4,4,5,5,5-pentafluoro-1-(1',10'-phenanthrolin-2'-yl)pentane-1,3-dione | 1018984-29-6

• 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: 4,4,5,5,5-pentafluoro-1-(1',10'-phenanthrolin-2'-yl)pentane-1,3-dione
• 英文别名: Hphen5f；Hphe5f；4,4,5,5,5-Pentafluoro-1-(1,10-phenanthroline-2-yl)pentane-1,3-dione；4,4,5,5,5-pentafluoro-1-(1,10-phenanthrolin-2-yl)pentane-1,3-dione
• CAS: 1018984-29-6
• 化学式: C₁₇H₉F₅N₂O₂
• 分子量: 368.263
• InChiKey: OMVJNPJSFGGSAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  europium(III) chloride hexahydrate 、 4,4,5,5,5-pentafluoro-1-(1',10'-phenanthrolin-2'-yl)pentane-1,3-dione 在 NaOH 作用下， 以 乙醇 为溶剂， 生成 tris(4,4,5,5,5-pentafluoro-1-(1',10'-phenanthrolin-2'-yl)pentane-1,3-dionato)europium(III) tetrahydrate
  参考文献：
  名称：

  Highly Efficient Sensitized Red Emission from Europium (III) in Ir−Eu Bimetallic Complexes by ³MLCT Energy Transfer

  摘要：

  Two novel iridium-europium bimetallic complexes, {[(dfppy)(2)Ir(mu-phen5f)](3)EuCl}Cl-2 and (dfppy)(2)Ir(,mu-phen5f)Eu(TFAcA)(3) [dfppy represents 2-(4',6'-difluorophenyl)-pyridinato-N,C-2', phen5f stands for 4,4,5,5,5-pentafluoro-1-(1',10'-phenanthrolin-2'-yi)-pentane-1,3-dionate and TFAcA represents trifluoroacetylacetonate], were successfully synthesized. The novel ligand Hphen5f with four coordination sites was designed as a bridge to link the Ir-III center and the Eu-III center. The X-ray diffraction data shows that the nonbonding distances for Eu... Ir are 6.028, 5.907, and 6.100 A in the bimetallic complex {[(dfppy)(2)Ir(mu-phen5f)](3)EuCl}Cl-2, Photophysical studies implied that the high efficient red luminescence from the Eu-III ion was sensitized by the (MLCT)-M-3 (metal-to-ligand charge transfer) energy based on an Ir-III complex-ligand in a d-f bimetallic assembly. The excitation window for the new bimetallic complex {[(dfppy)(2)Ir(mu-phen5f)](3)EuCl}Cl-2 extends up to 530 nm (1 x 10(-3) M in EtOH), indicating that this bimetallic complex can emit red light under the irradiation of sunlight.

  DOI：

  10.1021/ic701817n

文献信息

• Sensitised near-infrared emission from lanthanides using an iridium complex as a ligand in heteronuclear Ir2Ln arrays
  作者：Fang-Fang Chen、Zu-Qiang Bian、Bin Lou、En Ma、Zhi-Wei Liu、Dao-Bo Nie、Zhu-Qi Chen、Jiang Bian、Zhong-Ning Chen、Chun-Hui Huang

  DOI：10.1039/b810016k

  日期：——

  The iridium(III) complex Ir(ppy)2(phen5f) [ppy = 2-phenylpyridinato-N,C2′, and phen5f = 4,4,5,5,5-pentafluoro-1-(1′,10′-phenanthrolin-2′-yl)-pentane-1,3-dionate] has been synthesised and used as “complex ligands” to make heteronuclear d–f complexes by the attachment of Ln(NO3)3·xH2O at the vacant coordination sites in the bridging ligand phen5f. The microanalyses and crystal structure characteristics confirmed the formation of the heteronuclear Ir2Ln arrays. The measurement of the lowest triplet state energy level of Ir(ppy)2(phen5f) indicates that it is suitable for the NIR (near-infrared) lanthanide ions, NdIII, YbIIIand ErIII. Upon irradiation of the MLCT (metal-to-ligand charge transfer) absorption of Ir(ppy)2(phen5f) at an excitation wavelength from 380–490 nm, the characteristic emission spectra of the three Ir2Ln arrays (Ln = Nd, Yb, Er) in both the solid state and in CH3CN solution were measured. According to the results, more IrIII complexes will be designed for lanthanide NIR emission by the proper combination between the cyclometalated ligand and the tetradentate ancillary ligand.

