2-(4-pinacolatoboronphenyl)-3,3-diphenylacrylonitrile | 288105-07-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(4-pinacolatoboronphenyl)-3,3-diphenylacrylonitrile
• 英文别名: 3,3-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-acrylonitrile；3,3-Diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acrylonitrile；3,3-diphenyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]prop-2-enenitrile
• CAS: 288105-07-7
• 化学式: C₂₇H₂₆BNO₂
• 分子量: 407.32
• InChiKey: OZXIYAOBWRKDLC-UHFFFAOYSA-N

物化性质

• 沸点：
  522.4±50.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  四溴四苯甲烷 、 2-(4-pinacolatoboronphenyl)-3,3-diphenylacrylonitrile 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以82%的产率得到tetrakis(4,4'-(3,3-diphenylacrylonitrile)-1,1'-biphenyl)methane
  参考文献：
  名称：

  Synthesis, Morphology, and Optical Properties of Tetrahedral Oligo(phenylenevinylene) Materials

  摘要：

  A novel topological strategy is described for designing amorphous molecular solids suitable for optoelectronic applications. In this approach, chromophores are attached to a tetrahdral point of convergence. Stilbenoid units were covalently linked to tetraphenylmethane, tetraphenyladamantane, or tetraphenylsilane cores using palladium catalyzed coupling methodology, Thus, reaction of E(C6H5X)(4) (E = C and adamantane, X = I; E = Si, X = Br) with styrene or 4,3'-tert-butylvinylstilbene under Heck coupling conditions yields the corresponding tetrakis(stillbenyl) (E(STB)(4)) and tetrakis(4-tert-butyIstyrylstilbenyl) (E((BuSSB)-Bu-t)(4)) compounds. Similarly, reaction of 1,1-diphenyl-2-(4-dihydroxyboronphenyl)ethene or 2-(4-pinacolatoboronphenyl)-3,3-diphenylacrylonitrile with tetrakis(4-bromophenyl)methane using Suzuki coupling methodology gives tetrakis(4,4'-(2,2-diphenyl-vinyl)-1,1'-biphenyl (C(DPVBi)(4)) or tetrakis(4,4'-(3,3-diphenylacrylonitrile biphenyl)methane (C(DPAB)(4)), respectively, in good yields. Compounds with more extended conjugation can also be prepared. Thus, reaction of excess 1-(4'-tert-butylstyryl)-4-(4'-vinylstyryl)benzene with C(C6H4I)(4) provides tetrakis(4-(4'-(4"-tert-butylstyryl)styryl)stilbenyl)methane (C(4R-Bu-t)(4)) in low yield (similar to 20%). The more soluble analogue, tetrakis(4-(4'-(3",5"-di-tert-butylstyryl)stilbenyl)methane (C(4R-2(t)Bu)(4)) is prepared similarly using 1-(3',5'-di-tert-butylstyryl)-4-(4'-vinylstyryl)benzene and in better yield (similar to 80%). Alkoxy substituents can also be used to increase solubility. Tetrakis((4-(2',5'-dioctyloxy-4'-styryl)styryl)stilbenyl)methane methane, C(4R-(OC8H17)(2))(4), was prepared by treatment of C(C6H4I)(4) with excess 2,5-dioctyloxy-1-styryl-4(4'-vinylstyryl)benzene (yield similar to 73%). The simple stilbenyl-derivatives were found by DSC measurements and powder diffraction experiments to be crystalline compounds. Comparison of single-crystal X-ray diffraction data shows that C(STB)(4) and Si(STB)(4) form isomorphous crystals. The larger E((BuSSB)-Bu-t)4, C(DPVBi)(4), and C(DPAB)(4) compounds readily form amorphous glasses with elevated glass transition temperatures (T-g = 142-190 degrees C) in the absence of solvent. Extending the conjugation length of the arm leads to more stable glasses. For example, the glass transition temperature of C(4R-Bu-t)(4) was measured at 230 degrees C. Solution phase optical spectroscopic data of E((BuSSB)-Bu-t)(4) (E = C, adamantane, and Si) are characteristic of the parent distyrylbenzene chromophore. Films, however, show broad and significantly red-shifted emission spectra. In contrast, C(DPVBi)(4) gives absorption and emission spectra which are nearly identical between dilute solution phase samples and neat solid films. The emission of C(DPAB)(4) is broad and structureless, reminiscent of exciplex or excimer emission. Films of the tetramers with longer arms (C(4R-Bu-t)(4), C(4R-2(t)Bu)(4), and C(4R-(OC8H17)(2))(4)) show emission properties which are dependent on sample history. Annealing the sample at elevated temperature leads to red-shifted emission as a result of better interdigitation between the optically active fragments.

