(4'-formylbiphenyl-4-yl)boronic acid

• 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: (4'-formylbiphenyl-4-yl)boronic acid
• 英文别名: (4’-formyl-[1,1’-biphenyl]-4-yl)boronic acid；(4'-formyl-[1,1'-biphenyl]-4-yl)boronic acid；4-(4-formylphenyl)phenyl-boronic acid；4'-formylbiphenyl-4-boronic acid；4-(4-Formylphenyl)phenylboronic acid；[4-(4-formylphenyl)phenyl]boronic acid
• 化学式: C₁₃H₁₁BO₃
• 分子量: 226.04
• InChiKey: GSTOVMGVTCXLDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4'-formylbiphenyl-4-yl)boronic acid 在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， 反应 12.5h， 生成 (4'-(4-(dimethylamino)pyridin-3-yl)-[1,1'-biphenyl]-4-yl)methanol
  参考文献：
  名称：

  手性配位胶囊外部催化仲醇的动力学拆分

  摘要：

  分子主体内部手性空间的限制是对映选择性反应的理想平台。然而，这个概念极大地限制了反应物的范围，因为反应物必须被捕获在分子主体内。相反，我们利用手性分子胶囊的外部作为手性源，实现了仲醇的动力学拆分。

  DOI：

  10.1002/chem.202304244
• 作为产物：
  描述：

  4’-溴-[1,1’-联苯]-4-甲醛 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 21.5h， 生成 (4'-formylbiphenyl-4-yl)boronic acid
  参考文献：
  名称：

  Cyclic Thiourea/Urea Functionalized Triphenylamine-Based Dyes for High-Performance Dye-Sensitized Solar Cells

  摘要：

  Six cyclic thiourea/urea functionalized triphenylamine-based dyes (AZ1-AZ6) containing 2-cyanoacrylic acid as an acceptor and various linkers (phenyl, biphenyl, and bithiophene) were synthesized. They exhibited high photovoltaic performance owing to an improved short-circuit photocurrent density (J(sc)) and open-circuit voltage (V-oc). Among them, AZ6 bearing a cyclic thiourea group and bithiophene linker showed the highest power conversion efficiency (PCE) up to 7.29%, which was comparable to that of N719 (PCE = 7.36%).

  DOI：

  10.1021/ol4001685

文献信息

• Icli, Burcak; Christinat, Nicolas; Toennemann, Justus, Journal of the American Chemical Society, 2009, vol. 131, p. 3154 - 3155
  作者：Icli, Burcak、Christinat, Nicolas、Toennemann, Justus、Schuettler, Christian、Scopelliti, Rosario、Severin, Kay

  DOI：——

  日期：——
• Palladium supported on aminopropyl-functionalized polymethylsiloxane microspheres: Simple and effective catalyst for the Suzuki–Miyaura C–C coupling
  作者：Wojciech Zawartka、Piotr Pośpiech、Marek Cypryk、Anna M. Trzeciak

  DOI：10.1016/j.molcata.2015.07.002

  日期：2015.10

  A palladium catalyst, obtained in the reaction of PdCl2(MeCN)(2) with microspheric aminopropyl polymethylsiloxane, was used in the Suzuki Miyaura cross-coupling of various aryl bromides with phenylboronic acids. Catalytic reactions, performed at 80 degrees C in a 2-propanol/water mixture, led to high yields of non-symmetric biphenyls. In recycling experiments, excellent results (up to 100%) were obtained in ten subsequent runs. Efficient separation of the catalyst from organic products was achieved by simple filtration due to the properties of microspheres. (C) 2015 Elsevier B.V. All rights reserved.
• Three-Dimensional Four-Connecting Organic Scaffolds with a Twist:  Synthesis and Self-Assembly
  作者：Jarugu Narasimha Moorthy、Ramalingam Natarajan、Paloth Venugopalan

  DOI：10.1021/jo051205z

  日期：2005.10.1

  We have synthesized a novel class of four-connecting three-dimensional molecular scaffolds 2-5 based on biaryls for supramolecular self-assembly. The X-ray crystal structure analysis of 2 with ethanol reveals a novel O-H center dot center dot center dot O hydrogen-bonded helical self-assembly in three dimensions leading to the generation of channels in the crystal lattice, The tetraacid 3 also forms analogous channels in which the solvent molecules, viz., DMSO and H2O, reside. The structures of 2 and 3 amply illustrate the potential of three-dimensional four-connecting biaryls in developing functional mimics of inorganic zeolites.
• Nondoped Pure-Blue OLEDs Based on Amorphous Phenylenevinylene-Functionalized Twisted Bimesitylenes
  作者：Jarugu Narasimha Moorthy、Parthasarathy Venkatakrishnan、Palani Natarajan、Zhenghuan Lin、Tahsin J. Chow

  DOI：10.1021/jo1001565

  日期：2010.4.16

  The twisted bimesitylene scaffold hinders crystallization and imparts amorphous nature to the oligophenylenevinylenes (OPVs) generated by 2- and/or 4-fold functionalization. The resultant phenylenevinylenes 1-5 with unique molecular topology exhibit excellent thermal and solid-state luminescence properties. The amorphous nature permits their application as pure-blue emissive materials in OLEDs. Under nondoped conditions, the device performances observed surpass those for analogous and simple oligophenylenevinylenes known so far; for example, the device based on OPV 2 as an emitting material and structurally analogous Bim-DPAB as a hole-transporting material yields pure-blue electroluminescence with an external quantum efficiency of ca. 4.70% at 20 mA/cm(2), which is higher than those reported for nondoped pure-blue OPV emitters.
• Self-Organization of Bent Rod Molecules into Hexagonally Ordered Vesicular Columns
  作者：Ho-Joong Kim、Feng Liu、Ja-Hyoung Ryu、Seong-Kyun Kang、Xiangbing Zeng、Goran Ungar、Jeong-Kyu Lee、Wang-Cheol Zin、Myongsoo Lee

  DOI：10.1021/ja3060904

  日期：2012.8.22

  Bent-shaped rigid-core molecules with flexible chiral dendrons grafted to the outer side of the bend were synthesized and characterized by circular dichroism, differential scanning calorimetry, X-ray scatterings, and transmission electron microscopy in solution and the solid state. The bent aromatic rods based on hepta- and nonaphenylene with nitrile groups at both ends self assemble into well ordered hollow tubular structures in aqueous solution, while the bent rod based on heptaphenylene Without nitrile groups showed no apparent. aggregations in aqueous solution. In the solid state, the rigid-flexible molecules based on heptaphenylene rod without the nitrile group self-assemble into a 2D oblique columnar structure with the columnar cross-section containing two interlocked molecules.. Remarkably, the rigid flexible molecules based on hepta-, nona-, and undecaphenylene with nitrile groups elf-assemble: into a-hexagonal columnar structure With weak 3D order. A model of vesicular channel structure is proposed based on small- and wide- angle X-ray diffraction on oriented fibers, density measurement, reconstruction and simulation of electron density maps, and molecular dynamics simulation. In contrast to the hollow tubular structure found in solution, in the solid both the outside and the interior of the columns are filled by the pendant aliphatic coils. Filling of the interior of these vesicular channels is Made. possible by some bent rod molecules turning their obtuse apex inward. One in 7, 2 in 8, and 4 in 10 molecules are thus inverted in a column slice in compounds with hepta-, nona-, and undecaphenylene cores, respectively. These are new examples of vesicular double-segregated columnar structures recently discovered in some dendrons.