(3,4-bis(octyloxy)phenyl)boronic acid | 291753-68-9

• 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(octyloxy)phenyl)boronic acid
• 英文别名: 3,4-bis(octyloxy)phenylboronic acid；3,4-bis(octyloxyphenyl)boronic acid；3,4-dioctyloxyphenylboronic acid；(3,4-dioctoxyphenyl)boronic acid
• CAS: 291753-68-9
• 化学式: C₂₂H₃₉BO₄
• 分子量: 378.36
• InChiKey: PNDABSBCGMFBAE-UHFFFAOYSA-N

物化性质

• 沸点：
  509.1±60.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  27
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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(octyloxy)phenyl)boronic acid 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 20.0h， 生成 bis(3',4'-dioctyloxybiphenyl-4-yl)ethanedione
  参考文献：
  名称：

  Self-Assembled Fluorescent Hexaazatriphenylenes That Act as a Light-Harvesting Antenna

  摘要：

  In this paper we report the self-assembling nature of fluorescent hexaazatriphenylenes (HATs) 6a-d with six alkyl/alkoxy-chain-containing biphenyl groups and their application to light-harvesting antennae. In a nonpolar solvent and the film state, the HAT derivatives form one-dimensional aggregates with an H-type parallel stacking mode, which were analyzed by H-1 NMR, UV-vis, and steady-state and time-resolved fluorescence spectroscopy. When HAT derivative 7 with six perylenediimide moieties is incorporated into the one-dimensional aggregates, an efficient energy transfer takes place from the self-assembled HAT moiety as a light-harvesting antenna to the perylenediimide moiety as an energy acceptor. Further, when HAT derivative 8 with six triphenylamino moieties is newly added to the light-harvesting system, an intermolecular electron transfer occurs subsequently between the electron-accepting perylenediimide molecule and the electron-donating triphenylamino molecule.

  DOI：

  10.1021/jo060768n
• 作为产物：
  描述：

  1,2-二(辛氧基)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(octyloxy)phenyl)boronic 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

• 一类基于噻二唑的多环芳烃有机半导体材料 及其制备方法和在光电器件应用
  申请人：南京邮电大学

  公开号：CN106008558B

  公开（公告）日：2019-01-08

  本发明公开了一类基于噻二唑的多环芳烃有机半导体材料及其制备方法，其结构可由通式(I)表示。其中Ar表示芳基、取代芳基、杂环芳基或取代杂环芳基。本发明的杂环衍生物可以通过Suzuki偶联反应、C‑H活化偶联反应、Sonogashira偶联反应、PtCl2催化环化反应和Scholl反应合成。本发明的多环芳烃衍生物不仅具有优良的溶解性和热稳定性，并且具有优异的π共轭骨架，π共轭体系的增加有利于提高相应器件性能，是性能很好的有机半导体材料。
• Synthesis of oleophilic electron-rich phenylhydrazines
  作者：Aleksandra Jankowiak、Piotr Kaszyński

  DOI：10.3762/bjoc.8.29

  日期：——

  Phenylhydrazines 1 substituted with two or three long-chain alkyl, alkoxy or alkylsulfanyl groups were successfully prepared by acid-induced removal of the Boc group in hydrazides 2. The reaction is carried out with 5 equivalents of TfOH in CF₃CH₂OH/CH₂Cl₂ at −40 °C for 1.5 min. Under these conditions, the deprotected hydrazine 1 is fully protonated, which increases its stability in the reaction medium. The hydrazines were isolated in 60–86% yields and purities >90%. The hydrazides 2 were obtained in 43–71% yields from aryl bromides 5, which were lithiated with t-BuLi and subsequently reacted with di-tert-butyl azodicarboxylate (DTBAD).

