4,7-bis(5'-hexyl-2,2'-bithienyl-5-yl)-2,1,3-benzothiadiazole | 1027318-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 4,7-bis(5'-hexyl-2,2'-bithienyl-5-yl)-2,1,3-benzothiadiazole
• 英文别名: 4,7-Bis[5-(5-hexylthiophen-2-yl)thiophen-2-yl]-2,1,3-benzothiadiazole；4,7-bis[5-(5-hexylthiophen-2-yl)thiophen-2-yl]-2,1,3-benzothiadiazole
• CAS: 1027318-35-9
• 化学式: C₃₄H₃₆N₂S₅
• 分子量: 633.003
• InChiKey: PZKWTFPAZLTXIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  167
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4,7-二(噻吩-2-基)苯并[c][1,2,5]噻二唑 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 4,7-bis(5'-hexyl-2,2'-bithienyl-5-yl)-2,1,3-benzothiadiazole
  参考文献：
  名称：

  噻吩/呋喃取代对芳基噻二唑基有机半导体有机场效应晶体管性能的影响

  摘要：

  对于有机场效应晶体管（OFET）应用，研究了四种供体-受体（D-A）型有机半导体，它们由5-己基噻吩与噻吩/呋喃侧苯并噻二唑/萘噻二唑组成。尽管呋喃是噻吩的类似物，但由于其与噻吩的性质不同以及光化学氧化的不稳定性，它在有机电子领域的关注较少。但是，这项研究确定呋喃可以显示与其类似物相当的电荷传输性质。研究了带有苯并基和不同杂原子侧翼基团的电子接受噻二唑核的扩展，表明OFET的性能取决于分子轨道，几何形状和堆积。底栅底接触装置的配置用于研究所有分子的OFET传输性质。我们成功地证明了呋喃单元是一种有希望的流动性构建基块（μ最大）的0.0122厘米2 V -1小号-1用于使用设备呋喃基取代的苯并噻二唑作为沟道层。

  DOI：

  10.1039/d0tc04982d

文献信息

• PROCESS FOR THE PREPARATION OF BENZOHETERO [1,3] - DIAZOLE COMPOUNDS DISUBSTITUTED WITH HETEOARYL GROUPS
  申请人：Schimperna Giuliana

  公开号：US20140221663A1

  公开（公告）日：2014-08-07

  Process for the preparation of a benzohetero[1,3]diazole compound disubstituted with heteroaryl groups which comprises reacting at least one benzohetero[1,3]diazole compound disubstituted with at least one heteroaryl compound. Said benzohetero[1,3]diazole compound disubstituted with heteroaryl groups can be advantageously used in the construction of luminescent solar concentrators (LSC). Furthermore, said benzohetero[1,3]diazole compound disubstituted with heteroaryl groups can be advantageously used in the construction of photovoltaic devices such as, for example, photovoltaic cells, photovoltaic modules, solar cells, solar modules, on both a rigid and flexible support. Said benzohetero[1,3]diazole compound disubstituted with heteroaryl groups can also be advantageously used as a precursor of monomeric units in the preparation of semiconductor polymers.

  制备二取代杂芳并[1,3]二唑化合物的过程包括反应至少一种二取代杂芳并[1,3]二唑化合物和至少一种杂芳基化合物。具有杂芳基的二取代杂芳并[1,3]二唑化合物可优势地用于构建发光太阳能浓缩器（LSC）。此外，具有杂芳基的二取代杂芳并[1,3]二唑化合物可优势地用于构建光伏器件，例如光伏电池、光伏模块、太阳能电池、太阳能模块，均可采用刚性和柔性支撑。具有杂芳基的二取代杂芳并[1,3]二唑化合物还可优势地用作半导体聚合物制备中单体单位的前体。
• [EN] PROCESS FOR THE PREPARATION OF BENZOHETERO [ 1, 3 ] - DIAZOLE COMPOUNDS DISUBSTITUTED WITH HETEOARYL GROUPS<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE COMPOSÉS BENZOHÉTÉRO[1,3]-DIAZOLE DISUBSTITUÉ PAR DES GROUPES HÉTÉROARYLE
  申请人：ENI SPA

