[5,6-Dimethyl-1-(4-methylphenyl)benzimidazol-2-yl]-diphenylphosphane | 1435949-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: [5,6-Dimethyl-1-(4-methylphenyl)benzimidazol-2-yl]-diphenylphosphane
• 英文别名: [5,6-dimethyl-1-(4-methylphenyl)benzimidazol-2-yl]-diphenylphosphane
• CAS: 1435949-83-9
• 化学式: C₂₈H₂₅N₂P
• 分子量: 420.494
• InChiKey: ABUZTTKNKQTABH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  copper(l) iodide 、 [5,6-Dimethyl-1-(4-methylphenyl)benzimidazol-2-yl]-diphenylphosphane 、 三苯基膦 以 二氯甲烷 为溶剂， 反应 12.0h， 以84%的产率得到[(2-(diphenylphosphino)-5,6-dimethyl-1-p-tolyl-1H-benzo[d]-imidazole)(triphenylphosphine)2Cu2I2]
  参考文献：
  名称：

  Heteroleptic, Dinuclear Copper(I) Complexes for Application in Organic Light-Emitting Diodes

  摘要：

  A series of highly luminescent, heteroleptic copper(I) complexes has been synthesized using a modular approach based on easily accessible P boolean AND N ligands, triphenylphosphine, and copper(I) halides, allowing for an independent tuning of the emission wavelength with low synthetic efforts. The molecular structure has been investigated via X-ray analysis, confirming a dinuclear copper(I) complex consisting of a butterfly shaped metal-halide cluster and two different sets of ligands. The bidentate P boolean AND N ligand bridges the two metal centers and can be used to tune the energy of the frontier orbitals and therefore the photophysical characteristics, as confirmed by emission spectroscopy and theoretical investigations, whereas the two monodentate triphenylphosphine ligands on the periphery of the cluster core mainly influence the solubility of the complex. By using electron-rich or electron-poor heterocycles as part of the bridging ligand, emission colors can be adjusted, respectively, between yellow (581 nm) and deep blue (451 nm). These complexes have been further investigated in particular with regard to their photophysical properties in thin films and polymer matrix as well as in solution. Furthermore, the suitability of this class of materials for being applied in organic lightemitting diodes (OLEDs) has been demonstrated in a solution-processed device with a maximum current efficiency of 9 cd/A and a low turn-on voltage of 4.1 V using a representative complex as an emitting compound.

  DOI：

  10.1021/cm4018375
• 作为产物：
  描述：

  5,6-二甲基苯并咪唑 在 copper(l) iodide 、 正丁基锂 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 [5,6-Dimethyl-1-(4-methylphenyl)benzimidazol-2-yl]-diphenylphosphane
  参考文献：
  名称：

  Heteroleptic, Dinuclear Copper(I) Complexes for Application in Organic Light-Emitting Diodes

  摘要：

  A series of highly luminescent, heteroleptic copper(I) complexes has been synthesized using a modular approach based on easily accessible P boolean AND N ligands, triphenylphosphine, and copper(I) halides, allowing for an independent tuning of the emission wavelength with low synthetic efforts. The molecular structure has been investigated via X-ray analysis, confirming a dinuclear copper(I) complex consisting of a butterfly shaped metal-halide cluster and two different sets of ligands. The bidentate P boolean AND N ligand bridges the two metal centers and can be used to tune the energy of the frontier orbitals and therefore the photophysical characteristics, as confirmed by emission spectroscopy and theoretical investigations, whereas the two monodentate triphenylphosphine ligands on the periphery of the cluster core mainly influence the solubility of the complex. By using electron-rich or electron-poor heterocycles as part of the bridging ligand, emission colors can be adjusted, respectively, between yellow (581 nm) and deep blue (451 nm). These complexes have been further investigated in particular with regard to their photophysical properties in thin films and polymer matrix as well as in solution. Furthermore, the suitability of this class of materials for being applied in organic lightemitting diodes (OLEDs) has been demonstrated in a solution-processed device with a maximum current efficiency of 9 cd/A and a low turn-on voltage of 4.1 V using a representative complex as an emitting compound.

