6-benzyl-2,2'-bipyridine | 173470-97-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-benzyl-2,2'-bipyridine
• 英文别名: 2-benzyl-6-pyridin-2-ylpyridine
• CAS: 173470-97-8
• 化学式: C₁₇H₁₄N₂
• 分子量: 246.312
• InChiKey: MBDVYGDYVJENRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  387.9±32.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-benzyl-2,2'-bipyridine 以 二氯甲烷 为溶剂， 生成 [PtCl(6-benzyl-2,2'-bipyridine(-1H))]
  参考文献：
  名称：

  10.1002/1099-0682(200012)2000:12<2555::aid-ejic2555<3.0.co;2-z

  摘要：

  DOI：

  10.1002/1099-0682(200012)2000:12<2555::aid-ejic2555<3.0.co;2-z
• 作为产物：
  描述：

  6-溴-2,2'-联吡啶 、 溴甲苯 在 四(三苯基膦)钯 盐酸 、 锌 作用下， 生成 6-benzyl-2,2'-bipyridine
  参考文献：
  名称：

  Proton-Transfer Processes in Well-Defined Media:  Experimental Investigation of Photoinduced and Thermal Proton-Transfer Processes in Single Crystals of 2-(2,4-Dinitrobenzyl)pyridine Derivatives

  摘要：

  A detailed spectroscopic study of photoinduced and thermally activated proton-transfer processes for a series of different crystals of 2-(2,4-dinitrobenzyl)pyridine derivatives has been performed. The quantitative analysis of ground- and excited-state activation barriers and preexponential factors in deuterated and nondeuterated crystals shows clearly that the observed photochromism is linked to a proton-transfer process. Furthermore, it is clearly seen that the supramolecular environment of the transferred proton participates in the proton-transfer process. These supramolecular effects control the relative rates and efficiencies of the observed proton-transfer processes in both the ground and excited state, yielding, at room temperature, photoproducts having lifetimes ranging between hours and weeks. At least two proton-accepting groups may be active in the abstraction of the proton from its relatively stable benzylic position. Additionally, low-temperature measurements of proton-transfer processes show that tunneling processes prevail at temperatures below 100 K only in the excited state. No evidence for tunneling could be found for ground-state processes.

  DOI：

  10.1021/jp9609242

文献信息

• [EN] LUMINESCENT GOLD(III) COMPOUNDS CONTAINING BIDENTATE LIGAND FOR ORGANIC LIGHT-EMITTING DEVICES AND THEIR PREPARATION<br/>[FR] COMPOSÉS AURIQUES (AU TRIVALENT) LUMINESCENTS CONTENTANT UN LIGAND BIDENTATE POUR DISPOSITIFS ÉLECTROLUMINESCENTS ORGANIQUES ET LEUR PRÉPARATION
  申请人：UNIV HONG KONG

  公开号：WO2011006353A1

  公开（公告）日：2011-01-20

  Embodiments of the invention are directed to luminescent gold(III) compounds contains a bidentate ligand with at least one strong σ-donating group, a method of preparation of these compounds and the use of these compounds in organic light emitting devices.. The gold (III) compounds have the chemical structure: Formular (I) wherein: X Is a nitrogen atom; Y is selected from a carbon or a nitrogen atom; A-B is a substituted or unsubstituted cyclometalating ligand (for Y=C) or diimine ligand (for Y=N); where A and B are cyclic structure derivatives; R 1and R2 are optionally substituted carbon donor ligands attached to the gold atom, with the proviso that R1 and R2 are not -CH3, -CH2SiMe3, mesityl, pentaflurophenyl, -CH2C(O)R', -CH(R)SO2CH(R)-, -C6H4N=NC6H5, and wherein R1 and R2 can optionally be combined into a bidentate ligand; and n is greater or equal to zero.

  本发明的实施例涉及含有至少一个强σ-供体基团的双齿配体的发光金(III)化合物，以及制备这些化合物的方法和将这些化合物用于有机发光器件的用途。金(III)化合物具有化学结构：公式(I)，其中：X是氮原子；Y选择自碳或氮原子；A-B是取代或未取代的环金属配体(Y=C)或二亚胺配体(Y=N)，其中A和B是环结构衍生物；R1和R2是附着在金原子上的可选取代碳供体配体，但须注意R1和R2不是-CH3、-CH2SiMe3、mesityl、pentaflurophenyl、-CH2C(O)R'、-CH(R)SO2CH(R)-、-C6H4N=NC6H5，其中R1和R2可以选择性地结合成为双齿配体；n大于或等于零。
• Synthesis and characterization of gold(<scp>III</scp>) adducts and cyclometallated derivatives with 6-benzyl- and 6-alkyl-2,2′-bipyridines
  作者：Maria Agostina Cinellu、Antonio Zucca、Sergio Stoccoro、Giovanni Minghetti、Mario Manassero、Mirella Sansoni

