9,10-bis(trimethylsilyloxy)anthracene | 28871-52-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-bis(trimethylsilyloxy)anthracene
• 英文别名: 9,10-Disiloxyanthracen；Silane, [9,10-anthracenediylbis(oxy)]bis[trimethyl-；trimethyl-(10-trimethylsilyloxyanthracen-9-yl)oxysilane
• CAS: 28871-52-5
• 化学式: C₂₀H₂₆O₂Si₂
• 分子量: 354.596
• InChiKey: ZUTHBPDFOVRVSZ-UHFFFAOYSA-N

物化性质

• 熔点：
  132 °C
• 沸点：
  403.9±18.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9,10-bis(trimethylsilyloxy)anthracene 在 lithium perchlorate 作用下， 以 乙腈 为溶剂， 以92%的产率得到蒽醌
  参考文献：
  名称：

  Oxidation of hydroquinone silyl ethers to quinones

  摘要：

  DOI：

  10.1021/ja00535a030
• 作为产物：
  描述：

  蒽醌 以96 g的产率得到9,10-bis(trimethylsilyloxy)anthracene
  参考文献：
  名称：

  Synthesis of new macrocylic polyoxa [X,X] and [X] (9,10)-anthracenophanes from 9,10-bistrimethylsiloxyanthracene

  摘要：

  DOI：

  10.1016/s0040-4039(00)88400-2

文献信息

• Synthesen mit verbindungen R3MHgMR3 und (R2MHg)n (MC, Si, Ge, Sn)
  作者：Guido Neumann、Wilhelm P. Neumann

  DOI：10.1016/s0022-328x(00)90077-9

  日期：1972.9

  Aromatic aldehydes are reductively dimerised by Me3SiHgSiMe3 (I), yielding bis(O-silyl)hydrobenzoin derivatives. 1,2-Diketones undergo 1,4-addition with formation of bis(O-silyl)enediols, while esters of conjugated dicarboxylic acids give O-silyl ketene acetals: maleic yields mainly the C,O-bissilyl derivative (1,4-addition), whereas fumaric and ethylene tetracarboxylic esters yield mainly the corresponding

  芳香醛是由我还原二聚3 SiHgSiMe 3（I），得到双（ø -甲硅烷基）氢化苯偶姻衍生物。1,2-二酮经过1,4-加成反应生成双（O-甲硅烷基）烯二醇，而共轭二羧酸的酯则生成O-甲硅烷基烯酮缩醛：马来酸主要产生C，O-双甲硅烷基衍生物（1,4- ，而富马酸酯和乙烯四羧酸酯主要产生相应的O，O-双甲硅烷基产物（1,6-加成）。1,2-和1,4-醌很容易被（I）转化成相应的双O-甲硅烷基）苯系。
• The Synthesis and Spectroscopic Properties of a [2]Catenane Incorporating an Anthracene Chromophoric Unit
  作者：R. Ballardini、V. Balzani、A. Credi、M. T. Gandolfi、D. Marquis、L. Pérez-García、J. F. Stoddart

  DOI：10.1002/(sici)1099-0690(199801)1998:1<81::aid-ejoc81>3.0.co;2-p

  日期：1998.1

  absorption spectrum of the [2]catenane is noticeably different from the sum of the spectra of its two cyclic components, particularly as far as the presence of a very broad charge-transfer (CT) band in the visible spectral region (λmax = 545 nm, ϵmax = 615 M−1 cm−1) is concerned.Comparison with the CT band of a model compound shows that the very broad CT band of the [2]catenane is in fact the result of

  一种改性的双对亚苯基-34-冠-10 环，其中一个 1,4-二氧苯单元已被 9,10-二氧蒽单元取代，已被用作形成环双（百草枯）的模板。对亚苯基）。1H NMR 光谱表明产生的 [2] 链烯仅以平移异构形式存在于溶液中，其中 (a) 只有 1,4-二氧基苯环占据四阳离子环芳的中心腔，(b)大的 9,10-二氧蒽单元阻止了冠醚环通过环芳环旋转。研究了这种新的 [2] 链烯及其游离态冠醚组分的吸收光谱和发光特性，并与 1,4-二甲氧基苯和模型蒽衍生物的吸收光谱和发光特性进行了比较，在蒽环的 9 和 10 位上带有甲基化的三甘醇链。虽然冠醚的吸收光谱是两个组分发色团部分光谱的总和，但其发射光谱仅显示 9,10-二氧蒽型单元的荧光带。激发光谱表明，冠醚中 1,4-二氧基苯型发射的消失是由于从 1,4-二氧基苯到 9 ,10-二氧蒽类单元。[2] 链烯的吸收光谱与其两个环状组分的光谱总和明显不同，尤其是在可见光谱区域
• Smart emissive hybrid dynamer and nanocomposite made of complementary organic and inorganic emitters combined via a supramolecular Janus synthon
  作者：Ilya V. Kashnik、Jeanne Rebours、Noée Dumait、Konstantin A. Brylev、Yann Molard

