3-methylthio-2-naphthaldehyde | 364064-72-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-methylthio-2-naphthaldehyde
• 英文别名: 3-Methylsulfanylnaphthalene-2-carbaldehyde
• CAS: 364064-72-2
• 化学式: C₁₂H₁₀OS
• 分子量: 202.277
• InChiKey: LDDNRNSKVVDQCS-UHFFFAOYSA-N

物化性质

• 熔点：
  53.5-54.5 °C
• 沸点：
  359.9±25.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methylthio-2-naphthaldehyde 在 碘 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 31.0h， 生成 双萘并[2,3-B:2′,3′-F]噻吩并[3,2-B]噻吩
  参考文献：
  名称：

  Facile Synthesis of Highly π-Extended Heteroarenes, Dinaphtho[2,3-b:2‘,3‘-f]chalcogenopheno[3,2-b]chalcogenophenes, and Their Application to Field-Effect Transistors

  摘要：

  A facile three-step synthetic procedure for highly pi-extended heteroarenes, dinaphtho[2,3-b:2',3'-f]thieno[3,2-b]thiophene (DNTT) and dinaphtho[2,3-b:2',3'-f]selenopheno[3,2-b]selenophene (DNSS), was established. Solution UV-vis spectra and electrochemistry indicated that they have relatively low-lying HOMO levels and large HOMO-LUMO energy gaps. OFET devices fabricated with evaporated thin-films of DNTT and DNSS showed excellent FET characteristics in air, and the highest field-effect mobility of DNTT- and DNSS-based OFETs is 2.9 and 1.9 cm(2) V-1 s(-1), respectively.

  DOI：

  10.1021/ja068429z
• 作为产物：
  描述：

  3-(三氟甲基磺酰氧基)-2-萘甲酸甲酯 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 、 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.83h， 生成 3-methylthio-2-naphthaldehyde
  参考文献：
  名称：

  EP2740735

  摘要：

  公开号：

文献信息

• Rhodium(III)‐Catalyzed Aldehyde C−H Activation and Functionalization with Dioxazolones: An Entry to Imide Synthesis
  作者：Joe Massouh、Antoine Petrelli、Virginie Bellière‐Baca、Damien Hérault、Hervé Clavier

  DOI：10.1002/adsc.202101099

  日期：2022.2.15

  A rhodium(III)-based catalytic system has been used to develop a C−H bond activation of benzaldehyde derivatives and subsequent functionalization with dioxazolones in order to afford imides. The importance of the nature of the directing group to perform selectively the aldehydic C−H bond activation has been highlighted. The scope investigation showed that this transformation could be applied to various

  铑 (III) 基催化体系已被用于开发苯甲醛衍生物的 C-H 键活化和随后用二恶唑酮官能化以提供酰亚胺。已经强调了导向基团的性质对选择性地进行醛类 C-H 键活化的重要性。范围调查表明，这种转化可以应用于各种二恶唑酮和许多苯甲醛衍生物以及丙烯醛衍生物。酰亚胺产物的衍生反应证明了这种铑催化的醛 C-H 酰胺化的合成效用。
• Three Structural Isomers of Dinaphthothieno[3,2-<i>b</i>]thiophenes: Elucidation of Physicochemical Properties, Crystal Structures, and Field-Effect Transistor Characteristics
  作者：Tatsuya Yamamoto、Shoji Shinamura、Eigo Miyazaki、Kazuo Takimiya

