spiro[indoline-phenanthrolinoxazine] | 151329-44-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: spiro[indoline-phenanthrolinoxazine]
• 英文别名: 1',3',3'-Trimethylspiro[[1,4]oxazino[2,3-f][1,10]phenanthroline-2,2'-indole]
• CAS: 151329-44-1
• 化学式: C₂₄H₂₀N₄O
• 分子量: 380.449
• InChiKey: AHFZQFFXWVLSFL-UHFFFAOYSA-N

物化性质

• 沸点：
  625.4±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  spiro[indoline-phenanthrolinoxazine] 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Photochromism of Spirooxazines in Homogeneous Solution and Phospholipid Liposomes

  摘要：

  The photochromic behavior of several spirooxazines (SO) containing phenanthrene or phenanthroline moieties in the oxazine part of molecules has been investigated in several solvents and phosphatidylcholine (PC) liposomes. The solvatochromic properties of the merocyanine (MC) forms of these dyes were used to probe their location within the PC membrane. Transient spectroscopic measurements revealed that, when first formed by photoexcitation, the MC form of phenanthroline-containing spirooxazines were located at relatively nonpolar sites within the membrane, but they subsequently moved to a more polar environment typical of the aqueous-organic interface. The characteristic time for this intersite movement was tau approximate to 10(-3) s, corresponding to a diffusion coefficient of D approximate to 10(-11) cm(2) s(-1). In contrast, these spectral shifts were not observed when PC liposome-bound SO containing the phenanthrene moiety were photoexcited, suggesting that either intersite diffusion was more rapid for these compounds or the initially formed MC (and its spiro precursor) were located in a more polar microenvironment. The rate of thermal ring-closing following UV photoexcitation decreased modestly when either an electron-withdrawing group was present on the MC oxazine ring or an electron-donating group was present on the MC indoline ring. A dramatic increase in the ring-closing rate was observed for an o-phenanthroline-containing SO coordinated to a Ru(bpy)(2)(2+) metal center, an effect attributable to strong donation of electron density from the Ru(II) d-orbitals into the ligand pi*-orbitals.

  DOI：

  10.1021/ja9825985
• 作为产物：
  描述：

  5-methoxy-1,10-phenanthroline 在 盐酸 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 spiro[indoline-phenanthrolinoxazine]
  参考文献：
  名称：

  Solvatochromic and photochromic characteristics of new 1,3-dihydrospiro[2H-indole-2,2′-[2H]-bipyrido[3,2-f][2,3-h][1,4]benzoxazines]

  摘要：

  The mono-oxime of 1,10-phenanthroline-5,6-quinone reacts with 1,3,3-trimethyl-2-methyleneindoline derivatives to give the corresponding spirooxazines, i.e. 1,3-dihydrospiro[2H-indole-2,2'-[2H]-bipyrido[3,2-f][2,3-h][1,4)benzoxazines]. These compounds exhibit particular solvatochromic behaviour, strongly dependent on the substitution pattern. At room temperature and without any light excitation, an equilibrium is established between closed and opened forms. The photochromic characteristics have been determined using flash photolysis coupled to a fast scanning spectrometer allowing the determination of rate constants for thermal bleaching, visible absorption and photocoloration. The coloured opened forms, either photoinduced or arising from the solvation effect, appear to be spectroscopically identical. Structural parameters of the short-lived photomerocyanines have also been obtained.

  DOI：

  10.1039/p29930001327

文献信息

• A Solution- and Solid-State Investigation of Medium Effects on Charge Separation in Metastable Photomerocyanines
  作者：Dinesh G. Patel、Michelle M. Paquette、Roni A. Kopelman、Werner Kaminsky、Michael J. Ferguson、Natia L. Frank

  DOI：10.1021/ja100238h

  日期：2010.9.15

  zwitterionic structure in high-polarity solvents. The effect of azahomoadamantyl substitution is explored by comparing 1 and 2 with the analogous indolyl derivatives, spiro[indoline-isoquinolinoxazine] (3) and spiro[indoline-phenanthrolinoxazine] (4) through XRD analysis of the closed spirooxazine (SO) forms, solution-state kinetic experiments, solvatochromism, and NMR studies. Longer C(spiro)-O bond lengths