  公开号：WO2013021315A1

  公开（公告）日：2013-02-14

  Process for the preparation of a benzohetero [ 1, 3 ] diazole compound disubstituted with heteroaryl groups which comprises reacting at least one benzohetero [ 1, 3 ] diazole compound disubstituted with at least one heteroaryl compound. Said benzohetero [ 1, 3 ] diazole compound disubstituted with heteroaryl groups can be advantageously used in the construction of luminescent solar concentrators (LSC). Furthermore, said benzohetero [ 1, 3 ] diazole compound disubstituted with heteroaryl groups can be advantageously used in the construction of photovoltaic devices such as, for example, photovoltaic cells, photovoltaic modules, solar cells, solar modules, on both a rigid and flexible support. Said benzohetero [ 1, 3 ] diazole compound disubstituted with heteroaryl groups can also be advantageously used as a precursor of monomeric units in the preparation of semiconductor polymers.

  制备一种双取代杂芳基苯并杂二唑化合物的过程，包括将至少一种双取代杂芳基苯并杂二唑化合物与至少一种杂芳基化合物反应。该含有杂芳基苯并杂二唑化合物可以优势地用于构建发光太阳能浓缩器（LSC）。此外，该含有杂芳基苯并杂二唑化合物可以优势地用于构建刚性和柔性支撑下的光伏器件，例如光伏电池、光伏模块、太阳能电池和太阳能模块。该含有杂芳基苯并杂二唑化合物也可以优势地用作半导体聚合物制备中单体单元的前体。
• Thiophene-Benzothiadiazole Co-Oligomers: Synthesis, Optoelectronic Properties, Electrical Characterization, and Thin-Film Patterning
  作者：Manuela Melucci、Laura Favaretto、Alberto Zanelli、Massimiliano Cavallini、Alessandro Bongini、Piera Maccagnani、Paolo Ostoja、Gwennaelle Derue、Roberto Lazzaroni、Giovanna Barbarella

  DOI：10.1002/adfm.200901424

  日期：2010.2.8

  the insertion of a single electron‐deficient B unit into the aromatic backbone strongly affects the LUMO energy level. The insertion of additional B units has only a minor effect on the electronic properties. Cast films of oligomers with two alternated B rings (B–T–B inner core) display crystalline order. Bottom‐contact FETs based on films cast on bare SiO2 show hole‐charge mobilities of 1 × 10−3–5 × 10−3 cm2

  据报道，新合成的噻吩（T）和苯并噻二唑（B）的共聚体具有不同的大小，交替基序和烷基取代类型。结合光谱数据，电化学分析和理论计算表明，将单个缺电子的B单元插入芳族主链会强烈影响LUMO能级。插入额外的B单元对电子性能的影响很小。具有两个交替的B环（B–T–B内芯）的低聚物的流延膜显示结晶顺序。基于在裸露的SiO 2上流延的薄膜的底部接触FET的空穴电荷迁移率为1×10 -3 –5×10 -3  cm 2 V -1 s -1和I开/关比例为10 5 –10 6。环己基取代的化合物的溶液浇铸膜是无定形的，没有FET行为。但是，可以通过纳米摩擦和非常规的湿法光刻技术克服这些薄膜中观察不到的有序性，从而可以精细控制薄沉积物中的结构有序性。
• Liquid-Crystalline Rigid-Core Semiconductor Oligothiophenes: Influence of Molecular Structure on Phase Behaviour and Thin-Film Properties
  作者：Manuela Melucci、Laura Favaretto、Christian Bettini、Massimo Gazzano、Nadia Camaioni、Piera Maccagnani、Paolo Ostoja、Magda Monari、Giovanna Barbarella

  DOI：10.1002/chem.200701368

  日期：2007.12.17

  The design, synthesis and properties of liquid-crystalline semiconducting oligothiophenes containing dithienothiophene (DTT), benzothiadiazole (BTZ) and carbazole (CBZ) rigid cores are described. The effect of molecular structure (shape, size and substitution) on their thermal behaviour and electrical properties has been investigated. Polarised optical microscopy (POM) and differential scanning calorimetry

  描述了包含二噻吩并噻吩（DTT），苯并噻二唑（BTZ）和咔唑（CBZ）刚性核的液晶半导体低聚噻吩的设计，合成和性能。已经研究了分子结构（形状，大小和取代）对其热行为和电性能的影响。偏振光学显微镜（POM）和差示扫描量热法（DSC）分析表明，大多数新合成的化合物都具有高度有序的近晶中间相。在各种温度下进行的X射线衍射（XRD）研究表明，近晶阶在冷却至转变温度时保持为结晶态，从而为流延膜提供了更有利的FET应用形态。
• Luminescent solar concentrator comprising disubstituted benzothiadiazole compounds
  申请人：ENI S.p.A.