  DOI：10.1246/bcsj.20090230

  日期：2010.2.15

  In order to gain an insight into the relationship between the molecular structure and the semiconductor characteristics of highly π-extended heteroarene-based organic semiconductors, three structural isomers of dinaphthothieno[3,2-b]thiophenes with C2h symmetry were investigated. Of these, two isomers, dinaphtho[2,1-b:2′,1′-f ]thieno[3,2-b]thiophene (2) and dinaphtho[1,2-b:1′,2′-f ]thieno[3,2-b]thiophene (3), were newly synthesized, characterized, and utilized as active semiconducting layers in organic field-effect transistors (FETs). Detailed investigation of the physicochemical properties of 2 and 3, together with another isomer, dinaphtho[2,3-b:2′,3′-f ]thieno[3,2-b]thiophene (1), indicated that the electronic structures of the three isomers are fairly different from each other despite having the same molecular formula and the same aromatic constituents. Comparison of the molecular arrangements in the crystals elucidated by X-ray structural analysis implied that the molecular shape and the thus-induced favorable intermolecular interactions play important roles in determining the entire molecular arrangement. The characteristics of 2- and 3-based FETs with maximum field-effect mobilities (μFET s) of 10−3–10−2 cm2 V−1 s−1 were inferior to those of 1-based FETs with μFET s up to 3.0 cm2 V−1 s−1. The inferior characteristics of 2- and 3-based devices were due to film morphology as elucidated by atomic force microscopy (AFM) and supported by theoretical calculations of electronic structure in the solid state. Together, the results indicate that the molecular structure and shape, even for similar heteroarenes with the same molecular formula and symmetry, are important parameters to determine the solid-state properties of organic semiconductors.

  为了深入了解高π延伸杂芳烃基有机半导体的分子结构与半导体特性之间的关系，研究了具有 C2h 对称性的二萘并[3,2-b]噻吩的三种结构异构体。其中，两种异构体，二萘并[2,1-b:2′,1′-f ]噻吩并[3,2-b]噻吩（2）和二萘并[1,2-b：1′,2′-f]噻吩[3,2-b]噻吩（3）进行了新的合成、表征，并将其用作有机场效应晶体管（FET）中的活性半导体层。对 2 和 3 以及另一种异构体二萘并[2,3-b:2′,3′-f ]噻吩并[3,2-b]噻吩（1）的理化性质进行的详细研究表明，尽管这三种异构体具有相同的分子式和相同的芳香成分，但它们之间的电子结构却有相当大的差异。通过 X 射线结构分析阐明的晶体中分子排列的比较表明，分子形状和由此引起的有利的分子间相互作用在决定整个分子排列中起着重要作用。2 基和 3 基场效应晶体管的最大场效应迁移率（μFET s）为 10-3-10-2 cm2 V-1 s-1，其特性不如 1 基场效应晶体管（μFET s 高达 3.0 cm2 V-1 s-1）。原子力显微镜（AFM）阐明了 2 基和 3 基器件的劣质特性与薄膜形态有关，固态电子结构的理论计算也支持了这一点。这些结果表明，即使是分子式和对称性相同的类似杂环戊烯，其分子结构和形状也是决定有机半导体固态特性的重要参数。
• NOVEL FUSED POLYCYCLIC AROMATIC COMPOUND, PROCESS FOR PRODUCING THE SAME, AND USE THEREOF
  申请人：Takimiya Kazuo

  公开号：US20100065826A1

  公开（公告）日：2010-03-18

  In one embodiment of the present invention, a novel fused polycyclic aromatic compound of the present invention is (a) a compound including a benzodichalcogenophenobenzodichalcogenophene (BXBX) skeleton further having an aromatic ring(s) located outside the BXBX skeleton, or (b) a compound including a BXBX skeleton in which a benzene ring is substituted with a heterocyclic ring. The compound can strengthen intermolecular interaction due to greater π electron orbits. This improves an electron field effect mobility of an organic semiconductor device that is manufactured by use of the compound as an organic semiconductor material. Further, since the number of fused rings included in the compound is small, the compound does not cause problems that generally occur in compounds having an extremely large number of fused rings, i.e., poor solubility in solvent and poor atmospheric stability due to high affinity to oxygen. As a result, the fused polycyclic aromatic compound of the present invention can be preferably used as an organic semiconductor material.