  DOI：

  10.1021/cm4018375

文献信息

• HETEROLEPTISCHE KUPFER-KOMPLEXE FÜR OPTOELEKTRONISCHE ANWENDUNGEN
  申请人：cynora GmbH

  公开号：EP2780345B1

  公开（公告）日：2017-04-12
• HETEROLEPTIC COPPER COMPLEXES FOR OPTOELECTRONIC USES
  申请人：CYNORA GMBH

  公开号：US20140326981A1

  公开（公告）日：2014-11-06

  A heteroleptic binuclear copper(I) complex of the Cu 2 X 2 (E∩N*)L 2 form, having a structure of formula A: The copper(I) complex may be used in optoelectronic components, particularly for use in organic light emitting diodes (OLEDs).
• US9985225B2
  申请人：——

  公开号：US9985225B2

  公开（公告）日：2018-05-29
• [DE] HETEROLEPTISCHE KUPFER-KOMPLEXE FÜR OPTOELEKTRONISCHE ANWENDUNGEN<br/>[EN] HETEROLEPTIC COPPER COMPLEXES FOR OPTOELECTRONIC USES<br/>[FR] COMPLEXES DE CUIVRE HÉTÉROLEPTIQUES DESTINÉS À DES APPLICATIONS OPTOÉLECTRONIQUES
  申请人：CYNORA GMBH

  公开号：WO2013072508A1

  公开（公告）日：2013-05-23

  Die Erfindung betrifft Kupfer(l)komplexe der Formel mit X* = Cl, Br, I, CN, OCN, SCN, Alkinyl und/oder N3, N*f1E = ein zweibindiger Ligand mit E = Phosphanyl/Arsenyl/Antimonyl-Rest der Form R2E (mit R = Alkyl, Aryl, Heteroaryl, Alkoxyl, Phenoxyl, oder Amid); N* = Imin-Funktion, die Bestandteil einer aromatische Gruppe ist, die ausgewählt ist aus Pyridyl, Pyridazinyl, Pyrimidyl, Pyrazinyl, Triazinyl, Tetrazinyl, Oxazolyl, Thiazolyl, Imidazolyl, Pyrazolyl, Isoxazolyl, Isothiazolyl, 1,2,3-Triazolyl, 1,2,4-Triazolyl, 1,2,4-Oxadiazolyl, 1,2,4-Thiadiazolyl, Tetrazolyl, 1,2,3,4-Oxatriazolyl, 1,2,3,4-Thiatriazolyl, Chinolyl, Isochinolyl, Chinoxalyl, Chinazolyl, die optional weiter substituiert und/oder anneliert sind; "f1" = mindestens ein Kohlenstoffatom, das ebenfalls Bestandteil der aromatischen Gruppe ist, wobei sich das Kohlenstoffatom sowohl direkt benachbart zum Imin-Stickstoffatom als auch zum Phosphor-, Arsen- oder Antimonatom befindet; sowie ihre Verwendung in optoelektronischen Bauelementen.
• Heteroleptic, Dinuclear Copper(I) Complexes for Application in Organic Light-Emitting Diodes
  作者：Daniel M. Zink、Daniel Volz、Thomas Baumann、Mathias Mydlak、Harald Flügge、Jana Friedrichs、Martin Nieger、Stefan Bräse

  DOI：10.1021/cm4018375

  日期：2013.11.26

  A series of highly luminescent, heteroleptic copper(I) complexes has been synthesized using a modular approach based on easily accessible P boolean AND N ligands, triphenylphosphine, and copper(I) halides, allowing for an independent tuning of the emission wavelength with low synthetic efforts. The molecular structure has been investigated via X-ray analysis, confirming a dinuclear copper(I) complex consisting of a butterfly shaped metal-halide cluster and two different sets of ligands. The bidentate P boolean AND N ligand bridges the two metal centers and can be used to tune the energy of the frontier orbitals and therefore the photophysical characteristics, as confirmed by emission spectroscopy and theoretical investigations, whereas the two monodentate triphenylphosphine ligands on the periphery of the cluster core mainly influence the solubility of the complex. By using electron-rich or electron-poor heterocycles as part of the bridging ligand, emission colors can be adjusted, respectively, between yellow (581 nm) and deep blue (451 nm). These complexes have been further investigated in particular with regard to their photophysical properties in thin films and polymer matrix as well as in solution. Furthermore, the suitability of this class of materials for being applied in organic lightemitting diodes (OLEDs) has been demonstrated in a solution-processed device with a maximum current efficiency of 9 cd/A and a low turn-on voltage of 4.1 V using a representative complex as an emitting compound.