  研究了溶液状态介电和分子间相互作用对亚稳态螺恶嗪光部花青 (PMC) 中电荷分离程度的影响。我们报告了两种衍生物中螺恶嗪类光致变色分子的开放形式亚稳态光部花青的首次 X 射线衍射 (XRD) 分析：螺[氮杂高金刚烷-异喹啉恶嗪] (1) 和螺[氮杂高金刚烷-菲咯啉恶嗪] (2 ）。使用开放光部花青形式的 XRD 分析结果，结合计算、溶剂化变色和溶液 NMR 研究，我们研究了介质对这些光部花青基态结构的影响。1 和 2 的溶剂致变色和 NMR 化学位移研究支持指定非极性溶剂中的醌式结构和高极性溶剂中的两性离子结构。通过将 1 和 2 与类似的吲哚衍生物、螺[二氢吲哚-异喹啉恶嗪] (3) 和螺[二氢吲哚-菲咯啉恶嗪] (4) 进行比较，通过对封闭螺恶嗪 (SO) 形式、溶液的 XRD 分析来探索氮杂高金刚烷基取代的影响-状态动力学实验、溶剂化变色和核磁共振研究。SO 形式中较长的 C(螺)-O
• Promoted colorimetric response of spirooxazine derivative: a simple assay for sensitive mercury(II) detection
  作者：Jinfeng Ji、Guangliang Song、Xiao Cai、Jinyang Hu、Liang Feng、Hongjun Zhu

  DOI：10.1007/s11164-015-2389-3

  日期：2016.6

  A spirooxazine derivative 1,3-dihydro-1,3,3-trimethyl-spiro[2- H -indole-2-2′-[2 H -1,4] oxazino [2,3- f ] [1, 10] phenanthroline] (compound 1 ) was explored as a sensitive Hg2+ probe. Sensing behavior toward various metal ions including Hg2+, Na+, K+, Ag+, Pb2+, Ni2+, Fe2+, Cu2+, Zn2+, Cd2+, Co2+, Ba2+, Mn2+, Cr3+, Al3+ and Fe3+ was investigated by UV–Vis in acetonitrile solution. Benefiting from

  螺恶嗪衍生物1,3-二氢-1,3,3-三甲基-螺[2- H- 吲哚-2-2'-[2 H -1,4]恶嗪[2,3- f ] [ 1，10 []菲咯啉]（化合物 1 ）被用作敏感的Hg 2+探针。对Hg 2 +，Na +，K +，Ag +，Pb 2 +，Ni 2 +，Fe 2 +，Cu 2 +，Zn 2 +，Cd 2 +，Co 2 +，Ba 2等各种金属离子的传感行为+，Mn 2 +，Cr 3+，Al 3+Fe 3+在乙腈溶液中通过UV-Vis进行了研究。受益于视觉检测策略，该化合物对Hg 2+表现出较好的选择性和灵敏度，检测极限为0.68 ppm。此外，当将不同浓度的汞离子（10 -8 –10 -2 M）滴入探针（化合物 1 ）时，溶液的颜色也不同。用肉眼可以很容易地观察到这种显着的颜色变化（从淡紫色到绿色）。该方法不仅可以检测乙腈溶液中的Hg 2+，还可以检测污水和工业废水中的Hg 2+。
• Cyclometalated iridium(III) complex containing indolinyl-based phenanthroline ligand: Synthesis, structure and photophysical properties
  作者：Jia Wang、Senqiang Zhu、Rui Liu、Meng Tang、Huan Su、Xiao Cai、Hongjun Zhu

