4,6-dibromothieno[3,4-b]thiophene | 1260686-70-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 4,6-dibromothieno[3,4-b]thiophene
• 英文别名: 4,6-dibromothieno[2,3-c]thiophene
• CAS: 1260686-70-1
• 化学式: C₆H₂Br₂S₂
• 分子量: 298.022
• InChiKey: FEXAKNVHUAEACM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4-溴噻吩-3-基)乙炔基-三甲基硅烷 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 水 作用下， 以 乙醚 、 正己烷 、 氯仿 为溶剂， 反应 6.5h， 生成 4,6-dibromothieno[3,4-b]thiophene
  参考文献：
  名称：

  Tuning the Band Gap of Low-Band-Gap Polyselenophenes and Polythiophenes: The Effect of the Heteroatom

  摘要：

  A series of new low-band-gap thieno- or selenolo-fused polyselenophenes (P5 and P6) and selenolo-fused polythiophene (P4) (as well as previously reported thieno-fused polythiophene, P3) was prepared systematically by electropolymerization (P4-P6) and by solid-state polymerization (P3, P5 and P6). The 2,5-dibrominated monomers (3Br(2), 5Br(2), and 6Br(2)) undergo solid-state polymerization under slight heating and produce insoluble P3, P5, and P6 as black conducting powders. The spectroelectrochemically measured optical band gaps of P4-P6 films are 0.96, 0.72, and 0.76 eV, respectively. DFT calculations performed on P3-P6 provide excellent estimations of the experimental band gaps of these polymers. The band gap of the polyselenophenes (P5 and P6) is 0.2 eV lower than that of the corresponding polythiophenes (P3 and P4). We introduced a new scheme for band gap control in conjugated polymers by replacing the sulfur atom with a selenium atom in the main and/or peripheral ring, which leads to significant and predictable changes in the band gap of the polymers. This is due to the lower aromaticity of a selenophene ring compared to a thiophene ring. Thus, we have achieved band gap control in very low band gap (similar to 0.7-1.0 eV) polymers through the use of different combinations of selenium and sulfur atoms in the main and peripheral rings.

  DOI：

  10.1021/cm102395v

文献信息

• CONJUGATED POLYMERS
  申请人：Blouin Nicolas

  公开号：US20140034880A1

  公开（公告）日：2014-02-06

  The invention relates to novel benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl-alt-thieno[3,4-b]thiazole-4,6-diyl polymers, methods for their preparation and monomers used therein, blends, mixtures and formulations containing them, the use of the polymers, blends, mixtures and formulations as semiconductor in organic electronic (OE) devices, especially in organic photovoltaic (OPV) devices, and to OE and OPV devices comprising these polymers, blends, mixtures or formulations.

  本发明涉及新型苯并[1,2-b:4,5-b′]噻吩-2,6-二基-α-噻吩[3,4-b]噻唑-4,6-二基聚合物，其制备方法及所使用的单体，包含它们的混合物、配方和混合物，以及将这些聚合物、混合物、配方作为半导体在有机电子（OE）器件中的使用，特别是在有机光伏（OPV）器件中的使用，以及包含这些聚合物、混合物或配方的OE和OPV器件。
• SEMICONDUCTING POLYMERS
  申请人：Merck Patent GmbH

  公开号：EP2590986A2

  公开（公告）日：2013-05-15
• US9287505B2
  申请人：——

  公开号：US9287505B2

  公开（公告）日：2016-03-15
• [EN] SEMICONDUCTING POLYMERS<br/>[FR] POLYMÈRES SEMI-CONDUCTEURS
  申请人：MERCK PATENT GMBH

  公开号：WO2012003919A2

  公开（公告）日：2012-01-12

  The invention relates to novel polymers containg repeating units based on thieno[3,4-b]thiophene, monomers and methods for their preparation, their use as semiconductors in organic electronic (OE) devices, especially in organic photovoltaic (OPV) devices, and to OE and OPV devices comprising these polymers.
• [EN] CONJUGATED POLYMERS<br/>[FR] POLYMÈRES CONJUGUÉS
  申请人：MERCK PATENT GMBH

  公开号：WO2012143081A1

  公开（公告）日：2012-10-26

  The invention relates to novel benzo[1,2-b:4,5-b']dithiophene-2,6-diyl-alt- thieno[3,4-b]thiazole-4,6-diyl polymers, methods for their preparation and monomers used therein, blends, mixtures and formulations containing them, the use of the polymers, blends, mixtures and formulations as semiconductor in organic electronic (OE) devices, especially in organic photovoltaic (OPV) devices, and to OE and OPV devices comprising these polymers, blends, mixtures or formulations.