(3,4-bis(decyloxy)phenyl)boronic acid | 233661-05-7

• 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(decyloxy)phenyl)boronic acid
• 英文别名: 3,4-(di(decyloxy)phenyl)boronic acid；(3,4-Didecoxyphenyl)boronic acid
• CAS: 233661-05-7
• 化学式: C₂₆H₄₇BO₄
• 分子量: 434.468
• InChiKey: QDZGXPIRMFSPAA-UHFFFAOYSA-N

物化性质

• 沸点：
  555.2±60.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  31
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 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(decyloxy)phenyl)boronic acid 在 四(三苯基膦)钯 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 4-(3,4-Didecyloxyphenyl)benzoic acid
  参考文献：
  名称：

  The Importance of Micro Segregation for Mesophase Formation: Thermotropic Columnar Mesophases of Tetrahedral and other Low-Aspect-Ratio Organic Materials

  摘要：

  Several low-aspect-ratio organic molecules [tetrahedral pentaerythritol derivatives, peracylated polyhydroxy compounds and aminoalcohols, a tetraphenylmethane derivative, a tetraphenylstannane, and a tetrahedral zinc bis(1,3-diketonate) all carrying long aliphatic chains] have been synthesized. These compounds were investigated by polarizing optical microscopy and differential scanning calorimetry, and some of them by X-ray diffraction. Most compounds show columnar liquid-crystalline mesophases. Their mesogenic properties are neither caused by a specific anisometric shape of these molecules nor by a strong amphiphilicity as known from conventional liquid crystals. Instead their mesogenity is mainly driven by micro segregation of the incompatible molecular parts (polar central regions and lipophilic alkyl chains) into well-organized different microdomains. It is shown that, in analogy to block copolymers, the mesophase stability rises on enlarging the number of repeat units connected with each other and on increasing the degree of incompatibility between the incompatible segments. During the process of self-organization the average conformation of the molecules is changed in such a way that it allows a most efficient packing of the molecules. Consequently, rigid molecules with a fixed tetrahedral geometry are not mesogenic. The molecules described herein can be regarded as the most simple star-shaped low-aspect-ratio block molecules that form liquid-crystalline phases. They bridge the gap between classical amphiphilic mesogens, several nonconventional dendritic and oligomeric liquid crystals, and mesomorphic block copolymers.

  DOI：

  10.1002/(sici)1521-3765(19990503)5:5<1643::aid-chem1643>3.0.co;2-t
• 作为产物：
  描述：

  1,2-(二葵氧荃)苯 在 正丁基锂 、 溴 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3,4-bis(decyloxy)phenyl)boronic acid
  参考文献：
  名称：

  Smectic and Columnar Liquid Crystalline Phases through Charge-Transfer Interactions

  摘要：

  New heterocyclic electron donors based on. a 1,3,5-triazine nucleus are presented. Three phenyl rings are grafted to the triazine core either via secondary amino groups or by a direct C,C-linkage and a specific number of decyloxy chains is attached to the molecular periphery. The compounds are non-liquid crystalline in their pure states. Lamellar or columnar mesophases are induced by attractive interactions with electron acceptors.

  DOI：

  10.1080/15421400490435369

文献信息

• Impact of Substitution Pattern and Chain Length on the Thermotropic Properties of Alkoxy-Substituted Triphenyl-Tristriazolotriazines
  作者：Thorsten Rieth、Natalie Tober、Daniel Limbach、Tobias Haspel、Marcel Sperner、Niklas Schupp、Philipp Wicker、Stefan Glang、Matthias Lehmann、Heiner Detert

  DOI：10.3390/molecules25235761

  日期：——

  Tristriazolotriazines (TTTs) with a threefold alkoxyphenyl substitution were prepared and studied by DSC, polarized optical microscopy (POM) and X-ray scattering. Six pentyloxy chains are sufficient to induce liquid-crystalline behavior in these star-shaped compounds. Thermotropic properties of TTTs with varying substitution patterns and a periphery of linear chains of different lengths, branching

  通过 DSC、偏光光学显微镜 (POM) 和 X 射线散射制备并研究了具有三重烷氧基苯基取代的三三唑并三嗪 (TTT)。六个戊氧基链足以在这些星形化合物中诱导液晶行为。比较了具有不同取代模式和不同长度的线性链外围、链中分支和燕尾的 TTT 的热致性质。一般来说，这些盘显示出广泛且稳定的热致中间相，切向 TTT 优于径向异构体。研究了烷基链的数量、位置、长度和结构的构效关系。
• 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。
• 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。
• Thermotropic Properties and Molecular Packing of Discotic Tristriazolotriazines with Rigid Substituents
  作者：Thorsten Rieth、Tomasz Marszalek、Wojciech Pisula、Heiner Detert

  DOI：10.1002/chem.201400034

  日期：2014.4.22

  liquid‐crystalline mesophase. The structural study indicates that the thermotropic properties and organization of these systems can be well tuned by the steric demand of the aryl groups. Depending on the substituents, the compounds showed either a pure crystalline phase or a highly complex helical superstructure with a characteristic liquid‐crystalline phase at elevated temperatures. Changing the steric demand

  通过氰尿酰氯和相应的四唑的惠斯根反应已经制备了具有三倍二烷氧基芳基取代的三三唑三嗪。尽管这些染料显示对UV / Vis吸收呈负性或反向溶剂化变色，但它们的荧光却是强烈的正溶剂化变色。这些盘状荧光团还以固态和宽液晶中间相发光。结构研究表明，可以通过芳基的空间需求很好地调节这些体系的热致性质和组织。根据取代基的不同，化合物在高温下会显示纯晶相或高度复杂的螺旋上层结构，并具有特征性的液晶相。