33795-37-8

Usage

Uses

Used in Coordination Chemistry:
1,10-Phenanthroline-2-carbaldehyde is used as a ligand for forming complexes with metal ions, particularly transition metals, in coordination chemistry. The presence of nitrogen and oxygen atoms in its structure allows it to chelate metal ions, resulting in stable complexes with potential applications in various fields.
Used in Catalysis:
The metal complexes formed by 1,10-phenanthroline-2-carbaldehyde have been found to have potential applications in catalysis. The ligand's ability to coordinate with metal ions can enhance the catalytic activity and selectivity of the resulting complexes, making them useful in various chemical reactions.
Used in Medicinal Chemistry:
1,10-Phenanthroline-2-carbaldehyde and its metal complexes have potential applications in medicinal chemistry. The unique properties of these complexes, such as their redox activity and ability to interact with biological molecules, make them promising candidates for the development of new drugs and therapeutic agents.
Used in Materials Science:
The metal complexes of 1,10-phenanthroline-2-carbaldehyde also have potential applications in materials science. Their unique electronic, optical, and magnetic properties can be exploited to develop new materials with specific functionalities, such as sensors, catalysts, and electronic devices.
Used in Organic Synthesis:
1,10-Phenanthroline-2-carbaldehyde is used as a building block in organic synthesis for the preparation of different functionalized compounds. Its aldehyde group can be readily modified through various chemical reactions, allowing the synthesis of a wide range of organic compounds with diverse properties and applications.

InChI:InChI=1S/C13H8N2O/c16-8-11-6-5-10-4-3-9-2-1-7-14-12(9)13(10)15-11/h1-8H

Upstream product

• 37067-10-0 2-hydroxymethyl-1,10-phenanthroline 
• 3002-77-5 2-methyl-1,10-phenanthroline 
• 66-71-7 1,10-Phenanthroline 
• 75-24-1 trimethylaluminum 
• 1082-19-5 1,10-phenanthroline-2-carbonitrile 
• 37067-12-2 methyl 1,10-phenanthroline-2-carboxylate 

Downstream Products

• 876126-86-2 2-formyl-1,10-phenanthroline(2,6-diethylanil) 
• 876127-06-9 [(2-formyl-1,10-phenanthroline 2,6-diethylanil)]FeCl₂ 
• 57154-80-0 1,10-phenanthroline-2-carboxylic acid chloride 
• 1891-17-4 1,10-phenanthroline-2-carboxylic acid 
• 37067-10-0 2-hydroxymethyl-1,10-phenanthroline 

Relevant academic research and scientific papers

A self-folding metallocavitand

The synthesis and characterization of novel metallocavitand 6 are described. This is a covalent hybrid of a deepened, self-folding cavity and a Zn-phenanthroline fragment. Host 6 features a large molecular cavity of -8×10 A dimensions, and the metal binding site is directed in toward the cavity. Binding abilities of the metallocavitand in solution was demonstrated for quinuclidine 11 and Dabco 12 using UV-vis and 1H NMR spectroscopy. Intramolecular hydrogen bonds at the upper rims of cavitand 6 resist the unfolding of the inner cavities and thereby increase the energetic barrier to guest exchange. The exchange is slow on the NMR time scale (at ambient temperatures, CD2Cl2), and kinetically stable complexes result. Both the polyaromatic cavity and metallosite participate simultaneously in the binding event. Zinc-containing deep cavities may be attractive as catalytic chambers for hydrolysis and esterification.

Synthesis of Metal-Containing Poly(thiophene methines) via Solid-and Melt-State Polymerization and Their Related Applications as Highly Sensitive Ni2+ Chemosensors

Metal-containing polymers have attracted continuous interest, for they combine the features of a metal complex and a polymer. Here, a series of thiophene methine based phenanthroline ligands (L1-L4) and their metal (Zn(II) and Cd(II)) complexes were prepared as monomers. Accordingly, metal-containing poly(thiophene methines) were prepared from these metal complexes via solid-and melt-state polymerization (S(M)SP). The polymerization process was preliminarily investigated by a crystal structure study, NMR analysis, and absorbance spectra. Furthermore, the metal-free polymer (PL4) prepared directly from the ligand via MSP was tested as a metal ion chemosensor, which showed good selectivity and excellent sensitivity toward Ni2+ with a detection limit of 4.1 × 10-9 M.

