3,4-bis(hexyloxy)phenylboronic acid | 200959-52-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,4-bis(hexyloxy)phenylboronic acid
• 英文别名: (3,4-Bis(hexyloxy)phenyl)boronic acid；(3,4-dihexoxyphenyl)boronic acid
• CAS: 200959-52-0
• 化学式: C₁₈H₃₁BO₄
• 分子量: 322.253
• InChiKey: LUGSWAKLXIOTAT-UHFFFAOYSA-N

物化性质

• 熔点：
  129.0-129.5 °C
• 沸点：
  460.7±55.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-bis(hexyloxy)phenylboronic acid 在 iron(III) chloride 、 sodium tungstate (VI) dihydrate 、 双氧水 、 碳酸氢钠 、 sodium carbonate 、 三苯基膦 、 palladium dichloride 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 73.0h， 生成
  参考文献：
  名称：

  使用刚性核心氮氧化物自旋探针通过 EPR 光谱探测柱状盘状液晶

  摘要：

  EPR 研究盘状液晶：使用新型刚性核心硝基氧自旋探针（见图）将 EPR 光谱应用于柱状盘状液晶是可能的。在不同温度下测量的六（正己氧基）苯并菲的三相的 EPR 光谱显示出对相组成、分子旋转动力学和柱状有序的强烈敏感性。

  DOI：

  10.1002/anie.201303194
• 作为产物：
  描述：

  1,2-二己氧基苯 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 硼酸三异丙酯 、 silica gel 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 3,4-bis(hexyloxy)phenylboronic acid
  参考文献：
  名称：

  Facile Bottom-Up Synthesis of Coronene-based 3-Fold Symmetrical and Highly Substituted Nanographenes from Simple Aromatics

  摘要：

  A facile and efficient self-sorting assemble (CSA) strategy has been paved for bottom-up construction of the 3-fold symmetrical and highly substituted hexa-cata-hexabenzocoronenes (c-HBCs), the trithieno analogues, and larger disc-shaped PAHs from simple chemicals using benzylic carbons as tenon joints and a novel FeCl3-mediated AAA process as a key step. The structures of the as-prepared c-HBCs and related NGs were clearly identified by spectral analyses and X-ray crystallographic studies. Moreover, these can be envisaged to serve as new launching platforms for the construction of larger and more complex g-conjugated molecules and supramolecular architectures because of the modifiable and symmetrical decorations.

  DOI：

  10.1021/ja413018f

文献信息

• Synthesis of Extended Triphenylenes by Palladium-Catalyzed [2+2+2] Cycloaddition of Triphenylynes
  作者：Carmen Romero、Diego Peña、Dolores Pérez、Enrique Guitián

  DOI：10.1002/chem.200600466

  日期：2006.7.24

  The synthesis of ortho-(trimethylsilyl)triphenylenyl triflates 7 is described. Fluoride-induced decomposition of these triflates leads to the generation of didehydrotriphenylenes (triphenylynes) 6. These arynes undergo [4+2] cycloadditions with dienes to afford the corresponding Diels-Alder adducts or palladium-catalyzed formal [2+2+2] cycloadditions to afford extended triphenylenes.

  描述了邻-（三甲基甲硅烷基）三亚苯基三氟甲磺酸酯7的合成。氟化物引起的这些三氟甲磺酸酯的分解导致二氢三亚苯基（三苯炔）的生成。这些芳烃与二烯进行[4 + 2]环加成反应，得到相应的Diels-Alder加合物或钯催化的正式[2 + 2 + 2]环加成反应。得到扩展的亚苯基。
• Convenient synthesis of a discotic side group liquid crystal polymer
  作者：David Stewart、Gillian S. Mchattie、Corrie T. Imrie

  DOI：10.1039/a705378i

  日期：——

  The synthesis of a discotic side group liquid crystal polymer based on poly(methyl methacrylate) is reported. This involves the oxidative coupling of 3,3′,4,4′-tetrakis(hexyloxy)biphenyl with 1-hexyloxy-2-methoxybenzene to yield the unsymmetrical triphenylene nucleus, 2-methoxy-3,6,7,10,11-pentakis(hexyloxy)triphenylene. Subsequent demethylation followed by reactions first with 1,11-dibromoundecane and then with the potassium salt of methacrylic acid yielded the polymerisable monomer, 11-[3,6,7,10,11-pentakis(hexyloxy)-2-oxytriphenylene]undecyl methacrylate. This was polymerised in benzene using azoisobutyronitrile as the initiator. The thermal properties of the resulting polymer are described.

  报道了一种基于聚（甲基丙烯酸甲酯）的盘状侧基液晶聚合物的合成。这涉及到3,3′,4,4′-四己氧基联苯与1-己氧基-2-甲氧基苯的氧化偶联，生成不对称的三苯烯核2-甲氧基-3,6,7,10,11-五己氧基三苯烯。随后的去甲基化反应，先与1,11-二溴十一烷反应，再与丙烯酸钾盐反应，得到可聚合的单体11-[3,6,7,10,11-五己氧基-2-氧三苯烯]十一烷基甲基丙烯酸酯。该单体在苯中以偶氮异丁腈作为引发剂进行聚合。文中描述了所得聚合物的热性能。
• Synthesis of Crown Ether-Linked Discotic Triphenylenes
  作者：Juanjuan Li、Zhiqun He、Hemant Gopee、Andrew N Cammidge

  DOI：10.1021/ol902637z

  日期：2010.2.5

  triphenylene dimers linked by a central crown ether core have been synthesized and characterized. The crown ether is most conveniently formed as a final step to permit purification and isolation of ion-free material, and extension of the protocol permits synthesis of triad structures linked though a 27-crown-9 macrocycle. The latter compounds present a new discotic motif that supports mesophase formation.

