1,8-diiodopyrene | 94142-98-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1,8-diiodopyrene
• CAS: 94142-98-0
• 化学式: C₁₆H₈I₂
• 分子量: 454.049
• InChiKey: JGDDJNOMJSQMOK-UHFFFAOYSA-N

物化性质

• 熔点：
  246-247 °C
• 沸点：
  507.5±23.0 °C(Predicted)
• 密度：
  2.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (4-(tert-butyl)-2-methoxyphenyl)boronic acid 、 1,8-diiodopyrene 在 四(三苯基膦)钯 、 三溴化硼 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成
  参考文献：
  名称：

  O掺杂的纳米石墨烯：通往半导体阳离子混合价络合物的Pyrano / Pyrylium途径。

  摘要：

  在本文中，我们报道了一种有效的合成方法，以制备由π延伸的of衍生的O掺杂的纳米石墨烯。所述衍生物具有高荧光性并且具有低氧化电位。使用电氧化，可以生长阳离子混合价（MV）配合物的晶体，其中有机盐组织成面对面的π堆栈，这是有机电子产品的良好固态排列。可变温度电子顺磁共振（EPR）的测量和弛豫研究表明，沿柱状π堆叠结构的纵轴有很强的电子离域作用。MV盐单晶的电学测量显示出半导体行为，在室温下具有极高的电导率。

  DOI：

  10.1002/anie.201914025
• 作为产物：
  描述：

  1-hydropyrenyl 在 potassium iodate 、 硫酸 、 碘 、 溶剂黄146 作用下， 以 水 为溶剂， 以13%的产率得到1,8-diiodopyrene
  参考文献：
  名称：

  O掺杂的纳米石墨烯：通往半导体阳离子混合价络合物的Pyrano / Pyrylium途径。

  摘要：

  在本文中，我们报道了一种有效的合成方法，以制备由π延伸的of衍生的O掺杂的纳米石墨烯。所述衍生物具有高荧光性并且具有低氧化电位。使用电氧化，可以生长阳离子混合价（MV）配合物的晶体，其中有机盐组织成面对面的π堆栈，这是有机电子产品的良好固态排列。可变温度电子顺磁共振（EPR）的测量和弛豫研究表明，沿柱状π堆叠结构的纵轴有很强的电子离域作用。MV盐单晶的电学测量显示出半导体行为，在室温下具有极高的电导率。

  DOI：

  10.1002/anie.201914025

文献信息

• Synthesis and Photophysical Properties of a Highly Fluorescent Ditopic Ligand Based on 1,6-Bis(ethynyl)pyrene as Central Aromatic Core
  作者：Stéphanie Leroy-Lhez、Frédéric Fages

  DOI：10.1002/ejoc.200500059

  日期：2005.7

  and purification of two regioisomers of a pyrene derivative containing two ethynyl groups―1,6- and 1,8-bis(ethynyl)pyrene―is described. The former compound was used as a building block for the stepwise synthesis of a highly conjugated, ditopic bis(2,2'-bipyridine) ligand (2) containing the pyrene nucleus at the central core. The fluorescence properties of ligand 2 are reported. (© Wiley-VCH Verlag GmbH

  描述了一种简单的合成路线，用于有效制备和纯化含有两个乙炔基的芘衍生物的两种区域异构体——1,6- 和 1,8-双（乙炔基）芘——。前一种化合物被用作逐步合成高度共轭的双位双 (2,2'-联吡啶) 配体 (2) 的构件 (2)，在中心核心含有芘核。报道了配体2的荧光特性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Chromium Complexes Containing Polycyclic Condensed Aromatic Ligands: Mono‐ and Bidirectional Synthesis from Chromium–Carbenes, Molecular Structures, and Rearrangement Reactions
  作者：Peter Hegele、Gregor Schnakenburg、Jörg Daniels、Karl Heinz Dötz

  DOI：10.1002/ejic.201301409

  日期：2014.3

  Chromium–pyrenylcarbenes accessible from halopyrene precursors undergo benzannulation upon gentle warming with 3-hexyne to give hydroquinoid benzopyrene–Cr(CO)3 complexes. Kinetic benzannulation product 3 rearranges into thermodynamic haptotropomer 4 at 70 °C in octafluorotoluene under first-order kinetics. Further complexation of 3 by Cr(NH3)3(CO)3 affords syn and anti dinuclear chromium–benzopyrene complexes