  合成了铱(III)配合物Ir(ppy)2(phen5f) [ppy = 2-苯基吡啶-N,C2'，phen5f = 4,4,5,5,5-五氟-1-(1′,10′-菲啰啉-2′-基)-戊二酸-1,3-二酯]，并作为“配体复合物”以在桥联配体phen5f的空位配位位点上附加Ln(NO3)3·xH2O，从而制造异核d–f配合物。微量分析和晶体结构特征确认了异核Ir2Ln阵列的形成。测量Ir(ppy)2(phen5f)的最低三重态能级表明其适用于近红外(NIR)的镧系离子NdIII、YbIII和ErIII。在380–490 nm的激发波长下，照射Ir(ppy)2(phen5f)的金属-配体电荷转移(MLCT)吸收，测量了三种Ir2Ln阵列(Ln = Nd, Yb, Er)在固态和CH3CN溶液中的特征发射光谱。根据结果，通过合适结合环金属配体和四齿辅助配体，更多的IrIII配合物将被设计用于镧系NIR发射。
• Sensitized near-infrared emission of YbIII from an IrIII–YbIII bimetallic complex
  作者：Dan Li、Fang-Fang Chen、Zu-Qiang Bian、Zhi-Wei Liu、Yong-Liang Zhao、Chun-Hui Huang

  DOI：10.1016/j.poly.2008.12.043

  日期：2009.4

  A new cyclometalated ligand 1.3-dimethyl-5-phenyi-1H-[ 1,2,4]-triazole (pdt) was designed and synthesized. And the corresponding it complex Ir(pdt)(2)(phen5f) (phen5f stands for 4,4,5.5.5-pentafluoro-1-(1',10'-phenanthrolin-2'-yl)-pentane-1,3-dionate) was obtained. According to the measurement of the lowest triplet state energy level of Ir(pdt)(2)(phen5o, it is suitable for sensitizing NIR (near-infrared) Ianthanide ions instead of Eu-III. The bimetallic complex [(pdt)(2)Ir(mu-phen5f)YbCl2 center dot 2CH(3)CH(2)OH - H2O]Cl was synthesized by the approach of "complexes as ligands". Data showed that the emission quenching was observed in the solid state when the Ir-III-Yb-III complex was compared with the Ir-III complex, which implied that energy transfer might occur from It complex-ligand to Yb-III ion. Upon irradiation of the MLCT (metal-to-ligand charge transfer) absorption of Ir(pdt)(2)(phen5f), the characteristic emission of Yb-III was obtained with the peak around 978 nm. (C) 2009 Elsevier Ltd. All rights reserved.
• Highly Efficient Sensitized Red Emission from Europium (III) in Ir−Eu Bimetallic Complexes by ³MLCT Energy Transfer
  作者：Fang-Fang Chen、Zu-Qiang Bian、Zhi-Wei Liu、Dao-Bo Nie、Zhu-Qi Chen、Chun-Hui Huang

  DOI：10.1021/ic701817n

  日期：2008.4.1

  Two novel iridium-europium bimetallic complexes, [(dfppy)(2)Ir(mu-phen5f)](3)EuCl}Cl-2 and (dfppy)(2)Ir(,mu-phen5f)Eu(TFAcA)(3) [dfppy represents 2-(4',6'-difluorophenyl)-pyridinato-N,C-2', phen5f stands for 4,4,5,5,5-pentafluoro-1-(1',10'-phenanthrolin-2'-yi)-pentane-1,3-dionate and TFAcA represents trifluoroacetylacetonate], were successfully synthesized. The novel ligand Hphen5f with four coordination sites was designed as a bridge to link the Ir-III center and the Eu-III center. The X-ray diffraction data shows that the nonbonding distances for Eu... Ir are 6.028, 5.907, and 6.100 A in the bimetallic complex [(dfppy)(2)Ir(mu-phen5f)](3)EuCl}Cl-2, Photophysical studies implied that the high efficient red luminescence from the Eu-III ion was sensitized by the (MLCT)-M-3 (metal-to-ligand charge transfer) energy based on an Ir-III complex-ligand in a d-f bimetallic assembly. The excitation window for the new bimetallic complex [(dfppy)(2)Ir(mu-phen5f)](3)EuCl}Cl-2 extends up to 530 nm (1 x 10(-3) M in EtOH), indicating that this bimetallic complex can emit red light under the irradiation of sunlight.