1,4-dibromo-2,5-bis(methoxymethyl)benzene | 144526-35-2

• 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: 1,4-dibromo-2,5-bis(methoxymethyl)benzene
• CAS: 144526-35-2
• 化学式: C₁₀H₁₂Br₂O₂
• 分子量: 324.012
• InChiKey: UYZHRFSZANMPME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-dibromo-2,5-bis(methoxymethyl)benzene 在 氢氧化钾 、 四(三苯基膦)钯 、 氢溴酸 、 碳酸氢钠 、 硫脲 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 甲苯 为溶剂， 反应 34.0h， 生成 6,17-Bis(9,9-diethylfluoren-2-yl)-13,15-dimethoxy-3,10-dithiatricyclo[10.2.2.25,8]octadeca-1(14),5(18),6,8(17),12,15-hexaene
  参考文献：
  名称：

  Alternating Conjugated and Transannular Chromophores:  Tunable Property of Fluorene-Paracyclophane Copolymers via Transannular π−π Interaction

  摘要：

  GraphicsA series of fluorene-dithia[3.3]paracyclophane copolymers was synthesized by Suzuki coupling reactions of suitable precursors. Transannular pi-pi interactions altered the electronic and optical properties of the polymer backbone significantly. A large red shift in the emission spectrum of the unsubstituted polymer was accompanied by enhanced photoluminescence (PL) efficiency. Substitution in the cyclophane unit resulted in PL quenching.

  DOI：

  10.1021/ol034413r
• 作为产物：
  描述：

  2,5-二溴-1,4-二甲基苯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 1,4-dibromo-2,5-bis(methoxymethyl)benzene
  参考文献：
  名称：

  Synthesis and photophysics of new pyridyl end-capped 3D-dithia[3.3]paracyclophane-based Janus tectons: surface-confined self-assembly of their model pedestal on HOPG

  摘要：

  一旦合成，这些新的构造体展示了离子键和配位键。令人惊讶的是，P形成了一个准方形自组装体，独立于基础的HOPG晶格。

  DOI：

  10.1039/d0nj00110d

文献信息

• Organoselenium-substituted poly(p-phenylenevinylene)
  作者：Nicolai Stuhr-Hansen、Edwin H. A. Beckers、Lars Engman、René A. J. Janssen

  DOI：10.1002/hc.20167

  日期：——

  A new type of conjugated polymer, organoselenium substituted poly(p-phenyleneviny- lene) (PPV), was synthesized from the corresponding alkylselenenyl p-xylylene dibromide via a Gilch route using potassium tert-butoxide in THF. The p-xylylene dibromide precursors were synthesized by reacting lithiated bis(methoxymethyl)benzenes with elemental selenium, followed by alkylation of the generated selenolates

  一种新型的共轭聚合物，有机硒取代的聚（对亚苯基乙烯基）（PPV），是由相应的烷基亚硒基对二溴化苯通过使用叔丁醇钾在 THF 中的 Gilch 路线合成的。通过将锂化的双（甲氧基甲基）苯与元素硒反应，然后将生成的硒酸盐烷基化，合成对二溴化苯前体。作为最后的去掩蔽步骤，使用三溴化硼通过醚裂解释放溴甲基官能团。获得的双烷基硒基 PPV 的平均分子量 Mw 约为 300,000 g/mol，多分散性 Mw/Mn = 2。由于溶解度低，获得的单烷基硒基 PPV 的平均分子量相当低，接近 16,000 g/mol mol，多分散性略大于 3。吸收光谱和荧光光谱表明双烷基硒基 PPV 广泛共轭。© 2005 Wiley Periodicals, Inc. 杂原子化学 16:656–662, 2005; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI
• Bedard, Thomas C.; Moore, Jeffrey S., Journal of the American Chemical Society, 1995, vol. 117, # 43, p. 10662 - 10671
  作者：Bedard, Thomas C.、Moore, Jeffrey S.

  DOI：——

  日期：——
• Electrophilic organic selenium reagents—protonated seleninic acids as precursors for unsymmetrical aromatic selenides
  作者：Nicolai Stuhr-Hansen、Theis Ivan Sølling、Lars Henriksen

  DOI：10.1016/j.tet.2011.02.004

  日期：2011.4

  Arylselenylations of methylbenzenes, methoxybenzenes and thiophene were smoothly achieved with selenenium ions generated by comproportionation of 1:1 mixtures of p-toluenesulfonic acid salts of seleninic acids and the corresponding diselenides. A series of p-toluenesulfonic salts of seleninic acids were prepared by hydrogen peroxide oxidation of the corresponding diselenides in the presence of p-toluenesulfonic acid. Novel 2-(organylseleno)thiophenes were obtained by heating the protonated seleninic acids with a 50-fold excess of thiophene in glacial acetic acid. (C) 2011 Published by Elsevier Ltd.
• Novel Synthesis of Protected Thiol End-Capped Stilbenes and Oligo(phenylenevinylene)s (OPVs)
  作者：Nicolai Stuhr-Hansen、Jørn B. Christensen、Niels Harrit、Thomas Bjørnholm

  DOI：10.1021/jo0263770

  日期：2003.2.1

  The first general procedures for preparation of thiol end-capped stilbenes and oligo(phenylene-vinylene)s (OPVs) with tert-butyl- and acetyl-protected thiol termini have been developed. These reactions proceed via Br/Li exchange, McMurry, and Wittig-type reactions. The thiol functionality is protected against strong basic and acidic reaction conditions as a t-Bu sulfide. As a key point in the method, reprotection of the thiol group is accomplished by means of acetyl chloride and boron tribromide. The novel strategy forms the basis for stepwise introduction of 4-mercaptostyryl units in OPVs. The new mono-, di-, and trimercapto OPVs have potential applications as one, two, and three terminal molecular devices in gold nanoparticle clusters, self-assembled monolayers, and optoelectronic devices.
• Alternating Aromatic and Transannular Chromophores with and without Linker:  Effect of Transannular π−π Interaction on the Optical Property of Dithiaparacyclophane-based Copolymers
  作者：Weiling Wang、Jianwei Xu、Yee-Hing Lai、Fuke Wang

  DOI：10.1021/ma035902+

  日期：2004.5.1

  A series of bithiophene-cyclophane (PPP-type), acetylene-fluorene-acetylene-cyclophane (PPE-type), and ethylene-fluorene-ethylene-cyclophane (PPV-type) copolymers, namely, 4-6, was synthesized via a nickel-catalyzed reaction, a palladium-catalyzed Sonagashira reaction, and a Heck coupling, respectively. Unlike in the fluorene-cyclophane copolymer 3, the transannular pi-pi interaction of the cylophane unit in copolymer 4 resulted in a significant blue shift in its emission spectrum compared to a reference polymer, giving it an essentially blue emitting light. By introducing an acetylene or ethylene linker in going from 3 to 5 or 6, the effective conjugation in the polymer backbone due to higher rigidity in coplanarity decreased the effect of the transannular pi-pi interaction. While the PPV-type copolymer 6 still exhibited an appreciable red shift in both absorption and emission with respect to a reference polymer, negligible shifts were observed for copolymer 5.