BBTBDT | 1000973-63-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: BBTBDT
• 英文别名: bis[1]benzothieno[2,3-d;2',3'-d']benzo[1,2-b;4,5-b']dithiophene；bis[1]benzothieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene；5,13,18,26-Tetrathiaheptacyclo[14.10.0.03,14.04,12.06,11.017,25.019,24]hexacosa-1(16),2,4(12),6,8,10,14,17(25),19,21,23-undecaene
• CAS: 1000973-63-6
• 化学式: C₂₂H₁₀S₄
• 分子量: 402.585
• InChiKey: IWMVCGAMAGCYDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-乙炔基-2-(甲硫基)苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 碘苯二乙酸 、 碘 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 BBTBDT
  参考文献：
  名称：

  通过炔烃的连续碘化/光环化合成[1] Benzothieno [3,2- b ] [1]苯并噻吩衍生物

  摘要：

  开发了一种新的[1]苯并噻吩并[3,2- b ] [1]苯并噻吩衍生物（BTBTs）的合成方法。本方法包括1，2-双（2-甲基硫代苯基）乙炔的碘环化和3-碘-（2-甲基硫代苯基）苯并[ b ]噻吩的光解。在室温下，在CH 2 Cl 2中用I 2 / PhI（OAc）2处理1,2-双（2-甲基硫代苯基）乙炔，在硫上进行选择性环化，得到3-碘-（2-甲基硫代苯基）苯并[ b ]噻吩，收率高。碘化苯并[ b]的辐照高压汞灯（> 290 nm）产生的]噻吩可提供高收率的BTBT。此外，本方法应用于双[1]苯并噻吩并[2,3- d ; 2'，3'- d ']苯并[1,2- b ; 4,5- b ']二噻吩的合成（BBTBDT ）。

  DOI：

  10.1021/acs.joc.9b00213

文献信息

• Consecutive Thiophene-Annulation Approach to π-Extended Thienoacene-Based Organic Semiconductors with [1]Benzothieno[3,2-<i>b</i>][1]benzothiophene (BTBT) Substructure
  作者：Takamichi Mori、Takeshi Nishimura、Tatsuya Yamamoto、Iori Doi、Eigo Miyazaki、Itaru Osaka、Kazuo Takimiya

  DOI：10.1021/ja406257u

  日期：2013.9.18

  to the [1]benzothieno[3,2-b][1]benzothiophene (BTBT) substructure featuring two consecutive thiophene-annulation reactions from o-ethynyl-thioanisole substrates and arylsulfenyl chloride reagents that can be easily derived from arylthiols. The method is particularly suitable for the synthesis of unsymmetrical derivatives, e.g., [1]benzothieno[3,2-b]naphtho[2,3-b]thiophene, [1]benzothieno[3,2-b]anthra[2

  我们描述了 [1] 苯并噻吩并 [3,2-b][1] 苯并噻吩 (BTBT) 亚结构的新合成路线，该亚结构具有来自邻乙炔基-苯硫醚底物和芳基亚磺酰氯试剂的两个连续噻吩环化反应，这些反应很容易衍生来自芳硫醇。该方法特别适用于不对称衍生物的合成，例如[1]苯并噻吩并[3,2-b]萘并[2,3-b]噻吩、[1]苯并噻吩并[3,2-b]蒽[2] 3-b]噻吩和萘并[3,2-b]噻吩并[3,2-b]蒽[2,3-b]噻吩，一种含硒衍生物，[1]苯并噻吩并[3,2-b] [1]苯并硒酚。它还允许我们访问具有两个 BTBT 子结构的 π 扩展衍生物，例如，双 [1] 苯并噻吩并 [2,3-d:2',3'-d']benzo[1,2-b:4,5 -b']二噻吩和双[1]苯并噻吩[2,3-d:2',3'-d']萘并[2,3-b:6,7-b']二噻吩(BBTNDT)。应该强调的是，这些新的BTBT衍生物很难合成。
• Synthesis of [1]benzothieno[3,2-b][1]benzothiophene (BTBT) and its higher homologs through palladium-catalyzed intramolecular decarboxylative arylation
  作者：Sojiro Minami、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1016/j.tetlet.2014.05.084

  日期：2014.7

  We report herein an effective method for the construction of 4- and 7-ring benzo-fused thieno[3,2-b]thiophenes, involving palladium-catalyzed intramolecular decarboxylative arylation as the key step.

  我们在此报告了构建4和7环苯并稠合的噻吩并[3,2- b ]噻吩的有效方法，其中涉及钯催化的分子内脱羧芳基化。
• [EN] HIGH PERFORMANCE SOLUTION PROCESSABLE SEMINCONDUCTOR BASED ON DITHIENO [2,3-D:2',3'-D']BENZO[1,2-B:4,5-B'] DITHIOPHENE<br/>[FR] SEMI-CONDUCTEUR À HAUTE PERFORMANCE APTE À ÊTRE TRAITÉ EN SOLUTION À BASE DE DITHIÉNO[2,3-D:2',3'-D']BENZO[1,2-B:4,5-B']DITHIOPHÈNE
  申请人：BASF SE