  公开号：EP2557606A1

  公开（公告）日：2013-02-13

  Luminescent solar concentrator (LSC) comprising at least one disubstituted benzothiadiazole compound having general formula (I): wherein: - R1, R2, R3, R4, R5, R6 and R7, equal to or different from each other, represent a hydrogen atom; or they are selected from linear or branched C1-C20, preferably C1-C10, alkyl groups, cycloalkyl groups optionally substituted, aryl groups optionally substituted, linear or branched C1-C20, preferably C1-C10, alkoxyl groups, optionally substituted; - or R1 and R2, can be optionally bound to each other so as to form, together with the carbon atoms to which they are bound, a cycle or a polycyclic system containing from 3 to 14, preferably from 4 to 6 carbon atoms, saturated, unsaturated, or aromatic, optionally containing one or more heteroatoms such as, for example, oxygen, sulfur, nitrogen, silicon, phosphorous, selenium; - or R3 and R4, can be optionally bound to each other so as to form, together with the carbon atoms to which they are bound, a cycle or a polycyclic system containing from 3 to 14, preferably from 4 to 6, carbon atoms, saturated, unsaturated, or aromatic, optionally containing one or more heteroatoms such as, for example, oxygen, sulfur, nitrogen, silicon, phosphorous, selenium; - or R5 and R6, can be optionally bound to each other so as to form, together with the carbon atoms to which they are bound, a cycle or a polycyclic system containing from 3 to 14, preferably from 4 to 6, carbon atoms, saturated, unsaturated, or aromatic, optionally containing one or more heteroatoms such as, for example, oxygen, sulfur, nitrogen, silicon, phosphorous, selenium; - or R6 and R7, can be optionally bound to each other so as to form, together with the carbon atoms to which they are bound, a cycle or a polycyclic system containing from 3 to 14, preferably from 4 to 6, carbon atoms, saturated, unsaturated, or aromatic, optionally containing one or more heteroatoms such as, for example, oxygen, sulfur, nitrogen, silicon, phosphorous, selenium.

  包含至少一种具有通式 (I) 的二取代苯并噻二唑化合物的发光太阳能聚光器 (LSC)： 其中 - R1、R2、R3、R4、R5、R6 和 R7，彼此相同或不同，代表氢原子；或它们选自线性或支链 C1-C20，优选 C1-C10，烷基、任选取代的环烷基、任选取代的芳基、线性或支链 C1-C20，优选 C1-C10，任选取代的烷氧基； - 或 R1 和 R2，可以选择性地相互结合，从而与所结合的碳原子一起形成一个含有 3 至 14 个碳原子（最好是 4 至 6 个碳原子）的循环或多环体系，饱和、不饱和或芳香，可选择性地含有一个或多个杂原子，例如氧、硫、氮、硅、磷、硒； - 或 R3 和 R4 可以有选择地相互结合，以便与它们所结合的碳原子一起形成一个含有 3 至 14 个碳原子（最好是 4 至 6 个碳原子）的饱和、不饱和或芳香的循环或多环系统，可以有选择地含有一个或多个杂原子，例如氧、硫、氮、硅、磷、硒； - 或 R5 和 R6 可以有选择地相互结合，从而与它们所结合的碳原子一起形成一个含有 3 至 14 个（最好是 4 至 6 个）碳原子的饱和、不饱和或芳香的循环或多环系统，可选择地含有一个或多个杂原子，例如氧、硫、氮、硅、磷、硒； - 或 R6 和 R7 可选择性地相互结合，从而与它们所结合的碳原子一起形成一个含有 3 至 14 个（最好是 4 至 6 个）碳原子的饱和、不饱和或芳香的循环或多环系统，可选择性地含有一个或多个杂原子，例如氧、硫、氮、硅、磷、硒。