4,7-bis(4-methylthiophen-2-yl)benzo[c][1,2,5]thiadiazole | 1201212-94-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 4,7-bis(4-methylthiophen-2-yl)benzo[c][1,2,5]thiadiazole
• 英文别名: TBT-4；4,7-bis(4-methylthiophen-2-yl)benzo[1,2,5]thiadiazole；Dithiophene-benzothiazole；4,7-bis(4-methylthiophen-2-yl)-2,1,3-benzothiadiazole
• CAS: 1201212-94-3
• 化学式: C₁₆H₁₂N₂S₃
• 分子量: 328.483
• InChiKey: OYAHITSGBBWUEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,7-bis(4-methylthiophen-2-yl)benzo[c][1,2,5]thiadiazole 在 zinc diacetate 、 三氯氧磷 作用下， 以 甲醇 、 氯仿 、 丙酸 、 1,2-二氯乙烷 为溶剂， 反应 30.0h， 生成 [(4-methylthiophen-5-formyl-2-yl)benzo[1,2,5]thiadiazol-4-yl]-4-methylthiophene-2-10,15,20-tris(4-methylphenyl)porphyrin zinc
  参考文献：
  名称：

  Porphyrins modified with a low-band-gap chromophore for dye-sensitized solar cells

  摘要：

  Two novel porphyrin dyes (PMBTZ and PHBTZ) modified with alkyl-thiophene and 2,1,3-benzothiadiazole (BTZ) moieties were designed and synthesized. The optical and electrochemical properties were characterized by UV-visible, fluorescence spectroscopy and cyclic voltammetry. With the introduction of the low-band-gap chromophore onto the porphyrins, the absorption spectra of the two porphyrin dyes in the range of 450-600 nm were broadened and the maximum wavelength was red-shifted compared with P-Zn as expected. The first oxidation potentials (E-ox1) were altered to the negative, which lowered from 1.27 to 1.11 and 1.15 eV, respectively. For a typical solar cell device based on dye PMBTZ, the maximal monochromatic incident photon-to-current conversion efficiency (IPCE) can reach to 65%, with a broad respondent region of 350-800 nm. Under standard global AM 1.5 solar condition, the dye-sensitized solar cell (DSSC) based on the dye PMBTZ showed the best photovoltaic performance: a short-circuit photocurrent density (J(sc)) of 14.11 mA/cm(2), an open-circuit photo voltage (V-oc) of 0.59 V, and a fill factor (ff) of 0.66, corresponding to solar-to-electric power conversion efficiency (eta) of 5.46%. (c) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2011.12.014
• 作为产物：
  描述：

  4,7-二溴-2,1,3-苯并噻二唑 、 tributyl(4-methylthiophen-2-yl)stannane 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以0.86 g的产率得到4,7-bis(4-methylthiophen-2-yl)benzo[c][1,2,5]thiadiazole
  参考文献：
  名称：

  Porphyrins modified with a low-band-gap chromophore for dye-sensitized solar cells

  摘要：

  Two novel porphyrin dyes (PMBTZ and PHBTZ) modified with alkyl-thiophene and 2,1,3-benzothiadiazole (BTZ) moieties were designed and synthesized. The optical and electrochemical properties were characterized by UV-visible, fluorescence spectroscopy and cyclic voltammetry. With the introduction of the low-band-gap chromophore onto the porphyrins, the absorption spectra of the two porphyrin dyes in the range of 450-600 nm were broadened and the maximum wavelength was red-shifted compared with P-Zn as expected. The first oxidation potentials (E-ox1) were altered to the negative, which lowered from 1.27 to 1.11 and 1.15 eV, respectively. For a typical solar cell device based on dye PMBTZ, the maximal monochromatic incident photon-to-current conversion efficiency (IPCE) can reach to 65%, with a broad respondent region of 350-800 nm. Under standard global AM 1.5 solar condition, the dye-sensitized solar cell (DSSC) based on the dye PMBTZ showed the best photovoltaic performance: a short-circuit photocurrent density (J(sc)) of 14.11 mA/cm(2), an open-circuit photo voltage (V-oc) of 0.59 V, and a fill factor (ff) of 0.66, corresponding to solar-to-electric power conversion efficiency (eta) of 5.46%. (c) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2011.12.014

文献信息

• P-TYPE SEMICONDUCTING POLYMERS AND RELATED METHODS
  申请人：AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH

  公开号：US20150349257A1

  公开（公告）日：2015-12-03

  There is provided p-type organic polymers of general formula I. The polymers may be useful as semi-conducting material. Thus, thin films and devices comprising such polymers are also provided.

  提供了一种通式为I的p型有机聚合物。该聚合物可用作半导体材料。因此，还提供了包括这种聚合物的薄膜和器件。
• Tuning the Aggregates of Thiophene‐based Trimers by Methyl Side‐chain Engineering for Photocatalytic Hydrogen Evolution
  作者：Xiaojiao Yuan、Kunran Yang、Chloé Grazon、Cong Wang、Lorenzo Vallan、Jean‐David Isasa、Pedro M. Resende、Fanxing Li、Cyril Brochon、Hynd Remita、Georges Hadziioannou、Eric Cloutet、Jian Li

  DOI：10.1002/anie.202315333

  日期：2024.1.2

  Organic π‐conjugated semiconductors (OCSs) have recently emerged as a promising alternative to traditional inorganic materials for photocatalysis. However, the aggregation of OCSs in photocatalytic aqueous solution caused by self‐assembly, which closely relates to the photocatalytic activity, has not yet been studied. Here, the relationship between the aggregation of 4,7‐Bis(thiophen‐2‐yl) benzothiadiazole (TBT) and the photocatalytic activity was systematically investigated by introducing and varying the position of methyl side chains on the two peripheral thiophene units. Experimental and theoretical results indicated that the introduction of ‐CH₃ group at the 3‐position of TBT resulted in the smallest size and best crystallinity of aggregates compared to that of TBT, 4‐ and 5‐positions. As a result, TBT‐3 exhibited an excellent photocatalytic activity towards H₂ evolution, ascribed to the shorten charge carrier transport distance and solid long‐range order. These results suggest the important role of aggregation behavior of OCSs for efficient photocatalysis.