  DOI：10.1039/d4tc01043d

  日期：——

  blue-emitting anthracene derivatives bearing one or two thymine moieties, respectively, are associated via hydrogen bonds to a red-emitting [Mo6I8(OCOC2F5)6]2− anion, whose charge is counter-balanced by a Janus-type organic synthon made of an imidazolium head bearing an organic chain terminated with a complementary diamidopyridine group. The generated supramolecular hydrogen-bonded complex and dynamers

  分别带有一个或两个胸腺嘧啶部分的单位和二位发蓝光蒽衍生物通过氢键与发红光的 [Mo 6 I 8 (OCOC 2 ) 6 ] 2− 阴离子，其电荷通过由带有有机基团的咪唑头部制成的 Janus 型有机合成子来平衡链以互补的二氨基吡啶基团封端。生成的超分子氢键配合物和动力剂在溶液中显示蓝色发射，在固态中显示红色发射。一旦嵌入 PMMA 薄膜中，发电机发射颜色就由 UV-2A 区域的照射时间和功率控制。这种动态发光行为允许在薄膜上进行短暂的光学书写。
• Photoresponsive Supramolecular Systems: Synthesis and Photophysical and Photochemical Study of Bis-(9,10-anthracenediyl)coronands AAOnOn
  作者：Damien Marquis、Jean-Pierre Desvergne、Henri Bouas-Laurent

  DOI：10.1021/jo00129a045

  日期：1995.12

  Monocyclic bis-(9,10-anthracenediyl)coronands denoted AAO(n)O(n) (A = (9,10-anthracenediyl, n. indicating the number of ethyleneoxy repeating units between two aromatic rings) were designed as photoresponsive systems. Their synthesis is described; their spectroscopic properties were found to be in agreement with the X-ray structures. Special attention was devoted to AAO(5)O(5), which gives coronates with Na+ and K+. It was observed that one molecule of AAO(5)O(5), displays a positive cooperative effect in binding two sodium cations, in contrast with previous reports on bicyclic coronands. Moreover, in acetonitrile, this effect, clear in the ground state (K-11 = 180 M(-1), K-12 240 M(-1)) was found to be stronger in the excited state (K-11 = 200 M(-1), K-12 = 500 M(-1)). With K+, AAO(5)O(5), generates a 1:1 complex (K approximate to 9 M(-1) in methanol). Spectroscopic properties were shown to be triggered by cation concentration, specifically the fluorescence emission which undergoes an important intensity and wavelength redistribution in favor of the excimer: the maximum wavelength is shifted from 530 nm (free Ligand) to 570 nn (sodium biscoronate), i.e., Delta nu ca. 1350 cm(-1) and the excimer intensity is multiplied by ca. 3. The photocyclomerization (intramolecular dimerization of the anthracene nucleus) was demonstrated to be regiospecifically directed by Na+; in methanol, the free receptor exclusively generates the 9,10:1',4' photoadduct (phi(R) approximate to 2 x 10(-4)) whereas the sodium biscoronate leads to the classical 9,10:9',10' photoadduct (phi(R) approximate to 8 x 10(-3)). Finally, a transient kinetic analysis versus temperature allowed the determination of the conformational mobility of the free receptor within the nanosecond range; in the singlet excited state it is best described by the sequence M(1)* --> M(2)* --> E where M* stands for the locally excited state and E the excimer state species. At room temperature, in methanol, excimer lifetimes were found to be as follows: free Ligand, 23 ns; sodium biscoronate, 165 ns; and potassium monocoronate, 215 ns.
• Highly Efficient and Chemoselective Reductive Bis-silylation of Quinones by Silyltellurides
  作者：Shigeru Yamago、Hiroshi Miyazoe、Kazunori Iida、Jun-ichi Yoshida

  DOI：10.1021/ol006581e

  日期：2000.11.1

  [GRAPHICS]Silyltellurides serve as new silicon-based chemoselective reducing agents and reduce quinones to the corresponding bis-silylated hydroquinones. The reaction proceeds under ambient thermal conditions without the need of any additional promoters or catalysts and gives the products in excellent yields. Several control experiments suggest that the reaction is initiated by a single electron transfer from silyltellurides to quinones.