Category: 138219-98-4

《Ruthenium Tris(bipyridine)-Centered Linear and Star-Shaped Polystyrenes: Making Atom Transfer Radical Polymerization and Metal Complex Initiators Compatible》 was written by Wu, Xufeng; Collins, James E.; McAlvin, John E.; Cutts, Russell W.; Fraser, Cassandra L.. Electric Literature of C12H10Cl2N2 And the article was included in Macromolecules on April 24 ,2001. The article conveys some information:

The ligand derivative, 4,4′-bis(chloromethyl)-2,2′-bipyridine (bpy(CH2Cl)2), and Ru(II) complexes with 2, 4, or 6 pendant halomethyl groups were employed as initiators in the atom transfer radical polymerization (ATRP) of styrene to produce linear and star polymers with ligands and chromophores at discrete positions in the polymer architectures. With the metalloinitiators, [Ru(bpy)n{bpy(CH2Cl)2}3-n](PF6)2 (n = 0, 1, 2), styrene polymerizations were run in bulk monomer, as well as in the presence of small amounts of anisole (14% volume/volume vs styrene), employing either CuCl/2bpy(C13H27)2 or CuBr/1,1,4,7,10,10-hexamethyltriethylenetetraamine (HMTETA) as the ATRP catalyst. Kinetics experiments were performed to determine the level of mol. weight control that is attainable in these polymerizations With the former catalyst and when anisole is added, reactions exhibited increased control for the metalloinitiators and ligand initiators. Since the dicationic metalloinitiators exhibited limited solubility, which correlated with poor initiation, attempts were made to improve the compatibility of metalloreagents in the nonpolar ATRP medium. Di- and tetrafunctional metalloinitiators modified with alkyl chains, [Ru{bpy(C13H27)2}n{bpy(CH2Cl)2}3-n](PF6)2 (n = 1, 2), displayed improved initiation and mol. weights closer to targeted values. However, attempts to improve the solubility of the homoleptic complex, [Ru{bpy(CH2Cl)2}3](PF6)2 by substituting a BAr’4- counterion for PF6- did not enhance mol. weight control. The use of DMF, a more polar solvent, in place of anisole did increase solubility of the hexafunctional initiator; at low monomer conversion, polydispersities were lower in DMF vs anisole. Polymers were characterized by gel permeation chromatog. (GPC) with refractive index (RI) and multiangle laser light scattering (MALLS) detection, by UV/vis spectroscopy to confirm the covalent attachment of Ru(II) chromophores to polystyrene chains, and by modulated differential scanning calorimetry (MDSC). After reading the article, we found that the author used 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4Electric Literature of C12H10Cl2N2)

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Electric Literature of C12H10Cl2N2The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Computed Properties of C12H10Cl2N2On May 30, 2000, Wu, Xufeng; Fraser, Cassandra L. published an article in Macromolecules. The article was 《Architectural Diversity via Metal Template-Assisted Polymer Synthesis: A Macroligand Chelation Approach to Linear and Star-Shaped Polymeric Ruthenium Tris(bipyridine) Complexes》. The article mentions the following:

Polymeric metal complexes were constructed by combining living polymerization techniques with coordination chem. These metal-centered linear and star-shaped materials combine the film-forming properties of polymers with optical and other features of metal complexes. A metal template approach offers a versatile alternative to the metallo-initiator method previously employed to generate Ru tris(bipyridine)-centered polystyrenes. Specifically, 4,4′-bis(chloromethyl)-2,2′-bipyridine and 4-chloromethyl-2,2′-bipyridine were utilized as initiators for both the bulk and solution polymerization of styrene using atom transfer radical polymerization (ATRP). Narrow dispersity polystyrenes with bipyridine (bpy) binding sites at the end (bpyPS) or center (bpyPS2) of the chains result. These bpyPSn macroligands were chelated to Ru precursor complexes, RuL2Cl2 (L = bpy, phen) or Ru(DMSO)4Cl2, to form complexes with one or three bpyPSn macroligands, resp. Linear polymers, [RuL2(bpyPSn)]2+, with Ru chromophores at the end or center of the chains, and Ru-centered star-shaped polymers, [Ru(bpyPSn)3]2+, with three and six arms were produced. In all cases, dehalogenation with AgPF6 was crucial for efficient macroligand chelation. The relative efficiency of these reactions was estimated by UV/vis spectroscopy. Mol. weight determination by GPC was coupled with in-line diode array UV/vis spectroscopy to confirm the presence of the Ru chromophores in the eluting polymer fractions. The convergent macroligand chelation approach to star-shaped polymeric metal complexes typically works best for polymers of low to moderate mol. weights (<∼65K), with higher mol. weights possible for systems with a single macroligand coordinated. Specific mol. weight thresholds encountered are determined by the number of macroligands, the position of the bpy on the polystyrene chain, and the total number of arms emanating from the metal core. In the part of experimental materials, we found many familiar compounds, such as 4,4'-Bis(chloromethyl)-2,2'-bipyridine(cas: 138219-98-4Computed Properties of C12H10Cl2N2)

