1-bromo-4,5-bis(bromomethyl)-2-methoxybenzene | 1207065-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-bromo-4,5-bis(bromomethyl)-2-methoxybenzene
• CAS: 1207065-35-7
• 化学式: C₉H₉Br₃O
• 分子量: 372.882
• InChiKey: YFYMFDXIXDCFGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-bromo-4,5-bis(bromomethyl)-2-methoxybenzene 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium hydride 、 tri tert-butylphosphoniumtetrafluoroborate 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  WO2023/42914

  摘要：

  公开号：
• 作为产物：
  描述：

  3,4-二甲基茴香醚 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 1-bromo-4,5-bis(bromomethyl)-2-methoxybenzene
  参考文献：
  名称：

  Effects of Solubilizing Group Modification in Fullerene Bis-Adducts on Normal and Inverted Type Polymer Solar Cells

  摘要：

  Structural control of solubilizing side groups in fullerene-based electron acceptors is critically important to optimize their performance in bulk heterojunction (BHJ)-type polymer solar cell (PSC) devices. The structural changes of fullerene derivatives affect not only their optical and electrochemical properties but also their solubility and miscibility with electron donor polymers. Herein, we synthesized a series of o-xylenyl C-60 bis-adduct (OXCBA) derivatives with different solubilizing side groups to systematically investigate the effects of fullerene derivative structures on the photovoltaic properties of PSCs. The xylenyl side groups on the OXCBA were modified to produce several different OXCBA derivatives in which the xylenyl groups were functionalized with fluorine (FXCBA), nitro (NXCBA), methoxy and bromine (BMXCBA), and phenyl groups (ACBA). End group modifications of OXCBA dramatically affect photovoltaic performance in blend films with poly(3-hexylthiophene) (P3HT), resulting in power conversion efficiencies (PCEs) ranging from 1.7 to 5.3%. We found that this large range in PCE values is mainly due to differences in the blend morphology and interfacial area of the P3HT:OXCBA derivative films caused by changes in the hydrophobicity of the OXCBA derivatives and their interaction with P3HT. The trend in photovoltaic performance of the different OXCBA derivatives agrees well with those of the interfacial tension, PL quenching, and exciton dissociation probability, which suggests that changes in the interaction with P3HT are largely responsible for their photovoltaic performances. Finally, the OXCBA derivatives were applied in inverted type PSC devices. We note that P3HT:OXCBA blend devices exhibited more than 5% PCE with excellent air stability, which is one of the best inverted type devices based on the P3HT polymer in a simple device architecture without any extra interlayers.

  DOI：

  10.1021/cm3010369

文献信息

• Synthesis of the Conformationally Constrained Tyrosine Analogues, (<i>R</i>)- and (<i>S</i>)-5-Hydroxy-2-aminoindan-2-carboxylic Acids
  作者：Francis N. Murigi、Gary S. Nichol、Eugene A. Mash

  DOI：10.1021/jo902438s

  日期：2010.2.19

  The conformationally constrained tyrosine analogues, (R)- and (S)-5-hydroxy-2-aminoindan-2-carboxylic acids, were prepared by chromatographic separation of diastereomeric dipeptide derivatives formed from N-BOC-L-phenylalanine. Absolute configurations were assigned by X-ray crystallographic analysis.
• Effects of Solubilizing Group Modification in Fullerene Bis-Adducts on Normal and Inverted Type Polymer Solar Cells
  作者：Ki-Hyun Kim、Hyunbum Kang、Hyeong Jun Kim、Pan Seok Kim、Sung Cheol Yoon、Bumjoon J. Kim

  DOI：10.1021/cm3010369

  日期：2012.6.26

  Structural control of solubilizing side groups in fullerene-based electron acceptors is critically important to optimize their performance in bulk heterojunction (BHJ)-type polymer solar cell (PSC) devices. The structural changes of fullerene derivatives affect not only their optical and electrochemical properties but also their solubility and miscibility with electron donor polymers. Herein, we synthesized a series of o-xylenyl C-60 bis-adduct (OXCBA) derivatives with different solubilizing side groups to systematically investigate the effects of fullerene derivative structures on the photovoltaic properties of PSCs. The xylenyl side groups on the OXCBA were modified to produce several different OXCBA derivatives in which the xylenyl groups were functionalized with fluorine (FXCBA), nitro (NXCBA), methoxy and bromine (BMXCBA), and phenyl groups (ACBA). End group modifications of OXCBA dramatically affect photovoltaic performance in blend films with poly(3-hexylthiophene) (P3HT), resulting in power conversion efficiencies (PCEs) ranging from 1.7 to 5.3%. We found that this large range in PCE values is mainly due to differences in the blend morphology and interfacial area of the P3HT:OXCBA derivative films caused by changes in the hydrophobicity of the OXCBA derivatives and their interaction with P3HT. The trend in photovoltaic performance of the different OXCBA derivatives agrees well with those of the interfacial tension, PL quenching, and exciton dissociation probability, which suggests that changes in the interaction with P3HT are largely responsible for their photovoltaic performances. Finally, the OXCBA derivatives were applied in inverted type PSC devices. We note that P3HT:OXCBA blend devices exhibited more than 5% PCE with excellent air stability, which is one of the best inverted type devices based on the P3HT polymer in a simple device architecture without any extra interlayers.
• WO2023/42914
  申请人：——

  公开号：——

  公开（公告）日：——