2,3,4,5,7,8,9,10-octafluorophenazine | 18232-24-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,3,4,5,7,8,9,10-octafluorophenazine
• 英文别名: octafluorophenazine；perfluorophenazine；octafluoro-phenazine；Phenazine, octafluoro-；1,2,3,4,6,7,8,9-octafluorophenazine
• CAS: 18232-24-1
• 化学式: C₁₂F₈N₂
• 分子量: 324.133
• InChiKey: XZTHSCZJCCIPGU-UHFFFAOYSA-N

物化性质

• 熔点：
  234 °C
• 沸点：
  365.1±37.0 °C(Predicted)
• 密度：
  1.823±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  10

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2,3,4,5,7,8,9,10-octafluorophenazine 在 氨 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以88%的产率得到2-aminoperfluorophenazine
  参考文献：
  名称：

  Red solid-state fluorescent aminoperfluorophenazines

  摘要：

  The solid-state fluorescence of 2-amino-, 2-ethylamino, 2-diethylamino-, and 2.7-bis(diethylamino)perfluorophenazines was examined. They showed their fluorescence maxima in the range of 584-637 nm. The solid-state fluorescence quantum yield of 2-diethylamino derivative was highest among these derivatives, there being 0.22. X-ray crystallographic analysis suggests that the 2-diethylamino derivative has no strong intermolecular interactions among adjacent molecules to show intense fluorescence, whereas the other derivatives have network NH/F hydrogen, pi-pi, and CH/F interactions to reduce solid-state fluorescence intensity. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2009.06.095
• 作为产物：
  描述：

  N-pentafluorophenyl-3,4,5,6-tetrafluorophenylene-1,2-diamine 在 sodium hydride 作用下， 以 乙醚 为溶剂， 以0%的产率得到2,3,4,5,7,8,9,10-octafluorophenazine
  参考文献：
  名称：

  多氟芳族胺的电化学氧化—Ⅰ：氟吩嗪的合成

  摘要：

  通过在铂阳极上对五氟苯胺进行电化学氧化，可获得八氟吩嗪和十氟偶氮苯。类似地，octafluorophenazine 2 ħ -heptafluorophenazine和1,2,3,4- tetrafluorophenazine已经从获得的2- aminononafluorodiphenylamine，2-氨基-4' ħ -octafluorodiphenylamine和2-氨基-2'，3,4,5,6-五氟二苯胺。还描述了2-硝基-和2-氨基-多氟二苯胺的合成。

  DOI：

  10.1016/s0040-4020(01)92956-4

文献信息

• Chemical oxidation of fluoroanilines to fluoroazobenzenes and fluorophenazines with potassium ferricyanide and potassium hydroxide
  作者：Elisa Leyva、Concepción Medina、Edgar Moctezuma、Socorro Leyva

  DOI：10.1139/v04-150

  日期：2004.12.1

  The oxidation of several fluoroanilines with potassium ferricyanide and potassium hydroxide is described. In this oxidation, the major products are fluoroazobenzenes. In the case of 2-fluoro-substituted anilines, heterocyclic fluorophenazines were obtained in low to moderate yields. The optimal conditions for the reaction and the mechanism are presented.Key words: oxidation, fluoroanilines, fluoroazobenzenes

  描述了用铁氰化钾和氢氧化钾氧化几种氟苯胺。在该氧化中，主要产物是氟偶氮苯。在 2-氟取代苯胺的情况下，杂环氟吩嗪以低到中等的产率获得。给出了反应的最佳条件和反应机理。关键词：氧化，氟苯胺，氟偶氮苯，氟吩嗪。
• Oxidation of fluoroanilines to fluoroazobenzenes with potassium ferricyanide and KOH
  作者：Elisa Leyva、Elena Monreal、Concepción Medina、Socorro Leyva

  DOI：10.1016/s0040-4039(97)10131-9

  日期：1997.11

  The oxidation of several fluoroanilines to fluoroazobenzenes with potassium ferricyanide and KOH in a solvent mixture of is described.

  描述了在铁溶剂中用铁氰化钾和KOH将几种氟苯胺氧化为氟偶氮苯。
• Reaction, identification, and fluorescence of aminoperfluorophenazines
  作者：Masaki Matsui、Masayuki Suzuki、Izumi Nunome、Yasuhiro Kubota、Kazumasa Funabiki、Motoo Shiro、Shinya Matsumoto、Hisayoshi Shiozaki

  DOI：10.1016/j.tet.2008.06.079

  日期：2008.9

  dialkyl-, and arylamines to afford the corresponding 2-amino-substituted derivatives. 2-(Ethylamino)- and 2-(diethylamino)perfluorophenazine reacted with another molar amount of ethylamine and diethylamine to preferentially provide the 2,7-disubstituted derivatives, respectively. Perfluoro(2,7-dimethylphenazine) was allowed to react with ethylamine to give the 1-ethylamino derivative. These regiospecific