  可从卤代芘前体获得的铬-芘卡宾在用 3-己炔温和加热后发生苯并环化，得到氢醌苯并芘-Cr(CO)3 配合物。动力学苯并环化产物 3 在 70 °C 下在八氟甲苯中以一级动力学重排成热力学触变体 4。3 与 Cr(NH3)3(CO)3 的进一步络合得到顺式和反双核铬-苯并芘配合物。benzannulation 协议的双向扩展导致形成顺式和反二苯并芘-二铬配合物，其结构特征通过 X 射线分析。
• Tuning the Intramolecular Charge Transfer of Alkynylpyrenes: Effect on Photophysical Properties and Its Application in Design of OFF−ON Fluorescent Thiol Probes
  作者：Shaomin Ji、Jun Yang、Qing Yang、Shasha Liu、Maodu Chen、Jianzhang Zhao

  DOI：10.1021/jo900588e

  日期：2009.7.3

  Green and yellow-emitting 1,6- and 1,8-bis(phenylethynyl) pyrenes (dyes 7, 8, 9, and 10) with different intramolecular charge transfer (ICT) feature were synthesized and the effect of ICT oil the photophysical properties of these derivatives were studied by UV-vis absorption spectra, fluorescence emission spectra, and DFT/TDDFT calculations. For the dyes with electron-pushing group (e.g., -dimethylamino, dye 8 and dye 10), structureless and solvent polarity-sensitive fluorescence emission spectra were observed. Conversely, dye with electron-withdrawing group (e.g., -CN, dye 7) shows structured and solvent polarity-independent emission spectra. OFF-ON fluorescent thiol probes 11 and 12 with 2,4-dinitrobenzenesulfonyl protected ethynylpyrene fluorophore were designed based oil DFT/TDDFT calculations, which predicts dark state (S-1) for these thiol probes (e.g.. oscillator strength f = 0.0086 for S-1 <- S-0 transition of die probe 11). This dark state is induced by the ICT effect with ethynylated pyrene fluorophore as electron donor and 2,4-dinitrobenzenesulfonyl unit as electron acceptor. Cleavage of the 2,4-dinitrobenzenesulfonyl unit by thiol releases the free fluorophore, for which the lowest-lying excited state S, is no longer a dark state, but an emissive state (f = 0.9776 for S-1 <- S-0 transition). These theoretical predictions on die photophysical properties of the molecular probes were fully proved by experimental results. Our results demonstrated that the fluorescence OFF-ON switching of this kind of thiol probe is due to the termination of the ICT effect (which quenches the emission, by a dark S, state) by cleavage of the 2,4-dinitrobenzenesulfonyl unit (as acceptor of ICT effect) with thiols, not the re-establishment of the D-pi-A feature of the fluorophore. These investigation on the pyrene derived green-emitting fluorophores and the DFT/TDDFT calculation aided probe design Suggest that future application of these results may prove useful toward the rational design of fluorophores or fluorescent probes with predetermined photophysical properties.
• Synthesis and property studies of linear and kinked poly(pyreneethynylene)s
  作者：Jhinuk Gupta、Sajini Vadukumpully、Suresh Valiyaveettil

  DOI：10.1016/j.polymer.2010.09.012

  日期：2010.10

  A series of fluorescent conjugated polymers, poly(pyreneethynylene)s, have been designed and synthesized to investigate the effect of shape of polymer backbone on physical properties. Polymers with linear and kinked backbone were synthesized using 1,6- and 1,8-disubstituted pyrene. The target copolymers were designed to incorporate various spacer units, such as, alkoxyphenyl, carbazole and fluorene on the polymer backbone. Characterization of the target compounds was achieved by NMR, IR, GPC and MALDI-TOF mass spectrometry. Detailed investigation on their optical, electrochemical and thermal properties revealed significant contribution of the geometry of polymer backbone towards physical properties. Kinked backbone of cisoid-polymers was found to result in lower optical band gap, less negative E-HOMO and higher thermal stability as compared to their linear analogues, most probably due to the coiling of polymer chains. Comparison of the physical properties of the polymers with those of the model compounds suggested similar extent of conjugation through 1,6- and 1,8-position of pyrene. (C) 2010 Elsevier Ltd. All rights reserved.
• Chaikovskii, V. K.; Novikov, A. N., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 7, p. 1350 - 1352
  作者：Chaikovskii, V. K.、Novikov, A. N.

  DOI：——

  日期：——