N ortho acyl substituted nitrogen-containing heterocyclic compound and process for preparing aminal iron (II) complexes thereof

Provided are a process for preparing an N ortho acyl substituted nitrogen-containing heterocyclic compound and an aminal iron (II) complex thereof, and the use of the complexes obtained by the process in an olefin oligomerization catalyst. The N ortho acyl substituted nitrogen-containing heterocyclic compound in the present invention is for example 2-acyl-1,10-phenanthroline or 2,6-diacetyl pyridine as shown in formula b, and the N ortho acyl substituted nitrogen-containing heterocyclic compound in the present invention is produced by a reaction of a precursor thereof in a substituted or unsubstituted nitrobenzene. Preferably the precursor shown in formula I in the present invention is produced by 1,10-phenanthroline reacting with trialkyl aluminum, or a halogenoalkyl aluminum RnAIXm, or a substituted or unsubstituted benzyl lithium Ph′CH2Li, followed by hydrolysis. The preparation method provided in the present invention has a few synthetic steps, an easy process, a low toxic effect, and reduces the preparation costs of the catalyst, and has a promising outlook in the industrial application.

1H NMR spectroscopic elucidation in solution of the kinetics and thermodynamics of spin crossover for an exceptionally robust Fe2+ complex

A series of Fe2+ spin crossover (SCO) complexes [Fe(5/6)]2+ employing hexadentate ligands (5/6) with cis/trans-1,2-diamino cyclohexanes (4) as central building blocks were synthesised. The ligands were obtained by reductive amination of 4 with 2,2′-bipyridyl-6-carbaldehyde or 1,10-phenanthroline-2-carbaldehyde 3. The chelating effect and the rigid structure of the ligands 5/6 lead to exceptionally robust Fe2+ and Zn2+ complexes conserving their structure even in coordinating solvents like dmso at high temperatures. Their solution behavior was investigated using variable temperature (VT) 1H NMR spectroscopy and VT Vis spectroscopy. SCO behavior was found for all Fe2+ complexes in this series centred around and far above room temperature. For the first time we have demonstrated that the thermodynamics as well as kinetics for SCO can be deduced by using VT 1H NMR spectroscopy. An alternative scheme using a linear correction term C1 to model chemical shifts for Fe2+ SCO complexes is presented. The rate constant for the SCO of [Fe(rac-trans-5)]2+ obtained by VT 1H NMR was validated by Laser Flash Photolysis (LFP), with excellent agreement (1/(kHL + kLH) = 33.7/35.8 ns for NMR/LFP). The solvent dependence of the transition temperature T1/2 and the solvatochromism of complex [Fe(rac-trans-5)]2+ were ascribed to hydrogen bond formation of the secondary amine to the solvent. Enantiomerically pure complexes can be prepared starting with R,R- or S,S-1,2-diaminocyclohexane (R,R-trans-4 or S,S-trans-4). The high robustness of the complexes reduces a possible ligand scrambling and allows preparation of quasiracemic crystals of [Zn(R,R-5)][Fe(S,S-5)](ClO4)4·(CH3CN) composed of a 1:1 mixture of the Zn and Fe complexes with inverse chirality.

Solvent extraction of americium(iii) and europium(iii) with tridentate N,N-dialkyl-1,10-phenanthroline-2-amide-derived ligands: extraction, complexation and theoretical study

The extraction and complexation behavior of soft-hard combined N,N-dialkyl-1,10-phenanthroline-2-amide (PTA) ligands with Am(iii) and Eu(iii) in HNO3 solution was investigated. The effects of acidity of the aqueous solution, shaking time, concentration of the extractant and temperature on the distribution ratios were studied. The extraction ability for both Am(iii) and Eu(iii) was found to decrease with an increase in the length of the substituent alkyl chains, and the highest extractability and selectivity for Am(iii) over Eu(iii) were found for the diethyl-substituted ligand. The separation factor for Am(iii) over Eu(iii) reached around 7.6 at low acidity and high salinity. UV-vis titrations revealed that the dialkyl-substituted tridentate PTAs all predominantly formed 1?:?1 complexes with Eu(iii), which agreed well with the results of slope analyses in the extraction experiments. The stability constants (KEuL) as well as the protonation constants (KH) were also determined by UV-vis titration. Computational chemistry gave a good explanation of the relationship between the alkalinity and the protonation energy of the proposed PTA ligands. Density functional theory (DFT) calculations on the optimized structures of Am(iii) and Eu(iii) complexes with C2-PTA showed that the selectivity may originate from differences in the degree of covalency of the bonds between the metal ions and the donor N atoms, which fits well with the experimental results.