  DOI：

  10.1021/ja992924w
• 作为产物：
  描述：

  4-溴苯腈 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium hydride 作用下， 以 N,N-二甲基乙酰胺 、 苯 为溶剂， 生成 2-(4-pinacolatoboronphenyl)-3,3-diphenylacrylonitrile
  参考文献：
  名称：

  具有聚集诱导的发射和分子内电荷转移特性的高效固体发射体：分子设计，合成，光物理行为和OLED应用

  摘要：

  发射电子供体-受体（DA）共轭物在生物光子学，双光子吸收材料，有机激光器，长波长发射器等方面具有广泛的应用。但是，由于臭名昭著的聚集引起的猝灭（ACQ）效应，合成高固态效率D–A结构化的发射器仍然是一个挑战。尽管据报道某些D–A系统显示出聚集诱导排放（AIE）行为，但大多数系统在高极性溶剂中仅具有选择性AIE活性，与非极性溶剂相比，其固相排放效率降低。在这里，我们报告基于三苯胺（TPA）和2,3,3-三苯基丙烯腈（TPAN）的D–A体系结构，即TPA3TPAN和DTPA4TPAN。用TPAN修饰芳胺会改变其发射行为，从ACQ变为AIE，使所得的TPA3TPAN和DTPA4TPAN在普通溶剂中不发光，但由于其高度扭曲的构型而聚集成纳米颗粒，固体粉末和薄膜时具有高发射性。由于它们的分子内电荷转移（ICT）属性，这两种化合物还显示出红移效应。结合了ICT和AIE功能，使TPA3TPAN和DTPA

  DOI：

  10.1021/cm300416y

文献信息

• Efficient Solid Emitters with Aggregation-Induced Emission and Intramolecular Charge Transfer Characteristics: Molecular Design, Synthesis, Photophysical Behaviors, and OLED Application
  作者：Wang Zhang Yuan、Yongyang Gong、Shuming Chen、Xiao Yuan Shen、Jacky W. Y. Lam、Ping Lu、Yawei Lu、Zhiming Wang、Rongrong Hu、Ni Xie、Hoi Sing Kwok、Yongming Zhang、Jing Zhi Sun、Ben Zhong Tang

  DOI：10.1021/cm300416y

  日期：2012.4.24

  aggregation-induced emission (AIE) behaviors, most are only selectively AIE-active in highly polar solvents, showing decreased solid-sate emission efficiencies compared to those in nonpolar solvents. Here we report the triphenylamine (TPA) and 2,3,3-triphenylacrylonitrile (TPAN) based D–A architectures, namely, TPA3TPAN and DTPA4TPAN. Decoration of arylamines with TPAN changes their emission behaviors from ACQ to AIE

