4-dodecyloxy[(trimethylsilyl)ethynyl]benzene | 179925-08-7

• 英文名称: 4-dodecyloxy[(trimethylsilyl)ethynyl]benzene
• 英文别名: 2-(4-dodecoxyphenyl)ethynyl-trimethylsilane
• CAS: 179925-08-7
• 化学式: C₂₃H₃₈OSi
• 分子量: 358.64
• InChiKey: SUSKEMWMORVIRN-UHFFFAOYSA-N

物化性质

• 沸点：
  423.4±37.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.22
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-dodecyloxy[(trimethylsilyl)ethynyl]benzene 在 四(三苯基膦)钯 甲醇 、 copper(l) iodide 、 sodium fluoride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Enhanced Aggregation of Derivatized Tolan Surfactants through Donor−Acceptor Interactions at the Air−Water Interface and in Langmuir−Blodgett Films

  摘要：

  Control of aggregation behavior of derivatized surfactants by moderately polar functional groups as well as the role of charge-transfer interactions governing photophysical phenomena was studied using surfactants incorporating the diphenylacetylene (tolan) chromophore (TFAs) modified with either a sulfone or an ether group (sTA or oTA, respectively). H aggregation is prevalent in these systems as monitored by the spectral shifts of absorption and emission. Packing of surfactants and aggregation were found to be strongly influenced by the presence of bivalent metal cations, Cd2+, in the subphase, as demonstrated by molecular area and chain orientation measurements. The nature of the aggregates formed from sTA surfactants is directly affected by complexation of the acid headgroup; in contrast, the associated oTA chromophore aggregation is unaffected by subphase modifications, despite the altered packing of surfactant chains. The photophysical behavior of aggregated TFAs in monolayer systems was followed at the air-water interface as well as with supported films on quartz, and conclusions can be made of the surfactant arrangements' stability. A unique mixed aggregate was formed when both the ether- and sulfone-derivatized TFAs were incorporated into a single phosphatidylcholine molecule (mixed PC) and deposited as an LB film. This monolayer exhibits additional enhancement in aggregation properties attributed to donor-acceptor interactions between the tolan chromophores that are distinct from a statistically mixed LB sample prepared from a mixture of TFAs. The current results are viewed in terms of general principles governing aggregation for a family of chromophore-derivatized surfactants in LB film.

  DOI：

  10.1021/jp960579g
• 作为产物：
  描述：

  4-溴苯酚 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 、 三苯基膦 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 42.0h， 生成 4-dodecyloxy[(trimethylsilyl)ethynyl]benzene
  参考文献：
  名称：

  Pi-Extended Ethynyl 21,23-Dithiaporphyrins: A Synthesis and Comparative Study of Electrochemical, Optical, and Self-Assembling Properties

  摘要：

  21,23-Dithiaporphyrins were synthesized containing pi-extending ethynyl substituents at the meso positions. These porphyrins displayed highly bathochromic and broadened absorbance profiles spanning 400-900 nm with molar absorptivities ranging from 2500 to 300,000 M-1 cm(-1). Electrochemically, these ethynyl dithiaporphyrins undergo a single oxidation at 0.44 or 0.57 V and reduction at -1.17 or -1.08 V versus a ferrocene/ferrocenium internal standard depending on the type of functionalization appended to the ethynyl group. DFT calculations predict that the delocalization of the frontier molecular orbitals should expand onto the meso positions of the ethynyl 21,23-dithiaporphyrins; shrinking the HOMO-LUMO energy gap by destabilizing the HOMO energy. Indeed, the DFT results agree with our optical and electrochemical assessments. Finally, differential scanning calorimetry combined with cross-polarized optical microscopy and powder X-ray diffraction was used to assess the ability of these porph-yrins for long-range order. For the ethynylphenyl alkoxy 21,23-dithiaporphyin, birefringent, soft-crystalline-like domains were observed by polarized microscopy, which are marginally sustained by a low-level of crystallinity detected in the XRD, suggesting that long-range ordering is possible. Overall, ethynyl 21,23-dithiaporphyrins are able to harvest much lower energy light and possess lower oxidation and reduction potentials compared to their pyrrolic analogues, which are desirable properties for applications in organic electronics.

  DOI：

  10.1021/acs.joc.5b01299

文献信息

• Functionalizable Polycyclic Aromatics through Oxidative Cyclization of Pendant Thiophenes
  作者：John D. Tovar、Aimee Rose、Timothy M. Swager

  DOI：10.1021/ja0262636

  日期：2002.7.1

  arylene-ethynylene polymers with varying degrees of chromophore aromatization and used them to probe the effects of synthetically imposed rigidity on polymer photophysical behavior. The symmetries and effective conjugation pathways within the monomers play a key role in determining photophysical properties. We observed that rigid, aromatized chromophores generally led to increased excited-state lifetimes

