4-methylspiro[4-azahomoadamantane-5,2'-[2H-1,4]ox-azino-[2,3-f][1,10]phenanthroline] | 1242264-84-1

• 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: 4-methylspiro[4-azahomoadamantane-5,2'-[2H-1,4]ox-azino-[2,3-f][1,10]phenanthroline]
• 英文别名: spiro[azahomoadamantane-phenanthrolinoxazine]；4-Methylspiro[4-azatricyclo[4.3.1.13,8]undecane-5,2'-[1,4]oxazino[2,3-f][1,10]phenanthroline]；4-methylspiro[4-azatricyclo[4.3.1.13,8]undecane-5,2'-[1,4]oxazino[2,3-f][1,10]phenanthroline]
• CAS: 1242264-84-1
• 化学式: C₂₄H₂₄N₄O
• 分子量: 384.481
• InChiKey: YAUTZDPFWKGSOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  4-methylspiro[4-azahomoadamantane-5,2'-[2H-1,4]ox-azino-[2,3-f][1,10]phenanthroline] 以 乙腈 为溶剂， 反应 0.01h， 生成 4-methylspiro[4-azahomoadamantane-5,2’-[2H-1,4]ox-azino-[2,3-f][1,10]phenanthroline]
  参考文献：
  名称：

  Modulating Short Wavelength Fluorescence with Long Wavelength Light

  摘要：

  Two molecules in which the intensity of shorter-wavelength fluorescence from a strong fluorophore is modulated by longer-wavelength irradiation of an attached merocyanine-spirooxazine reverse photochromic moiety have been synthesized and studied. This unusual fluorescence behavior is the result of quenching of fluorophore fluorescence by the thermally stable, open, zwitterionic form of the spirooxazine, whereas the photogenerated closed, spirocyclic form has no effect on the fluorophore excited state. The population ratio of the closed and open forms of the spirooxazine is controlled by the intensity of the longer-wavelength modulated light. Both square wave and sine wave modulation were investigated. Because the merocyanine-spirooxazine is an unusual reverse photochrome with a thermally stable long-wavelength absorbing form and a short-wavelength absorbing photogenerated isomer with a very short lifetime, this phenomenon does not require irradiation of the molecules with potentially damaging ultraviolet light, and rapid modulation of fluorescence is possible. Molecules demonstrating these properties may be useful in fluorescent probes, as their use can discriminate between probe fluorescence and various types of adventitious "autofluorescence" from other molecules in the system being studied.

  DOI：

  10.1021/ja504879p
• 作为产物：
  描述：

  以 乙腈 为溶剂， 生成 4-methylspiro[4-azahomoadamantane-5,2'-[2H-1,4]ox-azino-[2,3-f][1,10]phenanthroline]
  参考文献：
  名称：

  介质对亚稳态光部花青电荷分离影响的溶液和固态研究

  摘要：

  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

  DOI：

  10.1021/ja100238h

文献信息

• [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。
• Determining the Magnitude and Direction of Photoinduced Ligand Field Switching in Photochromic Metal–Organic Complexes: Molybdenum–Tetracarbonyl Spirooxazine Complexes
  作者：Michelle M. Paquette、Brian O. Patrick、Natia L. Frank

  DOI：10.1021/ja109776z

  日期：2011.7.6

  light-induced isomerization of photochromic ligands. Changes in ligand field between the ring-closed spirooxazine (SO) and ring-opened photomerocyanine (PMC) forms of photochromic azahomoadamantyl and indolyl phenanthroline-spirooxazine ligands are demonstrated through FT-IR, (13)C NMR, and computational studies of their molybdenum-tetracarbonyl complexes. The frontier molecular orbitals (MOs) of the SO and PMC

  用光致变色金属配体配合物对过渡金属的固有特性（例如氧化还原电位、发射/吸收能和自旋态）进行光学切换或调整的能力是开发“智能”材料的重要策略。我们描述了使用金属羰基配合物作为与光致变色配体的光致异构化相关的配体场变化的光谱探针的方法。通过 FT-IR、(13)C NMR 及其钼的计算研究证明了闭环螺恶嗪 (SO) 和开环光部花青 (PMC) 形式的光致变色氮杂高金刚烷基和吲哚基菲咯啉-螺恶嗪配体之间配体场的变化-四羰基配合物。SO 和 PMC 形式的前沿分子轨道 (MO) 在电子密度分布和能量方面有很大不同。在 SO 和 PMC 形式的配体中的多个 π* MO 中，LUMO+1，一种基于伪 b(1)-对称菲咯啉的 MO，主要与 Mo(CO)(4) 片段混合并提供Mo(d)→phen(π*) 反键的主要途径。发现 LUMO+1 在 SO 形式中的能量比 PMC 形式低 0.2-0.3 eV，表明
• BISTABLE COMPLEXES AND DEVICES AND METHODS OF MAKING AND USING THE SAME
  申请人：Frank Natia L.

  公开号：US20180179241A1

  公开（公告）日：2018-06-28

  Disclosed herein are embodiments of complexes exhibiting reversible light-induced magnetization, and/or heat, and/or electrically-induced 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.
• 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
• Modulating Short Wavelength Fluorescence with Long Wavelength Light
  作者：Graeme Copley、Jason G. Gillmore、Jeffrey Crisman、Gerdenis Kodis、Christopher L. Gray、Brian R. Cherry、Benjamin D. Sherman、Paul A. Liddell、Michelle M. Paquette、Laimonas Kelbauskas、Natia L. Frank、Ana L. Moore、Thomas A. Moore、Devens Gust

  DOI：10.1021/ja504879p

  日期：2014.8.27

  Two molecules in which the intensity of shorter-wavelength fluorescence from a strong fluorophore is modulated by longer-wavelength irradiation of an attached merocyanine-spirooxazine reverse photochromic moiety have been synthesized and studied. This unusual fluorescence behavior is the result of quenching of fluorophore fluorescence by the thermally stable, open, zwitterionic form of the spirooxazine, whereas the photogenerated closed, spirocyclic form has no effect on the fluorophore excited state. The population ratio of the closed and open forms of the spirooxazine is controlled by the intensity of the longer-wavelength modulated light. Both square wave and sine wave modulation were investigated. Because the merocyanine-spirooxazine is an unusual reverse photochrome with a thermally stable long-wavelength absorbing form and a short-wavelength absorbing photogenerated isomer with a very short lifetime, this phenomenon does not require irradiation of the molecules with potentially damaging ultraviolet light, and rapid modulation of fluorescence is possible. Molecules demonstrating these properties may be useful in fluorescent probes, as their use can discriminate between probe fluorescence and various types of adventitious "autofluorescence" from other molecules in the system being studied.