  摘要 有机π-共轭半导体（OCSs）近来已成为光催化传统无机材料的一种有前途的替代材料。然而，OCSs 在光催化水溶液中因自组装而引起的聚集与光催化活性密切相关，目前尚未对此进行研究。本文通过引入和改变两个外围噻吩单元上甲基侧链的位置，系统研究了 4,7-双（噻吩-2-基）苯并噻二唑（TBT）的聚集与光催化活性之间的关系。实验和理论结果表明，与 TBT、4 位和 5 位相比，在 TBT 的 3 位引入 -CH3 基团可使聚合体的尺寸最小，结晶度最高。因此，TBT-3 对 H2 的演化具有极佳的光催化活性，这归因于电荷载流子传输距离缩短和固体长程有序。这些结果表明，OCS 的聚集行为对于高效光催化具有重要作用。
• COPOLYMER AND POLYMER LIGHT-EMITTING ELEMENT USING THE SAME
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2289966A1

  公开（公告）日：2011-03-02

  A copolymer having a block (A') composed of a repeating unit represented by the formula (I-1), and/or a block (A) containing a repeating unit represented by the formula (I-1) and a repeating unit represented by the formula (II). (wherein X1, X2 and X3 may be the same or mutually different and represent an oxygen atom, a sulfur atom or C(R7)=C(R8)-, and R1, R2, R3, R4, R5, R6, R7 and R8 may be the same or mutually different and represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, a mono-valent heterocyclic group, a heterocyclic thio group, an amino group, a silyl group, an acyl group, an acyloxy group, an imine residue, an amide group, an acid imide group, a carboxyl group, a cyano group or a nitro group, and m and n may be the same or mutually different and represent 2 or 3. A plurality of R1s may be the same or mutually different. A plurality of R2s may be the same or mutually different. A plurality of R5s may be the same or mutually different. A plurality of R6s may be the same or mutually different. A plurality of X1s may be the same or mutually different. A plurality of X3s may be the same or mutually different.)         -(Ar1)-     (II) (wherein Ar1 represents an arylene group.).

  一种共聚物，其嵌段 (A') 由式 (I-1) 所代表的重复单元组成，和/或嵌段 (A) 包含式 (I-1) 所代表的重复单元和式 (II) 所代表的重复单元。 芳烷基硫基、芳基烯基、芳基炔基、单价杂环基、杂环硫基、氨基、硅烷基、酰基、酰氧基、亚胺残基、酰胺基、酸亚胺基、羧基、氰基或硝基，且 m 和 n 可以相同或互异，并代表 2 或 3。多个 R1 可以相同或互不相同。多个 R2 可以相同或互不相同。多个 R5 可以相同或互异。多个 R6 可以相同或互异。多个 X1 可以相同或互异。多个 X3 可以相同或互不相同。） -(Ar1)-(II) (其中 Ar1 代表芳烯基）。
• P-type semiconducting polymers and related methods
  申请人：AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH

  公开号：US10439141B2

  公开（公告）日：2019-10-08

  There is provided p-type organic polymers of general formula I. The polymers may be useful as semi-conducting material. Thus, thin films and devices comprising such polymers are also provided.

  本文提供了通式 I 的 p 型有机聚合物。这些聚合物可用作半导电材料。因此，还提供了包含这种聚合物的薄膜和器件。
• COPOLYMER AND POLYMER LIGHT EMITTING DEVICE USING THE SAME
  申请人：Goto Osamu

  公开号：US20110127512A1

  公开（公告）日：2011-06-02

  A copolymer having a block (A′) composed of a repeating unit represented by the formula (I-1), and/or a block (A) containing a repeating unit represented by the formula (I-1) and a repeating unit represented by the formula (II). (wherein X 1 , X 2 and X 3 may be the same or mutually different and represent an oxygen atom, a sulfur atom or C(R 7 )═C(R 8 )—, and R 1 , R 2 , R 2 , R 4 , R 5 , R 6 , R 7 and R 8 may be the same or mutually different and represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, a mono-valent heterocyclic group, a heterocyclic thio group, an amino group, a silyl group, an acyl group, an acyloxy group, an imine residue, an amide group, an acid imide group, a carboxyl group, a cyano group or a nitro group, and m and n may be the same or mutually different and represent 2 or 3. A plurality of R 1 s may be the same or mutually different. A plurality of R 2 s may be the same or mutually different. A plurality of R 5 s may be the same or mutually different. A plurality of R 6 s may be the same or mutually different. A plurality of X 1 s may be the same or mutually different. A plurality of X 3 s may be the same or mutually different.) —(Ar 1 )—  (II) (wherein Ar 1 represents an arylene group.).