  我们提出了通过氯化铁（III）介导的氧化环化从噻吩基前体获得大的含硫多环芳烃的一般策略。通过将噻吩基部分靠近相邻的芳烃，我们将氧化的中间体引导到受控的环化途径中，有效地抑制了聚合物的形成。利用这些环化化合物及其噻吩基前体，我们研究了聚 (2) 等聚合物的环化/聚合途径。这些芳香核内硫原子的 α 位未取代位置允许有效卤化和进一步功能化。作为示范，我们制备了一系列具有不同发色团芳构化程度的亚芳基-乙炔聚合物，并用它们来探索合成施加的刚性对聚合物光物理行为的影响。单体内的对称性和有效的共轭途径在决定光物理性质方面起着关键作用。我们观察到刚性的、芳香化的发色团通常通过降低荧光衰减的辐射率来增加激发态寿命。
• Two-Photon Absorption Properties of Proquinoidal D-A-D and A-D-A Quadrupolar Chromophores
  作者：Kimihiro Susumu、Jonathan A. N. Fisher、Jieru Zheng、David N. Beratan、Arjun G. Yodh、Michael J. Therien

  DOI：10.1021/jp2000738

  日期：2011.6.9

  The BTD- and TDQ-containing structures exhibit blue-shifted two-photon absorption (TPA) spectra relative to their corresponding one-photon absorption (OPA) spectra, and display high TPA cross sections (>100 GM) within these spectral windows. D-A-D and A-D-A structures that feature more extensive conjugation within this series of compounds exhibit larger TPA cross sections consistent with computational

  我们报告了一系列具有原醌型 π 芳族受体的四极分子的合成、单光子和双光子吸收光谱、荧光和电化学特性。这些四极分子具有供体-受体-供体 (DAD) 或受体-供体-受体 (ADA) 电子基序，并具有4- N , N-二己基氨基苯基、4-十二烷氧基苯基、4-( N , N-二己基氨基)苯并[ c ][1,2,5] 噻二唑基或 2,5-二辛氧基苯基电子供体部分和苯并[ c ][1,2,5] 噻二唑 (BTD) 或 6,7-双 (3',7'-二甲基辛基) [1,2,5]噻二唑并[3,4- g]喹喔啉 (TDQ) 电子受体单元。这些共轭结构在非极性溶剂中具有高发射率，并且相对于包含亚苯基组分代替 BTD 和 TDQ 部分的类似参考化合物，它们各自的最低能量吸收带显示出较大的光谱红移。基于 BTD 的 DAD 和 ADA 发色团表现出增加的荧光发射红移，并伴随着荧光量子产率 (Φ f) 随着溶剂极性的增
• Enhanced anhydrous proton conduction in binary mixtures of 1H-imidazole–1H-1,2,3-triazole based compounds
  作者：Dipankar Basak、Craig Versek、Jacob A. Harvey、Scott Christensen、Jibben Hillen、Scott M. Auerbach、Mark T. Tuominen、D. Venkataraman

  DOI：10.1039/c2jm32835f

  日期：——

  What is the impact of mixing two proton-conducting heterocycles on proton conductivity? Herein we answer this question through our investigations on two linear rod-like compounds 2-(4-(dodecyloxy)phenyl)-1H-imidazole (4) and 5-(4-(dodecyloxy)phenyl)-1H-1,2,3-triazole (10). We have found that mixtures of molecules 4 and 10 at certain compositions show enhanced proton conductivity compared to their pure components. We attribute the increased conductivity in these materials to the increased charge density due to facile co-ionization and increased mobility due to the incorporation of long alkyl chains, which prevent crystallization of protogenic groups while maintaining the required hydrogen bonded network. Our results suggest a new strategy for enhancing intrinsic proton conductivity in heterocyclic systems.

  混合两种质子导电杂环对质子导电性的影响是什么？在这里，我们通过对两种线性棒状化合物2-(4-(十二烷氧)苯基)-1H-咪唑 (4) 和 5-(4-(十二烷氧)苯基)-1H-1,2,3-三唑 (10) 的研究来回答这个问题。我们发现，在某些成分比例下，混合物4和10的质子导电性相比于它们的纯组分有了增强。我们将这些材料中导电性增强归因于因容易共离子化而导致的电荷密度增加以及由于长烷基链的引入而导致的迁移性增强，这些长烷基链防止了质子化基团的晶化，同时维持了所需的氢键网络。我们的结果为增强杂环系统中固有的质子导电性提供了一种新策略。
• NOVEL CONJUGATED MATERIALS FEATURING PROQUINOIDAL UNITS
  申请人：Therien Michael J.

  公开号：US20090221762A1

  公开（公告）日：2009-09-03

  The invention concerns compounds, oligomers, and polymers that contain: (I), (II), (III), or (IV) groups; where “-” indicates points of attachment.

  该发明涉及含有(I)、(II)、(III)或(IV)基团的化合物、寡聚体和聚合物；其中“-”表示附着点。
• Conjugated materials featuring proquinoidal units
  申请人：The Trustees Of The University Of Pennsylvania

  公开号：US07842758B2

  公开（公告）日：2010-11-30

  The invention concerns compounds, oligomers, and polymers that contain: (I), (II), (III), or (IV) groups; where “-” indicates points of attachment.

  该发明涉及包含(I)、(II)、(III)或(IV)基团的化合物、寡聚物和聚合物；其中“-”表示连接点。