以补充前体和萘-二硫烯-镍配合物的表征。
• Synthesis and Characterization of Novel Gold(III) Complexes of Asymmetrically Aryl-Substituted 1,2-Dithiolene Ligands Featuring Potential-Controlled Spectroscopic Properties
  作者：Lucia Ambrosio、M. Carla Aragoni、Massimiliano Arca、Francesco A. Devillanova、Michael B. Hursthouse、Susanne L. Huth、Francesco Isaia、Vito Lippolis、Annalisa Mancini、Anna Pintus

  DOI：10.1002/asia.200900690

  日期：2010.4.23

  unsymmetrically substituted Ar,H‐edt2− 1,2‐dithiolene ligands (Ar,H‐edt2−=arylethylene‐1,2‐dithiolato; Ar=phenyl (1−), 2‐naphthyl (2−), and 1‐pyrenyl (3−)) were synthesized and characterized by spectroscopic and electrochemical methods and the corresponding neutral species (1, 2, and 3, respectively) were obtained in CH2Cl2 solution at room temperature by diiodine oxidation. The single‐crystal X‐ray

  四丁基（TBA +）的不对称取代的Ar，H-EDT的正方形平面单阴离子金络合物的盐2- 1,2-二硫配体（氩气，H-EDT -2- = arylethylene -1,2- dithiolato; Ar为苯基（1 - ），2-萘基（2 - ），和1-芘基（3 - ））的合成和表征通过光谱和电化学方法和相应的中性物质（1，2，和3分别）在获得CH 2 Cl 2溶液在室温下经二碘氧化。收集（TBA单晶X射线衍射结构数据+）（2 - ），通过DFT理论计算的支持，是与配位体和Au的烯-1,2-二硫醇形式一致III氧化态。所有配合物在中性状态下均具有强烈的近红外吸收（约1.5μm），并且在400–550 nm范围内具有可见光发射特性，在3 −情况下，其能量由配合物的电荷控制/ 3对。光谱和电化学特征1 X -和2 X - （X= 0，1），通过DFT和时间依赖性（TD）DFT计算研究了顺式和反式构型。
• Synthesis, characterization and oxygen atom transfer reactivity of a pair of Mo(<scp>iv</scp>)O- and Mo(<scp>vi</scp>)O₂-enedithiolate complexes – a look at both ends of the catalytic transformation
  作者：Ashta C. Ghosh、Prinson P. Samuel、Carola Schulzke

  DOI：10.1039/c7dt01470h

  日期：——

  new molybdenum complexes (Bu4N)2[MoIVO(ntdt)2] (1) and (Ph4P)2[MoVIO2(ntdt)2] (2) (ntdt = 2-naphthyl-1,4-dithiolate) were synthesized using asymmetric dithiolene precursors and were characterized as structural models for the active site of arsenite oxidase, a molybdopterin bearing enzyme. The ligand was obtained readily by a two-step synthesis starting from 2-bromo-2′-acetonapthone. Complexes 1 and

  两个新的钼配合物（Bu 4 N）2 [Mo IV O（ntdt）2 ]（1）和（Ph 4 P）2 [Mo VI O 2（ntdt）2 ]（2）（ntdt = 2-萘基-1 （4-二硫代），是使用不对称的二硫代烯前体合成的，并被表征为亚砷酸氧化酶（一种含钼蝶呤的酶）的活性位点的结构模型。从2-溴-2'-丙酮ap开始，通过两步合成容易获得配体。通过使所得的4-萘基-1,3-二硫醇-2-酮与金属前体反应获得配合物1和2。反式- [的MoO 2（CN）4 ] 4-和顺- [的MoO 2（NCS）4 ] 2-分别。值得注意的是，据我们所知，这项工作构成了后者在二硫代烯化学中的首次应用。通过NMR和IR光谱，通过循环伏安法，质谱，元素分析以及在1的情况下通过单晶X射线衍射来表征图1和图2。化合物1的分子结构表现出较少见的顺式异构体形式（即2-萘基1,4-二硫代磺酸盐配体的萘基位于MoS的同一侧4方形底
• Platinum diimine-dithiolate complexes as a new class of photoconducting compounds for pristine photodetectors: case study on [Pt(bipy)(Naph-edt)] (bipy = 2,2′-bipyridine; Naph-edt²⁻ = 2-naphthylethylene-1,2-dithiolate)
  作者：M. Carla Aragoni、Massimiliano Arca、Maddalena Binda、Claudia Caltagirone、Vito Lippolis、Dario Natali、Enrico Podda、Marco Sampietro、Anna Pintus

  DOI：10.1039/d1dt01288f

  日期：——

  The photoconducting properties of platinum diimine-dithiolate complex [Pt(bipy)(Naph-edt)] (1; bipy = 2,2′-bipyridine; Naph-edt2− = 2-naphthylethylene-1,2-dithiolate) were investigated. DFT calculations on a model assembly with four complex units suggest that the high external quantum efficency measured on a prototype photodetector correlates with the intermolecular character of electronic excitations

  研究了铂二亚胺-二硫醇盐络合物[Pt（bipy）（Naph-edt）]（1 ; bipy = 2,2'-bipyridine; Naph-edt 2- = 2-萘基乙烯-1,2-二硫醇盐）的光电导性能。在具有四个复杂单元的模型组件上的DFT计算表明，在原型光电探测器上测得的高外部量子效率与可见光区域中电子激发的分子间特性相关。
• Structure–Property Relationships in Pt ^II Diimine‐Dithiolate Nonlinear Optical Chromophores Based on Arylethylene‐1,2‐dithiolate and 2‐Thioxothiazoline‐4,5‐dithiolate
  作者：Anna Pintus、M. Carla Aragoni、Nathalie Bellec、Francesco A. Devillanova、Dominique Lorcy、Francesco Isaia、Vito Lippolis、Rebecca A. M. Randall、Thierry Roisnel、Alexandra M. Z. Slawin、J. Derek Woollins、Massimiliano Arca

  DOI：10.1002/ejic.201200346

  日期：2012.8

  AbstractEighteen new [PtII(N∧N)(S∧S)] complexes [23–40; N∧N = diimine: 2,2′‐bipyridine, 1,10‐phenanthroline and alkyl/aryl‐substituted derivatives; S∧S = arylethylene‐1,2‐dithiolate (R‐edt2–: R = phenyl, 2‐naphthyl, 1‐pyrenyl), N‐substituted 2‐thioxothiazoline‐4,5‐dithiolate (R‐dmet2–: R = methyl, ethyl, phenyl)] have been synthesized and characterized by spectroscopic (UV/Vis/NIR, fluorescence) and electrochemical (CV) measurements. Single‐crystal X‐ray diffraction analysis allowed structural characterization of five of the complexes (27–29, 31, and 37). Structural modifications capable of affecting the nature and energies of the frontier molecular orbitals in these systems were assessed and hybrid DFT and time‐dependent (TD) DFT calculations, carried out both in the gas phase and in the presence of several solvents (CH2Cl2, CHCl3, CH3CN, acetone, thf, dmf, dmso, and toluene), allowed the trends observed in the voltammetric data and in the energies of the peculiar solvatochromic visible absorption bands to be rationalized. In addition, to evaluate the second‐order nonlinear optical properties of 23–40, first static hyperpolarizability values βtot were calculated both in the gas phase and in CH2Cl2, the highest values being obtained for [Pt(N∧N)(Me‐dmet)] complexes (N∧N = 4,4′‐diphenyl‐2,2′‐bipyridine and 4,7‐diphenyl‐1,10‐phenanthroline; βtot = 691 × 10–30 and 604 × 10–30 esu, respectively).