3,6-diiodo-1,2-phenylenediamine | 144793-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,6-diiodo-1,2-phenylenediamine
• 英文别名: 3,6-Diiodobenzene-1,2-diamine
• CAS: 144793-03-3
• 化学式: C₆H₆I₂N₂
• 分子量: 359.936
• InChiKey: XKLFKWVSJVIKMW-UHFFFAOYSA-N

物化性质

• 沸点：
  385.9±42.0 °C(Predicted)
• 密度：
  2.605±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6-diiodo-1,2-phenylenediamine 在 bis-triphenylphosphine-palladium(II) chloride 盐酸 、 sodium hydride 、 lead dioxide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙腈 、 苯 为溶剂， 反应 52.33h， 生成
  参考文献：
  名称：

  Single-component organic conductors based on neutral radicals containing the pyrazino-TCNQ skeleton

  摘要：

  Pyrazino-TCNQ (1a) prepared from 5,8-diiodoquinoxaline (4a) is, like TCNQ itself, a strong electron acceptor and gives a stable anion radical salt as well as highly conductive charge-transfer crystals with donors. Substituted derivatives 1b-i were similarly prepared from 3,6-diiodo-1,2-phenylenediamine (5) as a common intermediate, and bulky substituents such as the phenyl or pyridyl groups have very little effect on either the redox properties or planar geometry of la. Neutral radicals 3d-g derived from pyridyl-substituted derivatives 1d-g, respectively, are open-shell donor-pi-acceptor systems with high electrical amphotericity designed as a new motif for single-component organic conductors. The powder conductivity of 3f was as high as 3.2 X 10(-5) S cm-1.

  DOI：

  10.1021/jo00051a015
• 作为产物：
  描述：

  3,6-二溴-1,2-苯二胺 在 盐酸 、 copper(l) iodide 、 selenium(IV) oxide 、 potassium iodide 、 tin(ll) chloride 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 53.5h， 生成 3,6-diiodo-1,2-phenylenediamine
  参考文献：
  名称：

  Single-component organic conductors based on neutral radicals containing the pyrazino-TCNQ skeleton

  摘要：

  Pyrazino-TCNQ (1a) prepared from 5,8-diiodoquinoxaline (4a) is, like TCNQ itself, a strong electron acceptor and gives a stable anion radical salt as well as highly conductive charge-transfer crystals with donors. Substituted derivatives 1b-i were similarly prepared from 3,6-diiodo-1,2-phenylenediamine (5) as a common intermediate, and bulky substituents such as the phenyl or pyridyl groups have very little effect on either the redox properties or planar geometry of la. Neutral radicals 3d-g derived from pyridyl-substituted derivatives 1d-g, respectively, are open-shell donor-pi-acceptor systems with high electrical amphotericity designed as a new motif for single-component organic conductors. The powder conductivity of 3f was as high as 3.2 X 10(-5) S cm-1.

  DOI：

  10.1021/jo00051a015

文献信息

• Supramolecular nanopatterns of H-shaped molecules
  作者：Melissa Hündgen、Katharina A. Maier、Sigurd Höger、Stefan-S. Jester

  DOI：10.1039/c8cc04403a

  日期：——

  H-shaped arylene–alkynylene scaffolds form brick-like patterns on graphite, as shown via scanning-tunneling microscopy.

  H形芳基-炔基支架在石墨上形成类似砖块的图案，如通过扫描隧道显微镜所示。
• Diversely Substituted Quinolines via Rhodium-Catalyzed Alkyne Hydroacylation
  作者：James D. Neuhaus、Sarah M. Morrow、Michael Brunavs、Michael C. Willis

  DOI：10.1021/acs.orglett.6b00390

  日期：2016.4.1

  hydroacylative union of aldehydes and o-alkynyl anilines leads to 2-aminophenyl enones, and onward to substituted quinolines. The mild reaction conditions employed in this chemistry result in a process that displays broad functional group tolerance, allowing the preparation of diversely substituted quinolines in high yields. Extension to the use of o-alkynyl nitro arenes as substrates leads to 2-nitrochalcones