  公开号：WO2010000670A1

  公开（公告）日：2010-01-07

  Dithienobenzodithiophenes of general formula (I) in which R1 to R6 are each independently selected from a) H, b) halogen, c) -CN, d) -NO2, e) - OH, f) a C1-20 alkyl group, g) a C2-20 alkenyl group, h) a C2-20 alkynyl group, i) a C1-20 alkoxy group, j) a C1-20 alkylthio group, k) a C1-20 haloalkyl group, I) a -Y- C3-10 cycloalkyl group, m) a -Y-C6-14 aryl group, n) a -Y-3-12 membered cyclo- heteroalkyl group, or o) a -Y-5-14 membered heteroaryl group, wherein each of the C1-20 alkyl group, the C2-20 alkenyl group, the C2-20 alkynyl group, the C3-10 cycloalkyl group, the C6-14 aryl group, the 3-12 membered cyc- loheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1 -4 R7 groups, wherein R1 and R3 and R2 and R4 may also together form an aliphatic cyclic moiety, Y is independently selected from divalent a C1-6 alkyl group, a divalent C1-6 haloalkyl group, or a covalent bond; and m is independently selected from 0, 1, or 2. The invention also relates to the use of the dithienobenzodithiophenes according to any of claims 1 to 4 as semiconductors or charge transport materials, as thin-film transistors (TFTs), or in semiconductor components for organic light-emitting diodes (OLEDs), for photovoltaic components or in sensors, as an electrode material in batteries, as optical waveguides or for electrophotography applications.

  通式（I）的二噻吩并二噻吩（dithienobenzodithiophenes），其中R1至R6分别独立地选自a）H，b）卤素，c）-CN，d）-NO2，e）-OH，f）C1-20烷基，g）C2-20烯基，h）C2-20炔基，i）C1-20烷氧基，j）C1-20烷硫基，k）C1-20卤代烷基，I）-Y-C3-10环烷基，m）-Y-C6-14芳基，n）-Y-3-12成员环杂烷基，或o）-Y-5-14成员杂芳基，其中C1-20烷基，C2-20烯基，C2-20炔基，C3-10环烷基，C6-14芳基，3-12成员环杂烷基和5-14成员杂芳基中的每一个均可选择性地用1-4个R7基取代，其中R1和R3以及R2和R4也可以共同形成脂肪族环状基团，Y独立地选自二价的C1-6烷基，二价的C1-6卤代烷基或共价键；m独立地选自0、1或2。本发明还涉及将通式1至4中的二噻吩并二噻吩用作半导体或电荷传输材料，用作薄膜晶体管（TFT），或用于有机发光二极管（OLED）的半导体元件，用于光伏元件或传感器，用作电池的电极材料，用作光波导或电子摄影应用。
• Organic Single-Crystal Transistors Based on π-Extended Heteroheptacene Microribbons
  作者：Yu Seok Yang、Takuma Yasuda、Chihaya Adachi

  DOI：10.1246/bcsj.20120178

  日期：2012.11.15

  Facile synthesis of a new series of π-extended thienoacenes has been described. Their electronic structures have been elucidated by UV–vis absorption and photoelectron spectra. Well-defined single-crystal microribbons composed of self-organized thienoacene molecules have been fabricated using physical vapor transport, and have been applied to field-effect transistors. The organic transistors employing the single-crystal microribbons exhibit mobilities as high as 0.47 cm2 V s−1 with on/off ratios of ca. 106.

  已描述了新系列π-扩展噻吩并苯并吡喃的简易合成。通过紫外-可见光吸收和光电子能谱阐明了它们的电子结构。使用物理汽相传输法制造了由自组织噻吩并苯并吡喃分子组成的定义明确的单晶微带，并将其应用于场效应晶体管。采用单晶微带的有机晶体管表现出高达0.47 cm2 V s−1的迁移率，开/关比约为106。
• HETEROACENE DERIVATIVE, TETRAHALOTERPHENYL DERIVATIVE, AND PROCESSES FOR PRODUCING THE SAME
  申请人：Watanabe Makoto

  公开号：US20090261300A1

  公开（公告）日：2009-10-22

  There are provided a heteroacene derivative having an excellent oxidation resistance and capable of forming a semiconductor active phase by a coating process, and an oxidation-resistant organic semiconductor material using the same, as well as an organic thin film. [Means for Resolution] A heteroacene derivative represented by the formula (1) is obtained by tetrametalation of a tetrahaloterphenyl derivative with a metalation agent and subsequent treatment of the resulting compound with reaction agents: wherein the substituents R 1 to R 4 are the same or different and each represents a hydrogen atom, a fluorine atom, a chlorine atom, an aryl group having 4 to 30 carbon atoms, an alkyl group having 3 to 20 carbon atoms, or a halogenated alkyl group having 1 to 20 carbon atoms; T 1 and T 2 are the same or different and each represents sulfur, selenium, tellurium, oxygen, phosphorus, boron, or aluminum; l and m each is an integer of 0 or 1; and rings A and B are the same or different and each has a structure represented by the following formulae (A- 1 ) or (A-2).

  提供了一种具有优异氧化抗性并能够通过涂层工艺形成半导体活性相的杂环芳烃衍生物以及使用该衍生物的抗氧化有机半导体材料，以及有机薄膜。[解决方案] 通过使用金属化试剂四甲基化四卤代苯衍生物并随后用反应试剂处理所得化合物，获得了由式（1）表示的杂环芳烃衍生物：其中取代基R1至R4相同或不同，每个代表氢原子、氟原子、氯原子、具有4至30个碳原子的芳基、具有3至20个碳原子的烷基或具有1至20个碳原子的卤代烷基；T1和T2相同或不同，每个代表硫、硒、碲、氧、磷、硼或铝；l和m各自为0或1的整数；环A和环B相同或不同，每个具有以下式（A-1）或（A-2）所表示的结构。