One method of oligomerization of ethylene

The invention discloses an ethylene oligomerization method. The oligomerization reaction of ethylene is realized in a reaction system comprising a 2-formyl-1,10-phenanthroline dichloroaniline iron (II) chloride complex main catalyst, an aluminiferous promoter, water and an organic solvent, wherein the organic solvent is alpha-olefin of Cn (n is less than or equal to 10 and n is more than 4). In the formula (I), R1, R2, R3, R4, R5 or R6 is independently selected form hydrogen, C1-C6 alkyl, halogen, C1-C6 alkoxy and nitryl. The method overcomes technical defects, optimizes an oligomerization reaction process, is high in oligomerization activity, enables the ethylene oligomerization reaction process to be fast in initiation, stable in operation, low-toxicity and environment-friendly, is good in catalysis effect, well balances the cost, and is strong in practicability; the cost of the ethylene oligomerization reaction is greatly reduced, the catalysis effect and the production cost are comprehensively taken into consideration, and the industrialized prospect is wide.

2-Oxazoline/benzoxazole-1,10-phenanthrolinylmetal (iron, cobalt or nickel) dichloride: Synthesis, characterization and their catalytic reactivity for the ethylene oligomerization

Series of 2-benzoxazole-1,10-phenanthrolines (L1-L4) and 2-oxazoline-1,10-phenanthrolines (L5-L8) were synthesized and used as tridentate N^N^N ligands in coordinating with metal (nickel, cobalt or iron) chlorides. Their metal complexes, nickel(II) (Ni1-Ni8), cobalt(II) (Co1-Co8) and iron(II) (Fe1-Fe8), were characterized by elemental and IR spectroscopic analyses. The molecular structures of the ligand L2 and the complexes Ni3, Co1, Co3 and Fe2 have been determined by the single-crystal crystallography. The nickel complex Ni3 and iron complex Fe2 display an octahedral geometry, whereas cobalt complex Co1 is with a distorted bipyramidal geometry and Co3 as square pyramidal geometry. At 10 atm ethylene, all the complexes showed good activities in ethylene dimerization upon activation with appropriate aluminum cocatalysts; the nickel complexes gave the activity up to 3.11 × 106 g mol-1(Ni) h-1 upon activation with diethylaluminum chloride (Et2AlCl), meanwhile the cobalt and iron complexes showed activities up to 1.51 × 106 g mol-1(Co) h-1 and 1.89 × 106 g mol-1(Fe) h-1, individually, upon activation with modified methylaluminoxane (MMAO).

Electronically variable imino-phenanthrolinyl-cobalt complexes; synthesis, structures and ethylene oligomerisation studies

The 2-imino-1,10-phenanthroline ligands, 1,10-C12H7N2-2-CR{double bond, long}N(2,6-i-Pr2-4-R1-C6H2) [R = R1 = H (L1); R = H, R1 = Br (L2); R = H, R1 = CN (L3); R = H, R1 = i-Pr (L4); R = Me, R1 = H (L5); R = Me, R1 = i-Pr (L6)], have been prepared in high yield from the condensation reaction of 1,10-C12H7N2-2-CR{double bond, long}O (R = H, Me) with one equivalent of the corresponding 4-substituted 2,6-diisopropylaniline. The molecular structures of L2, L5 and L6 reveal the imino nitrogen atoms to adopt a transoid configuration with respect to the phenanthrolinyl nitrogen atoms. Treatment of Lx with one equivalent of CoCl2 in n-BuOH at 90 °C gives the high spin complexes, (Lx)CoCl2 [Lx = L1 (1a), L2 (1b), L3 (1c), L4 (1d), L5 (1e), L6 (1f)], in which the metal centres exhibit distorted square pyramidal geometries. Activation of 1a-1f with excess methylaluminoxane (MAO) gives catalysts that are modestly active for the oligomerisation of ethylene affording mainly linear α-olefins along with some degree of internal olefins. While the donor capability of the 4-position of the N-aryl group does not appear to affect the activity of the catalyst, it does have an influence on the ratio of α-olefins to internal olefins. Single crystal X-ray diffraction studies have been performed on L2, L5, L6, 1a, 1c and 1f.

Carboxylic and Phosphate Ester Hydrolysis Catalysed by Bivalent Zinc and Coper Metallosurfactants

The synthesis of three new lipophilic ligands are reported: Nα-(1,10-phenanthrolin-2-ylmethyl)-N-τ-dodecylhistamine (1), N-dodecyl-2-aminomethyl-1,10-phenanthroline (2), and Nα-(2-pyridylmethyl)-Nτ-dodecylhistam