  发射电子供体-受体（DA）共轭物在生物光子学，双光子吸收材料，有机激光器，长波长发射器等方面具有广泛的应用。但是，由于臭名昭著的聚集引起的猝灭（ACQ）效应，合成高固态效率D–A结构化的发射器仍然是一个挑战。尽管据报道某些D–A系统显示出聚集诱导排放（AIE）行为，但大多数系统在高极性溶剂中仅具有选择性AIE活性，与非极性溶剂相比，其固相排放效率降低。在这里，我们报告基于三苯胺（TPA）和2,3,3-三苯基丙烯腈（TPAN）的D–A体系结构，即TPA3TPAN和DTPA4TPAN。用TPAN修饰芳胺会改变其发射行为，从ACQ变为AIE，使所得的TPA3TPAN和DTPA4TPAN在普通溶剂中不发光，但由于其高度扭曲的构型而聚集成纳米颗粒，固体粉末和薄膜时具有高发射性。由于它们的分子内电荷转移（ICT）属性，这两种化合物还显示出红移效应。结合了ICT和AIE功能，使TPA3TPAN和DTPA
• Synthesis of Fluorene-Bridged Arylene Vinylene Fluorophores: Effects of End-Capping Groups on the Optical Properties, Aggregation Induced Emission
  作者：Guo-Feng Zhang、Tao Chen、Ze-Qiang Chen、Matthew P. Aldred、Xianggao Meng、Ming-Qiang Zhu

  DOI：10.1002/cjoc.201500240

  日期：2015.8

  We have synthesized a series of fluorene‐based fluorophores, in which a central fluorene core has been modified with different peripheral arylene vinylene substituents that are able to activate aggregation‐induced emission (AIE) characteristics. 9,9‐Dioctylfluorene doubly end‐capped at the 2,7‐positions with triphenylethene groups, such as 4‐(2,2‐diphenylvinyl)phenyl (F1‐(2,2)‐HTPE) and 4‐(1,2‐diphenylvinyl)phenyl

  我们合成了一系列基于芴的荧光团，其中中心芴核已被不同的周边亚芳基亚乙烯基取代基修饰，从而能够激活聚集诱导发射（AIE）特性。9,9-二辛基芴在2,7-位双封端，带有三苯基乙烯基团，例如4-（2,2-二苯基乙烯基）苯基（F1-（2,2）-HTPE）和4-（1,2合成了-二苯基乙烯基）苯基（F1-（1,2）-HTPE），并与四苯基乙烯类似物（F1-TPE）进行了比较。两个（2,2）-HTPE和F1-（1,2）-HTPE辉光带与发射最大值THF溶液深蓝色荧光（F1- λ EM 426和403纳米），分别。该λ EMF1-（2,2）-HTPE固态固态红移至458 nm，F1-（1,2）-HTPE固态固态红移至437 nm。荧光量子产率（ø ˚F）的（2,2）-HTPE（F1- ø ˚F = 35.1％）和F1-（1,2）-HTPE（ø ˚F = 26.2％）被发现在溶液中要高的比较到F1-TPE的近猝灭（ø
• Optical properties and red to near infrared piezo-responsive fluorescence of a tetraphenylethene–perylenebisimide–tetraphenylethene triad
  作者：Matthew P. Aldred、Guo-Feng Zhang、Chong Li、Gui Chen、Tao Chen、Ming-Qiang Zhu

  DOI：10.1039/c3tc31452a

  日期：——

  The optical properties and piezofluorochromic behaviour of N,N′-dioctyl-1,7-di(4-(1,2,2-triphenyl)vinyl)phenyl-3,4:9,10-tetracarboxylic perylenebisimide (PBI–TPE) have been investigated. PBI–TPE shows strong fluorescence in non-polar solvents, in contrast to complete quenching in common moderately polar to polar solvents, most likely due to intramolecular charge transfer (ICT) from the donating tetraphenylethene (TPE) groups to the acceptor perylenebisimide core. The solid-state fluorescence is morphology dependent, in which the amorphous-state displays near infra-red emission at 744 nm and the crystalline state shows a blue-shift in emission at 665 nm with a difference of 79 nm. Crystalline PBI–TPE exhibits stress induced amorphisation resulting in a piezo-responsive behaviour in which the metastable amorphous state and crystalline state can be interconverted by grinding and thermal annealing (200 °C)/recrystallisation. This reciprocal conversion gives rise to the piezofluorochromic effect. Finally, crystalline microstructures were used to fabricate a microwire field-effect transistor (MFET) with the effective mobility (μe) and capacitance (Ci) estimated to be 3.11 × 10−5 cm2 V−1 s−1 and 1.51 × 10−15 F, respectively.