  醛和邻炔基苯胺的Rh催化的氢酰基联合产生2-氨基苯基烯酮，并进一步生成取代的喹啉。在该化学反应中使用的温和反应条件导致显示出宽泛的官能团耐受性的过程，从而可以高收率制备各种取代的喹啉。扩展使用邻炔基硝基芳烃作为底物会产生2-硝基查耳酮，从中可以得到喹啉和喹啉N-氧化物。
• 1,4-Diaryl-7,10-dimethoxyquinoxalino[2,3-<i>b</i>]quinoxalines and Their Dihydro Derivatives: Redox Switching of NIR Absorption and Fluorescence
  作者：Youhei Miura、Hidetoshi Kawai、Kenshu Fujiwara、Takanori Suzuki

  DOI：10.1246/cl.2011.975

  日期：2011.9.5

  Due to the high-lying HOMO of the substituents and the low-lying LUMO inherited by the heterocyclic skeleton, the title quinoxalinoquinoxalines 1 exhibit absorption bands which extend to the NIR region, whereas the dihydro derivatives 2 are less colored but emit strong green fluorescence. Thus, the present pairs can serve as novel redox dyes for drastic spectral changes.

  由于取代基的高位 HOMO 和杂环骨架继承的低位 LUMO，标题中的喹喔啉喹喔啉 1 显示出延伸至近红外区域的吸收带，而二氢衍生物 2 的颜色较浅，但发出强烈的绿色荧光。因此，本对化合物可作为新型氧化还原染料，用于大幅改变光谱。
• Chalcogen Bond versus Halogen Bond: Changing Contributions in Determining the Crystal Packing of Dihalobenzochalcogenadiazoles
  作者：Yusuke Ishigaki、Kai Shimomura、Kota Asai、Takuya Shimajiri、Tomoyuki Akutagawa、Takanori Fukushima、Takanori Suzuki

  DOI：10.1246/bcsj.20220008

  日期：2022.3.15

  In the crystals of 4,7-dihalobenzo[c][1,2,5]chalcogenadiazoles, the molecules are connected by two competing secondary bonding interactions: chalcogen bond (ChB) and halogen bond (HaB). Because the strengths of ChB and HaB change according to the kind of chalcogen (E: S, Se, Te) and halogen (X: Cl, Br, I), their relative contributions in determining the crystal packing can also change. Six newly determined

  在 4,7-二卤代苯并[ c][1,2,5]硫属二唑，分子通过两个相互竞争的二级键相互作用连接：硫属键（ChB）和卤素键（HaB）。由于 ChB 和 HaB 的强度根据硫属元素（E：S、Se、Te）和卤素（X：Cl、Br、I）的种类而变化，它们在确定晶体堆积方面的相对贡献也会发生变化。六种新确定的晶体结构以及 3 种先前报道的结构可分为两组：以 ChB 为主的结构和以 HaB 为主的结构。其中 X = I 的 HaB 足以决定具有 E = S 和 Se 的化合物的晶体堆积，但在 E = Te 的情况下则不然，而其中 X = Cl 或 Br 的 HaB 对晶体中以 ChB 为主的分子网络几乎没有影响.
• Tuning Molecular Electron Affinities against Atomic Electronegativities by Spatial Expansion of a π‐System
  作者：Elena A. Chulanova、Ekaterina A. Radiush、Nikolay A. Semenov、Emanuel Hupf、Irina G. Irtegova、Yulia S. Kosenkova、Irina Yu. Bagryanskaya、Leonid A. Shundrin、Jens Beckmann、Andrey V. Zibarev

  DOI：10.1002/cphc.202200876

  日期：——

  2,1,3-benzochalcogenadiazoles C6R4N2E and C6H2R2N2E (E=S, Se, Te; R=H, F, Cl, Br, I) lighter/smaller E and non-hydrogen R atoms with heavier/bigger, i. e., decreasing atomic electronegativities, increases molecular electron affinities.

  大小很重要：替换为 2,1,3-苯并硫属二唑 C 6 R 4 N 2 E 和 C 6 H 2 R 2 N 2 E（E=S、Se、Te；R=H、F、Cl、Br、I ) 较轻/较小的 E 和非氢 R 原子，较重/较大，i。即，降低原子电负性，增加分子电子亲和力。