  在本发明的一种实施例中，本发明的新型融合多环芳香化合物是(a) 包括苯二卤素苯并二卤素苯并二卤素苯（BXBX）骨架，进一步具有位于BXBX骨架外部的芳香环，或者(b) 包括一个BXBX骨架，在其中苯环被杂环环取代的化合物。该化合物可以通过更大的π电子轨道强化分子间相互作用。这提高了由该化合物作为有机半导体材料制造的有机半导体器件的电子场效应迁移率。此外，由于化合物中包含的融合环数较少，因此该化合物不会引起通常出现在具有极大融合环数的化合物中的问题，即对溶剂的溶解度差和对氧气亲和力高导致的大气稳定性差。因此，本发明的融合多环芳香化合物可作为有机半导体材料优选使用。
• Method For Producing Aromatic Compound
  申请人：NIPPON KAYAKU KABUSHIKI KAISHA

  公开号：US20150239901A1

  公开（公告）日：2015-08-27

  A method for producing a heterocyclic compound represented by general formula (2) from a heterocyclic compound represented by general formula (1) (in the formulae, X1 represents a halogen atom; each of Y1 and Y2 independently represents an oxygen atom, sulfur atom, or selenium atom; each of R1 and R2 independently represents a substituent; m and n respectively represent the number of substituents R1 and R2, each of m and n representing an integer of 0-4; and when m and n are 2 or higher, R1 and R2 may be the same or different and may bond to each other to form an optionally substituted ring).

  一种从一般式（1）所表示的杂环化合物中制备一般式（2）所表示的杂环化合物的方法（在公式中，X1代表卤素原子；每个Y1和Y2分别表示氧原子、硫原子或硒原子；每个R1和R2分别表示取代基；m和n分别表示取代基R1和R2的数量，m和n分别表示0-4的整数；当m和n都为2或更高时，R1和R2可以相同或不同，并且可以连接以形成一个可选的取代环）。
• NOVEL ADDUCT COMPOUND, METHODS FOR PURIFICATION AND PREPARATION OF FUSED POLYCYCLIC AROMATIC COMPOUND, SOLUTION FOR FORMATION OF ORGANIC SEMICONDUCTOR FILM, AND NOVEL -DIKETONE COMPOUND
  申请人：Teijin Limited

  公开号：EP2471796A1

  公开（公告）日：2012-07-04

  Provided are a novel adduct compound and a novel α-diketone compound, from which organic semiconductor layers consisting of a fused polycyclic aromatic compound can be formed by a solution method, said solution method being generally easier than a deposition method. Also provided are a method for the purification of the adduct compound, and a solution for the formation of organic semiconductor film, which contains the adduct compound. The adduct compound has a structure wherein a compound having a double bond is added in an eliminable state to a fused polycyclic aromatic compound of general formula (I): Ar1Ar2Ar3 (I), while the α-diketone compound has a structure wherein a compound having a double bond is added in an eliminable state to a fused polycyclic aromatic compound. The fused polycyclic aromatic compound is dinaphthothienothiophene or the like, while the compound having a double bond is hexachlorocyclopentadiene or the like. In general formula (I), Ar1, Ar2 and Ar3 are each as defined in the description.

  本发明提供了一种新型加成化合物和一种新型α-二酮化合物，通过溶液法可以形成由融合多环芳香族化合物组成的有机半导体层，所述溶液法通常比沉积法更容易。此外，还提供了一种纯化加合物的方法，以及一种用于形成有机半导体薄膜的溶液，其中含有加合物。该加成化合物具有如下结构：在通式（I）的融合多环芳香族化合物中以消去状态加入具有双键的化合物：Ar1Ar2Ar3(I)，而 α-二酮化合物的结构是具有双键的化合物以消去状态加入到融合多环芳香族化合物中。融合的多环芳烃化合物是二萘并噻吩或类似物，而具有双键的化合物是六氯环戊二烯或类似物。在通式（I）中，Ar1、Ar2 和 Ar3 分别如描述中所定义。