  DOI：10.1039/dt9960004217

  日期：——

  The reaction of a series of 6-substituted-2,2'-bipyridines HL (N(2)C(10)H(7)R, R = CH(2)Ph, CHMePh, CMe(2)Ph, CH(2)Me, CMe(3) or CH(2)CMe(3)) with HAuCl4 or Na[AuCl4] has been investigated. Under different experimental conditions, salts [H(2)L][AuCl4], adducts [Au(HL)Cl-3] or cyclometallated derivatives [Au(L)Cl][X] (X = AuCl4, BF4 or PF6) have been isolated. The cyclometallated species arise from direct activation of a C-H bond either of a phenyl or a methyl substituent. The structures of an adduct [AuN2C10H7(CHMePh)-6}Cl-3] and two metallated species [AuN2C10H7(CMe(2)C(6)H(4))-6}Cl][AuCl4] and [AuN2C10H7(CMe(2)CH(2))-6}Cl][BF4] . 0.5H(2)O have been determined by X-ray diffraction. In the adduct the gold atom is bonded to the nitrogen atom of the unsubstituted pyridine ring: a long-range interaction with the other nitrogen atom is observed, Au ... N 2.758(4) Angstrom. In the two cyclometallated species the bipyridines act as tridentate N,N,C anions, giving a [5,6] and a [5,5]-fused ring system, respectively. In [AuN2C10H7(CMe(2)C(6)H4)-6}Cl](+) the hexaatomic N,C ring adopts a boat-like conformation: the structure reveals a rather short interaction between one hydrogen of the Me group in axial position and the gold atom, Au ... H2.62 Angstrom. The pentaatomic N,C ring in [AuN2C10H7(CMe(2)CH(2))-6}Cl](+) is not planar: the co-ordination around the gold atom is essentially square planar. The new cyclometallated complexes [Au(N,N,C)Cl](+) are compared with those derived from similarly substituted pyridines described previously.
• Zucca, Antonio; Stoccoro, Sergio; Cinellu, Maria Agostina, Journal of the Chemical Society, Dalton Transactions, 1999, # 19, p. 3431 - 3438
  作者：Zucca, Antonio、Stoccoro, Sergio、Cinellu, Maria Agostina、Minghetti, Giovanni、Manassero, Mario

  DOI：——

  日期：——
• Regiospecific Acylation of Cycloplatinated Complexes: Scope, Limitations, and Mechanistic Implications
  作者：Jeffrey Carroll、Hannah G. Woolard、Robert Mroz、Charles A. Nason、Shouquan Huo

  DOI：10.1021/acs.organomet.6b00174

  日期：2016.5.9

  A series of platinum complexes based on the tridentate cyclometalating ligand derivatives 6-arylamino-2,2'-bipyridine, 6-phenoxy-2,2'-bipyridine, 6-phenylthio-2,2'-bipyridine, 6-benzyl-2,2'-bipyridine, and 6-benzoyl-2,2'-bipyridine were synthesized, and their acylation reactions were studied. Acylation of platinum complexes based on 6-(4-R-phenylamino)-2,2'-bipyridine derivatives (R = CH3O, CH3, Cl, COOEt) tolerates both electron -donating and electron -withdrawing substituents on the aryl ring that are para to the amino group. However, platinum complexes based on 6-(3-R'-phenylamino)-2,2'-bipyridine (R' = CH3, Cl, Br) did not undergo the acylation reaction under the same conditions. Interestingly, the acylation of the platinum complexes based on 6-(3-fluorophenylamino)-2,2'-bipyridine proceeded smoothly, and the results indicate that the acylation is regiospecific and occurs at the metalated carbon. Complexes based on 6-phenoxy-2,2'-bipyridine, 6-phenylthio-2,2'-bipyridine, and 6-benzyl-2,2'-bipyridine are also regioselectively acylated. A cyclometalated platinum complex based on 6-benzoyl-2,2'-bipyridine, where the benzene is more electron deficient than those in other cyclometalated platinum complexes, failed to undergo the acylation reaction. The acylation can be carried out in acetic acid, 1,2-dichloroethane, benzonitrile, and acetonitrile. Other acyl halides such as benzoyl chloride and crotonyl chloride are also effective acylating reagents. On the basis of the fact that the reaction is discouraged by the electron deficiency of the phenyl ring and contrasting results of the acylation of platinum complexes based on 6-(3-R'-phenylamino)-2,2'-bipyridine (R' = CH3, F, Cl, Br), an unprecedented electrophilic addition platinum migration rearomatization cascade mechanism is proposed for the regiospecific acylation reaction.
• Platinum complexes with NNC ligands. Syntheses, electrochemical and spectroscopic characterisations of platinum(II) and relevant electroreduced species
  作者：Gavino Sanna、Giovanni Minghetti、Antonio Zucca、Maria I. Pilo、Renato Seeber、Franco Laschi

  DOI：10.1016/s0020-1693(00)00136-5

  日期：2000.7

  A series of cyclometallated platinum(II) species with N-N-C ligands (N-N-C = ortho-C-deprotonated form of 6-benzyl-substituted 2,2'-bipyridines) and different fourth monodentate ligands (Cl-, I-, CN-, CO, PPh3, Py, MeCN) has been investigated electrochemically, with particular emphasis to the analysis of the relatively st;able one-electron reduced species. EPR spectra have been recorded at different temperatures on the electroreduced solutions. The :analyses were supported by a systematic comparison with simulated spectra and allowed a definition of the interaction of the additional unpaired electron with the Pt-195, N-14, and H-1 nuclei present in the molecule. Attention has been also paid to the effects of the ligands on the thermodynamics (E-1/2,E-r) of the reduction, as well as to some reactivity aspects of the substrates that could be shown by voltammetric tests. A number of these compounds have been synthesised for the first time, so that a full characterisation has been performed. (C) 2000 Elsevier Science S.A. All rights reserved.