  N,N'-二辛基-1,7-二(4-(1,2,2-三苯基)乙烯)苯-3,4:9,10-四羧酸酰基苯并咪唑 (PBI–TPE) 的光学性质和压电荧光变色行为已被研究。PBI–TPE 在非极性溶剂中表现出强荧光，而在常见的中等极性到极性溶剂中则完全淬灭，这最可能是由于供体四苯乙烯 (TPE) 基团向受体苔藓双咪唑核心的分子内电荷转移 (ICT)。固态荧光依赖于形态，其中无定形态在744 nm处显示近红外发射，而晶态在665 nm处的发射则出现蓝移，差异为79 nm。晶态PBI–TPE表现出应力诱导的无定形化，从而导致压电响应行为，其中亚稳无定形态和晶态可以通过磨碎和热退火（200°C）/再结晶互相转化。这种相互转化产生了压电荧光变色效应。最后，晶态微结构被用于制造微线场效应晶体管 (MFET)，其有效迁移率 (μe) 和电容 (Ci) 分别估计为 3.11 × 10⁻⁵ cm² V⁻¹ s⁻¹ 和 1.51 × 10⁻¹⁵ F。
• Aggregation induced emission and mechanochromism in pyrenoimidazoles
  作者：Thaksen Jadhav、Bhausaheb Dhokale、Shaikh M. Mobin、Rajneesh Misra

  DOI：10.1039/c5tc02181b

  日期：——

  Pyrene-based solid state emitters 3a and 3b were designed and synthesized by the Pd-catalyzed Suzuki cross-coupling reaction. Pyrenoimidazoles 3a and 3b exhibit strong AIE and reversible mechanochromic behavior with color contrast between blue and green.

  基于芘的固态发光体3a和3b是通过Pd催化的Suzuki交叉偶联反应设计和合成的。Pyrenoimidazoles 3a和3b表现出强的聚集诱导发光效应和可逆的机械致色行为，其颜色在蓝色和绿色之间有明显的对比度。
• Multifunctional pyrenoimidazole substituted tetraphenylethylene derivatives: Mechanochromism and aggregation-induced emission
  作者：Venugopal Thanikachalam、Uthirapathy Karunakaran、Jayaraman Jayabharathi、Shanmugam Thilagavathy

  DOI：10.1016/j.jphotochem.2021.113489

  日期：2021.11

  analyzed. The pyrenoimidazoles, TPE-SPNC and TPA-SPNC show strong aggregation induced emission (AIE) and reversible mechanochromic behavior. In the aggregated state, the restricted intramolecular rotation (RIR) of phenyl rings of TPE (TPE-SPNC) and TPA (TPA-SPNC) are suppressed which reduced the non-radiative excited state energy loss leading increase of fluorescence intensity. The quantum yield of TPE-SPNC/TPA-SPNC

  具有集成了聚集诱导发射 (AIE) 荧光团的螺旋桨形结构的有机分子，即 ( E )-4-(10-(2-(4'-(1,2,2-triphenylvinyl)-[1,1'-biphenyl) ]-4-基）乙烯基）-9H-芘[4,5-d]咪唑-9-基）-1-萘腈（TPE-SPNC）和（E)-4-(10-(2-(4'-(1-cyano-2,2-diphenylvinyl)-[1,1'-biphenyl]-4-yl)vinyl)-9H-芘[4,5- d]imidazol-9-yl)-1-naphthonitrile (TPA-SPNC) 已经合成并探索了它们的机械氟致变色 (MFC) 特性。分析了 TPE-SPNC 和 TPA-SPNC 的热、电化学和光物理性能。芘咪唑、TPE-SPNC 和 TPA-SPNC 表现出强烈的聚集诱导发射 (AIE) 和可逆的机械变色行为。在聚集状态下，TPE（TPE-