  苯基肼1通过酸诱导去除肼酰胺2中的Boc基团，成功地取代了两个或三个长链烷基、烷氧基或烷基硫基团。反应在CF₃CH₂OH/CH₂Cl_{2>中以5当量的TfOH在-40°C下进行1.5分钟。在这些条件下，去保护的肼1被完全质子化，增加了其在反应介质中的稳定性。肼类产物以60-86%的产率和纯度>90%的纯度分离。肼酰胺2以43-71%的产率从芳基溴化物5中获得，该溴化物通过与t-BuLi锂化，然后与双tert-丁基叠氮二羧酸酯（DTBAD）反应得到。}
• Liquid crystalline behavior of tetraaryl derivatives of benzo[c]cinnoline, tetraazapyrene, phenanthrene, and pyrene: the effect of heteroatom and substitution pattern on phase stability
  作者：Monika J. Sienkowska、John M. Farrar、Fan Zhang、Sharat Kusuma、Paul A. Heiney、Piotr Kaszynski

  DOI：10.1039/b615545f

  日期：——

  A series of closely related tetrasubstituted derivatives of benzo[c]cinnoline (1), tetraazapyrene (2), phenanthrene (3), and pyrene (4) were investigated for their mesogenic properties using thermal, optical, spectroscopic, and powder XRD analyses. Only three 3,4-dioctyloxyphenyl derivatives exhibited mesogenic properties. Substitution of N for CH (3 → 1 and 4 → 2 pairs) and also increase of the core element size (1 → 2 and 3 → 4 pairs) significantly increases the mesophase stability. The findings and observed trends were rationalized by analysis of conformational properties which included calculation of the planarization energy, and modeling of aliphatic chain density and fill fractions. MO calculations showed that the tetraaza derivative 2c is significantly electron deficient and suitable for electron conductive materials.

  一系列密切相关的四取代苯并[c]吡咯啉（1）、四烯氮（2）、菲（3）和芘（4）衍生物的介质性质通过热学、光学、光谱及粉末XRD分析进行了研究。只有三种3,4-二辛氧基苯衍生物表现出了介质特性。将N替换为CH（3→1和4→2对）以及核心元素尺寸的增加（1→2和3→4对）显著提高了相位稳定性。研究结果及观察到的趋势通过对构象特性的分析进行了合理化，包括平面化能量的计算，以及脂肪链密度和填充分数的建模。分子轨道计算显示，四氮衍生物2c显著缺电子，适合用于电子导电材料。
• 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。
• Molecular design of benzothienobenzothiophene-cored columnar mesogens: facile synthesis, mesomorphism, and charge carrier mobility
  作者：Chun-Xia Liu、Hu Wang、Jun-Qi Du、Ke-Qing Zhao、Ping Hu、Bi-Qin Wang、Hirosato Monobe、Benoît Heinrich、Bertrand Donnio

  DOI：10.1039/c7tc05315k

  日期：——

  UV/Vis absorption and photoluminescence spectra, measured in both solution and films, revealed strong photoluminescence with high quantum yields. The charge carrier mobility measured by the time-of-flight (TOF) technique showed a balanced ambipolar hole and electron mobility in the range of 10−3 cm2 V−1 s−1 between 100 and 230 °C in the mesophase. These BTBT-based columnar liquid crystals may represent

  苯并噻吩并苯并噻吩（BTBT）液晶半导体由于其长程有序，自组织能力和高电荷载流子传输特性而引起了人们的极大兴趣。在这项工作中，我们报告了通过连续的Suzuki交叉偶联和FeCl 3对包含BTBT亚结构的同源系列化合物进行设计和直接合成的过程。氧化Scholl环脱氢反应。从偏光显微镜（POM），差示扫描量热法（DSC）和小角X射线散射推论得出，目标π共轭芳族H形卫生型介晶在很宽的温度范围内自组织成经典的六角柱状中间相SAXS）调查。在溶液和薄膜中测得的UV / Vis吸收和光致发光光谱显示出具有高量子产率的强光致发光。通过飞行时间（TOF）技术测量的载流子迁移率显示出平衡的双极性空穴和电子迁移率，范围为10 -3 cm 2 V -1 s -1中间相温度在100至230°C之间。这些基于BTBT的柱状液晶可以代表将被引入一维有机光电器件中的有吸引力的候选物。