  DOI：10.1016/j.ica.2019.04.009

  日期：2019.6

  Abstract A heteroleptic cationic Ir(III) complex [(X)2Ir(L)]+PF6− was designed and synthesized, where L = 2-(1,3,3-trimethylindolin-2-yl)oxazolo[4,5-f] [1,10]phenanthroline, X = 2-phenylpyridine (ppy). Its structural and photophysical properties have been systematically investigated via a series of spectroscopic methods. This complex exhibits ligand-localized 1π,π* transitions below 350 nm, broad and

  摘要设计合成了L = 2-（1,3,3-trimethylindolin-2-yl）oxazolo [4,5-]的杂合阳离子Ir（III）络合物[（X）2Ir（L）] + PF6-。 f] [1，10]菲咯啉，X ＝ 2-苯基吡啶（ppy）。它的结构和光物理性质已通过一系列光谱方法进行了系统研究。该复合物在350 nm以下具有配体局部化的1π，π*跃迁，在350至450 nm之间具有宽广且无结构的金属到配体/配体到配体的电荷转移（1MLCT / 1LLCT）跃迁，以及自旋禁止的3MLCT / 3LLCT /3π，π*在450 nm以上跃迁。在其最大吸收处激发后，该络合物在溶液中显示出橙色磷光。另外，该络合物在可见光谱区域表现出强烈的激发态吸收，良好的抗光漂白性和电化学稳定性。
• Photoprocesses and magnetic behavior of photochromic transition metal indoline[phenanthrolinospirooxazine] complexes: Tunable photochromic materials
  作者：Roni A. Kopelman、Michelle M. Paquette、Natia L. Frank

  DOI：10.1016/j.ica.2008.03.079

  日期：2008.9

  We have synthesized a series of M(IPSO) 3 (BPh 4 ) 2 complexes consisting of first row transition metals and a photochromic phenanthroline ligand: (M = Mn(II), Fe(II), Co(II), Ni(II), Zn(II), and Cu(II), IPSO = spiro[indole-phenanthrolinoxazine]). The optical properties associated with photochromic behavior were evaluated by determination of the (i) equilibrium constants ( K ) for the thermal and photostationary

  摘要我们合成了一系列由第一行过渡金属和光致变色菲咯啉配体组成的M（IPSO）3（BPh 4）2配合物：（M = Mn（II），Fe（II），Co（II），Ni（ II），Zn（II）和Cu（II），IPSO =螺[吲哚-菲咯啉恶嗪]）。通过确定（i）热态和光平稳态的平衡常数（K），（ii）光化学开环和闭环的速率以及（iii）热环的速率来评估与光致变色行为相关的光学性质-关闭。与金属的配位作用大大提高了与从无色螺恶嗪转化为有色光merocyanine异构体相关的光致变色性值。
• [EN] MAGNETICALLY BISTABLE COMPLEXES AND DEVICES AND METHODS OF MAKING AND USING THE SAME<br/>[FR] COMPLEXES BISTABLES MAGNÉTIQUEMENT ET DISPOSITIFS ET PROCÉDÉS DE PRÉPARATION ET D'UTILISATION DE CEUX-CI
  申请人：UVIC IND PARTNERSHIPS INC

  公开号：WO2017015765A1

  公开（公告）日：2017-02-02

  Disclosed herein are embodiments of complexes exhibiting reversible light-induced magnetization switching with unprecedented lifetimes. In particular embodiments, the complexes are provided as organic thin films that can exhibit long lifetimes at ambient temperatures. In some representative embodiments, the complex comprises an electronically bistable cobalt complex functionalized with an optically bistable ligand. A photoisomerization-induced spin–charge excited state (PISCES) process can occur, resulting in the direct observation of light-induced spin state switching at room temperature in the solid state.

  本文公开了一些具有前所未有的寿命的可逆光诱导磁化开关复合物的实施例。在特定的实施例中，这些复合物被提供为有机薄膜，在常温下可以展示长寿命。在一些代表性的实施例中，该复合物包括一种电子双稳态钴配合物，其被光学双稳态配体功能化。可以发生光异构化诱导自旋-电荷激发态（PISCES）过程，导致在固态下直接观察到室温下光诱导自旋态转换。