spiro[9H-fluorene-9,3'-[3H]-pyrazole]-4',5'-dicarbonitrile | 23227-70-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: spiro[9H-fluorene-9,3'-[3H]-pyrazole]-4',5'-dicarbonitrile
• 英文别名: spiro[fluorene-9,3'-[3H]pyrazole]-4',5'-dicarbonitrile；4',5'-dicyanospiro[9H-fluoren-9,3'-[3H]-pyrazole]；fluorenespirodicyanopyrazole；spiro[fluorene-9,3'-pyrazole]-4',5'-dicarbonitrile；Spiro[fluorene-9,5'-pyrazole]-3',4'-dicarbonitrile
• CAS: 23227-70-5
• 化学式: C₁₇H₈N₄
• 分子量: 268.277
• InChiKey: QOQCDZASZNGMFC-UHFFFAOYSA-N

物化性质

• 沸点：
  467.8±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  spiro[9H-fluorene-9,3'-[3H]-pyrazole]-4',5'-dicarbonitrile 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Duerr, Heinz; Thome, Alfred; Steiner, Ulrich, Journal of the Chemical Society. Chemical communications, 1988, # 5, p. 338 - 340

  摘要：

  DOI：

文献信息

• Photochromic Control of Photoinduced Electron Transfer. Molecular Double-Throw Switch
  作者：Stephen D. Straight、Joakim Andréasson、Gerdenis Kodis、Ana L. Moore、Thomas A. Moore、Devens Gust

  DOI：10.1021/ja044128i

  日期：2005.3.1

  that employs a photochromic moiety to direct photoinduced electron transfer from an excited state donor down either of two pathways has been prepared. The molecular triad consists of a free base porphyrin (P) linked to both a C(60) electron acceptor and a dihydroindolizine (DHI) photochrome. Excitation of the porphyrin moiety of DHI-P-C(60) results in photoinduced electron transfer with a time constant

  已经制备了一种分子双掷开关，该开关采用光致变色部分将光诱导电子从激发态供体转移到两种途径中的任何一种。分子黑社会由连接到 C(60) 电子受体和 dihydroindolizine (DHI) 光致变色的游离碱卟啉 (P) 组成。DHI-PC(60) 卟啉部分的激发导致光致电子转移，时间常数为 2.3 ns，得到 DHI-P(*)(+)-C(60)(*)(-) 电荷分离量子产率为 82%。UV (366 nm) 光将 DHI 部分光异构化为甜菜碱 (BT) 形式，其具有比 DHI 更高的还原潜力。BT-PC(60) 卟啉的激发之后是光致电子转移，时间常数为 56 ps，以 99% 的产率产生 BT(*)(-)-P(*)(+)-C(60) . BT-PC(60) 异构化回 DHI-PC(60) 可以通过可见光或热来实现。因此，源自卟啉的光致电荷分离通过二氢茚茚的光异构化被可逆地引导至两种不同途径中的任一种。开关可以循环多次。
• A New Photochromic 8π-System Based on an Azaheptatriene-Tetrahydroazepinoisoquinoline Electrocyclization
  作者：Yongsheng Tan、Thomas Hartmann、Volker Huch、Heinz Dürr、Pierre Valat、Veronique Wintgens、Jean Kossanyi

  DOI：10.1021/jo000807+

  日期：2001.2.1

  A new photochromic family of tetrahydroazepinoisoquinolines (THAI) 4a-i has been prepared. It undergoes light-induced ring opening from spiro compounds 4 to betaines 3 that decolorize in a very fast cyclizing reaction. Depending on substitution of the precursors 1 and 6, the photochromic styryltetrahydroindolizines (THI) 5k-q are formed in a periselective way. The conformation and configuration of

  已经制备了四氢氮杂庚烯异喹啉（THAI）4a-i的新光致变色家族。它经历了从螺化合物4到甜菜碱3的光诱导开环，甜菜碱3在非常快速的环化反应中脱色。取决于前体1和6的取代，以变态选择性的方式形成光致变色的苯乙烯基四氢吲哚并嗪（THI）5k-q。通过核磁共振研究了新的光致变色THAI 4和THI 5的构象和构型，并通过X射线分析证明了这两种化合物的结构。通过激光闪光光解研究了光致变色性质，其提供了彩色形式3和3'的寿命在微秒或纳秒范围内。
• Photonic Control of Photoinduced Electron Transfer via Switching of Redox Potentials in a Photochromic Moiety
  作者：Yuichi Terazono、Gerdenis Kodis、Joakim Andréasson、Goojin Jeong、Alicia Brune、Thomas Hartmann、Heinz Dürr、Ana L. Moore、Thomas A. Moore、Devens Gust

  DOI：10.1021/jp037005d

  日期：2004.2.1

  linked to a photochromic dihydroindolizine moiety (DHI) to form a P-DHI dyad. When the dihydroindolizine is in its closed, spirocyclic form (DHIc), the photophysics of the attached porphyrin are unaffected. Irradiation with UV light opens the photochromic moiety to the betaine form (DHIo), which has a significantly higher reduction potential than DHIc. Light absorption by the porphyrin moiety of P-DHIo

  卟啉 (P) 已与光致变色二氢中氮茚部分 (DHI) 共价连接以形成 P-DHI 二元组。当二氢中氮茚处于其封闭的螺环形式 (DHIc) 时，附着的卟啉的光物理不受影响。用紫外线照射将光致变色部分打开为甜菜碱形式 (DHIo)，其还原电位明显高于 DHIc。P-DHIo 的卟啉部分的光吸收之后是快速 (50 ps) 光诱导电子转移，以产生 P.+-DHIo(.-) 电荷分离状态。该状态在 2.9 ps 内重新组合以形成基态。用波长 > 590 nm 的光照射 P-DHIo 会诱导光异构化回 P-DHIc。也可以实现热闭合。因此，光用于打开或关闭光致电子转移。
• Synthesis of IR-sensitive photoswitchable molecules: photochromic 9?- styrylquinolinedihydroindolizines
  作者：Saleh A. Ahmed、Thomas Hartmann、Volker Huch、Heinz D�rr、Aboel-Magd A. Abdel-Wahab

  DOI：10.1002/1099-1395(200009)13:9<539::aid-poc296>3.0.co;2-9

  日期：2000.9

  New mono-(5a-t, w) and biphotochromic (5u, v) 9'-styrylquinolinespirodihydroindolizines (DHIs) with IR-absorbing colored forms (4) were prepared. The conformation and configuration of these new DHIs were investigated by NMR studies and the structure was proved by x-ray analysis. The kinetics of the fast cyclizing process of betaine 4 to DI-II 5 takes place in the millisecond range and were studied by flash photolysis. The absorption bands of the betaines 4 were recorded at low temperature by FT-UV/VIS/near-IR spectroscopy. Large solvent effects on the absorption maxima of betaines 4 were observed. Copyright (C) 2000 John Wiley & Sons, Ltd.
• Gross, Hubert; Duerr, Heinz, Angewandte Chemie, 1982, vol. 94, # 3, p. 204
  作者：Gross, Hubert、Duerr, Heinz

  DOI：——

  日期：——