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Computed Properties of C12H10Cl2N2 Pyridine has a conjugated system of six π electrons that are delocalized over the ring.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Quality Control of 4,4′-Bis(chloromethyl)-2,2′-bipyridineOn March 1, 2019, Woo, Sung-Jun; Choi, Sunghan; Kim, So-Yoen; Kim, Pil Soo; Jo, Ju Hyoung; Kim, Chul Hoon; Son, Ho-Jin; Pac, Chyongjin; Kang, Sang Ook published an article in ACS Catalysis. The article was 《Highly Selective and Durable Photochemical CO2 Reduction by Molecular Mn(I) Catalyst Fixed on a Particular Dye-Sensitized TiO2 Platformã€? The article mentions the following:

A new Mn(I)-based hybrid system (OrgD-|TiO2|-MnP) for photocatalytic CO2 reduction is designed to be a co-assembly of Mn(4,4′-Y2-bpy)(CO)3Cl (MnP; Y = CH2PO(OH)2) and (E)-3-[5-(4-(diphenylamino)phenyl)-2,2′-bithiophen-2′-yl]-2-cyanoacrylicacid(OrgD) on TiO2 semiconductor particles. The OrgD-|TiO2|-MnP hybrid reveals persistent photocatalytic behavior, giving high turnover numbers and excellent product selectivity (HCOO- vs. CO) that surpass the catalytic activities of the related homogeneous and other heterogenized Mn photocatalytic systems reported so far. As a typical run, visible-light irradiation of the hybrid catalyst in the presence of 0.1M electron donor (ED) and 0.001M LiClO4 persistently produced HCOO- with a >99% selectivity accompanied by a trace amount of CO; the turnover number (TONformate) reached âˆ?10 after 25 h irradiation The product selectivity (HCOO-/CO) is controlled by changing the loading amount of MnP on the TiO2 surface. In-situ FTIR anal. of the hybrid during photocatalysis revealed that at low Mn concentration, the Mn-H monomeric mechanism associated with HCOO- formation is dominant, whereas at high Mn concentration, CO is formed via an Mn-Mn dimer mechanism. In the part of experimental materials, we found many familiar compounds, such as 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4Quality Control of 4,4′-Bis(chloromethyl)-2,2′-bipyridine)

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Quality Control of 4,4′-Bis(chloromethyl)-2,2′-bipyridine Pyridine has a conjugated system of six π electrons that are delocalized over the ring.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Product Details of 138219-98-4On March 25, 2003, Peter, Katja; Thelakkat, Mukundan published an article in Macromolecules. The article was 《Synthesis and Characterization of Bifunctional Polymers Carrying Tris(bipyridyl)ruthenium(II) and Triphenylamine Unitsã€? The article mentions the following:

The synthesis, characterization, and properties of a highly soluble bifunctional polymer are described in which a tris(bipyridyl)Ru(II) unit acts as dye and triphenylamine units act as charge transport moieties. First a macro-ligand, a bipyridine carrying two poly(4-bromostyrene) chains, was synthesized by atom transfer radical polymerization (ATRP) of 4-bromostyrene in bulk using CuCl/PMDETA as the catalytic system and bis(chloromethyl) bipyridine as the initiator. The target polymer was then obtained via a polymer amination reaction in which the bromophenyl group was converted into a triphenylamine followed by metalation of the bipyridine unit of the macro-ligand with Ru(II) bis(bipyridine). The reaction conditions of ATRP and polymer amination reaction were optimized, and the degree of conversion for both steps was determined by gas chromatog. (GC) anal. of rest monomer content and elemental anal. of unreacted bromine, resp. The control in mol. weight was achieved maintaining a narrow distribution in the desired low mol. weight range of bulk polymerization of 4-bromostyrene. The polymer amination reaction using the Pd(OAc)2 and P(t-Bu)3 system was efficient, and the reaction was complete within 2 h. The metalation reaction could be followed by UV/vis spectroscopy. MALDI-TOF MS of the three polymers was carried out to obtain absolute mol. weights and their distribution. A comparison of these mol. weights gave addnl. information about the degree of polymer amination and metalation reaction. The thermal properties of the different polymers suggest that the thermal stability and the glass transition temperature increases from the starting macro-ligand which carries poly(4-bromostyrene) chains to the intermediate polymer having poly(vinyltriphenylamine) chains and finally to the bifunctional Ru(II) polymer complex. The results came from multiple reactions, including the reaction of 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4Product Details of 138219-98-4)