  全氟吩嗪区域特异性地与单烷基，二烷基和芳基胺反应，得到相应的2-氨基取代的衍生物。2-（乙基氨基）-和2-（二乙基氨基）全氟吩嗪与另一摩尔量的乙胺和二乙胺反应，分别分别优选提供2,7-二取代的衍生物。使全氟（2，7-二甲基吩嗪）与乙胺反应，得到1-乙基氨基衍生物。这些区域特异性反应通过密度泛函理论（DFT）计算得到解释。全氟吩嗪与乙二胺反应生​​成2,3环化的N，N'-双（2-全氟吩嗪基）衍生物。这些氨基取代的产品表现出紫外可见吸收（最大λ）和在己烷中分别在439–536和524–613 nm范围内的荧光最大值（F max）。它们中的一些表现出强烈的荧光。
• Effects of the alkyl group in (dialkylamino)perfluorophenazines on the melting point and fluorescence properties
  作者：Siddanagouda Biradar、Yasuhiro Shigemitsu、Yasuhiro Kubota、Kazumasa Funabiki、Hiroyasu Sato、Masaki Matsui

  DOI：10.1039/c4ra09342a

  日期：——

  The alkyl groups in 2-(dialkylamino)- and 2,7-bis(dialkylamino)perfluorophenazines drastically affected the melting point and solid-state fluorescence. 2-(Dialkylamino)- and 2,7-bis(dialkylamino) derivatives such as 2-(dioctylamino)-, 2-(didodecylamino)-, and 2,7-bis(dioctylamino)perfluorophenazines were liquid at ambient temperature, whereas shorter and longer dialkylamino derivatives were solid. 2-(Dioctadecylamino)perfluorophenazine exhibited a fluorescence maximum at 581 nm, being significantly blue-shifted compared with the other derivatives, with the most intense fluorescence quantum yield of 0.29 in the crystalline form. This result is attributed to the isolated dimer-type packing coming from long octadecyl groups. 2-(Dimethylamino)perfluorophenazine showed positive fluorescence solvatochromism due to a large dipole moment in the excited state. The computational analysis of (2-(dimethylamino)perfluorophenazine suggests that the red-shift of the fluorescence maximum in the crystalline form, compared with that in solution, mainly comes from π–π interactions with adjacent molecules. The fluorescence lifetime of 2-(dioctadecylamino)perfluorophenazine was significantly longer compared with 2-(dioctadecylamino)phenazine owing to the aromatic C–F bonds.

  2-（二烷基氨基）- 和 2,7-双（二烷基氨基）全氟吩嗪中的烷基对熔点和固态荧光有很大影响。2-(二烷基氨基)-和 2,7-双(二烷基氨基)衍生物，如 2-(二辛基氨基)-、2-(十二烷基氨基)-和 2,7-双(二辛基氨基)全氟吩嗪在环境温度下呈液态，而较短和较长的二烷基氨基衍生物则呈固态。2-(双十八烷基氨基)全氟吩嗪在 581 纳米波长处显示出荧光最大值，与其他衍生物相比明显偏蓝，结晶形式的荧光量子产率最高，为 0.29。这一结果归因于长十八烷基产生的孤立二聚体型堆积。由于激发态的偶极矩较大，2-（二甲基氨基）全氟吩嗪显示出正的荧光溶解色度。对（2-（二甲基氨基）全氟吩嗪）的计算分析表明，与溶液中的荧光最大值相比，晶体中的荧光最大值的红移主要来自与相邻分子的π-π相互作用。与 2-(双十八烷基氨基)吩嗪相比，2-(双十八烷基氨基)全氟吩嗪的荧光寿命明显更长，这是由于芳香族 C-F 键的缘故。
• Visible light induced photo-oxidation of water. Formation of intermediary hydroxyl radicals through the photoexcited triplet state of perfluorophenazine
  作者：Takayuki Kitamura、Hiroyuki Fudemoto、Yuji Wada、Kei Murakoshi、Mitsuhiro Kusaba、Nobuaki Nakashima、Tetsuro Majima、Shozo Yanagida

  DOI：10.1039/a604920f

  日期：——

  1,2,3,4,5,6,7,8-Octafluorophenazine (F-Phen) has an absorption spectrum in the longer wavelength extending to the visible-light region and has a more positive oxidation potential than for unfluorinated phenazine. F-Phen has been photolysed with water in acetonitrile under visible-light irradiation to produce stoichiometrically 1,3,4,5,6,7,8-heptafluoro-2-hydroxyphenazine (F-Phen-2-OH). Photolysis of F-Phen with water in the presence of benzene leads to the formation of phenol followed by the disappearance of F-Phen. EPR analysis and laser flash photolysis reveal that the photoexcited triplet state of F-Phen participates in water oxidation to hydroxyl radicals with concurrent conversion to F-Phen-2-OH. The mechanism is discussed with the results of semi-empirical molecular orbital calculations.

  1,2,3,4,5,6,7,8-八氟吩嗪（F-Phen）的吸收光谱波长较长，可延伸至可见光区域，与未氟化的吩嗪相比，其氧化电位更正。在可见光的照射下，F-Phen 与乙腈中的水发生光解反应，按比例生成 1,3,4,5,6,7,8-七氟-2-羟基吩嗪（F-Phen-2-OH）。在苯的存在下，F-Phen 与水发生光解，生成苯酚，随后 F-Phen 消失。EPR 分析和激光闪烁光解显示，F-Phen 的光激发三重态参与了水氧化成羟自由基的过程，并同时转化成 F-Phen-2-OH。该机制与半经验分子轨道计算的结果进行了讨论。