  已经合成并表征了通过中央冠醚核连接的新型三亚苯基二聚体。冠醚最方便地形成为最终步骤，以纯化和分离无离子物质，并且该方案的扩展允许合成通过27冠9大环连接的三单元组结构。后者化合物呈现出支持中间相形成的新盘状基序。
• Synthesis and Characterization of Liquid‐Crystalline Tetraoxapentacene Derivatives Exhibiting Aggregation‐Induced Emission
  作者：Lana K. Hiscock、Brooke M. Raycraft、Monika Wałęsa‐Chorab、Coralie Cambe、Alexandre Malinge、W. G. Skene、Hi Taing、S. Holger Eichhorn、Louise N. Dawe、Kenneth E. Maly

  DOI：10.1002/chem.201804215

  日期：——

  characterization showed that these compounds exhibit aggregation‐induced emission in solution, emission in nonpolar solvents, weak emission in polar solvents, and strong emission in the solid state both as powder and in thin films. These observations are consistent with a weakly emissive charge‐transfer state in polar solvents and a more highly emissive locally excited state in nonpolar solvents.

  通过使合适的三苯基二醇与四氟对苯二甲腈以高收率反应制得一系列新的四（二烷氧基苯基）二氰基四氧杂戊并五烯衍生物（1a – c）。带有己氧基和癸氧基侧链的化合物1b和1c表现出柱状六方中间相，如偏光显微镜，变温粉末X射线衍射和差示扫描量热法所示。甲氧基取代的1 a的单晶X射线衍射揭示了二氰基四氧杂戊并五烯核是高度平面的，这与这些分子能够以柱状中间相堆叠的观念相一致。详细的光物理特征表明，这些化合物在溶液中表现出聚集诱导的发射，在非极性溶剂中发射，在极性溶剂中发射弱，并且以粉末和薄膜形式在固态下发射强。这些观察结果与极性溶剂中的弱发射电荷转移态和非极性溶剂中的较高发射局部激​​发态相一致。
• Extended triphenylenes: synthesis, mesomorphic properties and molecularly resolved scanning tunneling microscopy images of hexakis(dialkoxyphenyl)triphenylenes and dodeca(alkoxy)tris(triphenylenylene)s
  作者：Tetsuo Yatabe、Martha A. Harbison、Johann Diedrich Brand、Manfred Wagner、Klaus Müllen、Paolo Samorí、Jürgen P. Rabe

  DOI：10.1039/b001162m

  日期：——

  Palladium-catalyzed cross-coupling between 3,4-dialkoxyphenylboronic acids (1a–d) and 2,3,6,7,10,11-hexabromotriphenylene (2) provided 2,3,6,7,10,11-hexakis[3,4-bis(alkoxy)phenyl]triphenylenes, C18H6[C6H3(OCnH2n + 1)2]6 where n = 6, 8, 10, and 12 (3a–d). Cyclodehydrogenation of the aryl-substituted triphenylenes 3a–d using ferric chloride oxidation followed by methanol reduction produced 6,6′,6″,7,7′,7″,10,10′,10″,11,11′,11″-dodecaalkoxy-2,3′:3,2″:2′,3″-tris(triphenylenylene)s, C54H18(OCnH2n + 1)12 where n = 6, 8, 10, and 12 (4a–d). The mesomorphic properties of the compounds 3a–d and 4a–d were investigated by differential scanning calorimetry (DSC) measurements, polarizing microscopy, and wide angle X-ray diffraction (WAXD). The triphenylenes 3a–d exhibited a columnar mesophase in the range of 111–126, 85–104, 74–103, and 47–101 °C, respectively. Upon oxidation of the moiety, the columnar mesophases shift to higher temperatures and exist in a much broader range of temperatures: for the tris(triphenylenylene)s 4a–d, they have been observed in the range of 180–430, 150–370, 120–322, and 104–306 °C, respectively. Finally, the self-assembly at the interface between a solution of 4c and a graphite substrate has been studied by scanning tunneling microscopy. Molecularly resolved imaging revealed a highly ordered monolayer exhibiting a two-dimensional hexagonal lattice.

  在钯催化下，3,4-二烷氧基苯硼酸（1a-d）与 2,3,6,7,10,11-六溴三亚苯（2）发生交叉偶联，生成 2,3,6,7,10,11-六[3,4-双（烷氧基）苯基]三亚苯，C18H6[C6H3(OCnH2n + 1)2]6，其中 n = 6、8、10 和 12（3a-d）。先用三氯化铁氧化，再用甲醇还原，使芳基取代的三亚苯基 3a-d 环氢化，生成了 6,6′,6″,7,7′,7″,10,10′,10″,11,11′,11″-十二烷氧基-2,3′：3,2″:2′,3″-三(三亚苯)s，C54H18(OCnH2n + 1)12，其中 n = 6、8、10 和 12 (4a-d)。通过差示扫描量热法（DSC）测量、偏光显微镜和广角 X 射线衍射（WAXD）研究了 3a-d 和 4a-d 化合物的介观性质。三亚苯基 3a-d 分别在 111-126、85-104、74-103 和 47-101 ℃ 范围内呈现柱状介相。当分子被氧化时，柱状介相会转移到更高的温度，并在更宽的温度范围内存在：三（三亚苯）4a-d 的柱状介相分别在 180-430、150-370、120-322 和 104-306 ℃ 范围内观察到。最后，我们利用扫描隧道显微镜研究了 4c 溶液与石墨基底之间界面的自组装。分子分辨成像显示出一个高度有序的单层，呈现出二维六边形晶格。