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals. Product Details of 138219-98-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Smith, Adam P.; Fraser, Cassandra L. published an article on January 29 ,2002. The article was titled 《Metal-Centered Heteroarm Polymers: Chelation of Polystyrene-b-polycaprolactone with a Bipyridine Donor at the Block Junction》, and you may find the article in Macromolecules.Electric Literature of C12H10Cl2N2 The information in the text is summarized as follows:

A dual functional ligand initiator, 4-chloromethyl-4′-hydroxymethyl-2,2′-bipyridine, bpy-(CH2Cl)(CH2OH), was used in a tandem atom transfer radical polymerization-ring-opening polymerization sequence to generate polystyrene-polycaprolactone copolymers with bpy binding sites at the block interface. The coordination of bpy(PS)-(PCl) subunits to Ru, Fe, and Pt centers to form linear and star-shaped structures is described. The results came from multiple reactions, including the reaction of 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4Electric Literature of C12H10Cl2N2)

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals. Electric Literature of C12H10Cl2N2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of C12H10Cl2N2On September 19, 2000 ,《Synthesis of Thermochromic Iron(II) Tris(bipyridine)-Centered Star-Shaped Polyoxazolines and Their Bipyridine-Centered Macroligand Counterparts》 was published in Macromolecules. The article was written by McAlvin, John E.; Scott, Sarah B.; Fraser, Cassandra L.. The article contains the following contents:

Iron tris(bipyridine) complexes [Fe{4,4′-bis(chloromethyl)-2,2′-bipyridine}3], I, and the corresponding iodide analog generated in situ using NaI, II, were used as initiators for the polymerization of a series of 2-R-2-oxazoline monomers (R = Et, EtOX; Me, MeOX; Ph, PhOX; and undecyl, UnOX). The resulting labile core, red-violet Fe-centered star polymers fragment during mol. weight anal. by gel permeation chromatog. (GPC). Thus, samples were subjected to chem. cleavage in aqueous K2CO3 to generate metal-free bipyridine-centered polyoxazolines, bpyPROX2. When combined with ferrous ammonium sulfate, these bpyPROX2 macroligands chelate to Fe(II), regenerating the [Fe(bipyridine)3]2+ chromophores. Both preparative and anal. kinetics experiments generally produce polymers with reasonably narrow mol. weight distribution (∼1.1 – 1.5). Mol. weight vs. percent monomer conversion plots with either the iodide or chloride initiating system were nearly linear for all monomers ; however, only PEOX and PUOX products show good correlation with Mn(calculated) based on monomer/initiator loading. For most monomers, reactions with iodide initiators are faster than the chlorides, and linear first-order kinetics plots were observed Polymerization of oxazolines with 4,4′-bis(halomethyl)-2,2′-bipyridines produced polymers with narrow mol. weight distribution but with mol. weight higher than targeted based on monomer loading. The 1H NMR data indicate that termination with dipropylamine is efficient for EtOX polymerizations Thermal anal. by DSC and TGA reveal few differences between Fe-centered stars and their bpy-centered PROX macroligand counterparts. Variable-temperature UV/vis data of Fe-centered PEOX thin film illustrate the bleaching of the metal to ligand charge transfer band at about 535 nm of an Fe-centered PEOX film heated under N; cooling and reheating revealed that this process is at least partially reversible for all [Fe-(bpyPROX2)3]2+. In the experiment, the researchers used 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4Synthetic Route of C12H10Cl2N2)

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Synthetic Route of C12H10Cl2N2 Pyridine has a conjugated system of six π electrons that are delocalized over the ring.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2002,Organic Syntheses included an article by Smith, Adam P.; Lamba, Jaydeep J. S.; Fraser, Cassandra L.. Application of 138219-98-4. The article was titled 《Efficient synthesis of halomethyl-2,2′-bipyridines: 4,4′-bis(chloromethyl)-2,2′-bipyridine》. The information in the text is summarized as follows:

Silylation of 4,4′-dimethyl-2,2′-bipyridine with LDA followed by chlorotrimethylsilane gave 97% 4,4′-bis(trimethylsilylmethyl)-2,2′-bipyridine, treatment of which with Cl3CCCl3 and CsF in MeCN, gave 91% 4,4′-bis(chloromethyl)-2,2′-bipyridine. Among the 7 other halobipyridines similarly prepared were 98% 5-(chloromethyl)-2,2′-bipyridine 99% 4,4′-bis(bromomethyl)-2,2′-bipyridine. In the experiment, the researchers used 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4Application of 138219-98-4)

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals. Application of 138219-98-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Computed Properties of C12H10Cl2N2On November 24, 2010 ,《Convenient synthesis of functionalized 4,4′-disubstituted-2,2′-bipyridine with extended π-system for dye-sensitized solar cell applications》 appeared in Tetrahedron Letters. The author of the article were Klein, Cedric; Baranoff, Etienne; Nazeeruddin, Khaja Md.; Graetzel, Michael. The article conveys some information:

Exploration of new ruthenium-based sensitizers for dye-sensitized solar cell (DSC) applications required an easy access to multifunctionalized ligands for efficient screening of sensitizers’ properties. Based on the Horner-Wadsworth-Emmons reaction, a convenient synthetic route for the extension of the π-system on 4,4′-disubstituted-2,2′-bipyridines was used to develop a novel series of functionalized 2,2′-bipyridine ligands, e.g., I (R = CO2C6H13, CO2C8C17, OC6H13, OC8H17), with either electron-withdrawing or donating end-capping groups. The experimental part of the paper was very detailed, including the reaction process of 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4Computed Properties of C12H10Cl2N2)

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals. Computed Properties of C12H10Cl2N2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Synthesis of perfluoroalkylated bipyridines – new ligands for oxidation reactions under fluorous triphasic conditions》 was written by Quici, Silvio; Cavazzini, Marco; Ceragioli, Silvia; Montanari, Fernando; Pozzi, Gianluca. Application In Synthesis of 4,4′-Bis(chloromethyl)-2,2′-bipyridine And the article was included in Tetrahedron Letters on April 30 ,1999. The article conveys some information:

Fluorous soluble bipyridines bearing two perfluoroalkylated side chains in the 6,6′- or 4,4′-positions have been prepared in good yields via etherification of 6,6′-bis(chloromethyl)-2,2′-bipyridine or C-alkylation of 4,4′-dimethyl-2,2′-bipyridine. The new ligands L exhibit amphiphilic behavior with respect to certain fluorous-organic biphasic systems. Nevertheless, their ruthenium complexes (RuLn)X generated in situ are efficient catalysts for the epoxidation of trans-stilbene in a fluorous triphasic system CH2Cl2/H2O/C8F18 in the presence of NaIO4. The fluorous phase, where (RuLn)X is trapped, can be used up to four times without major loss of catalytic activity. In addition to this study using 4,4′-Bis(chloromethyl)-2,2′-bipyridine, there are many other studies that have used 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4Application In Synthesis of 4,4′-Bis(chloromethyl)-2,2′-bipyridine) was used in this study.

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Application In Synthesis of 4,4′-Bis(chloromethyl)-2,2′-bipyridine Pyridine has a conjugated system of six π electrons that are delocalized over the ring.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《An improved synthesis of (hydroxymethyl)bipyridines》 was written by Smith, Adam P.; Corbin, Perry S.; Fraser, Cassandra L.. Formula: C12H10Cl2N2 And the article was included in Tetrahedron Letters on April 15 ,2000. The article conveys some information:

Quick and efficient syntheses of 4,4′-bis(hydroxymethyl)-2,2′-bipyridine and 4-(hydroxymethyl)-2,2′-bipyridine are described starting from 4,4′-dimethyl-2,2′-bipyridine and 4-methyl-2,2′-bipyridine, resp., via (trimethylsilyl)methyl-, bromomethyl-, and acetoxymethyl intermediates. After reading the article, we found that the author used 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4Formula: C12H10Cl2N2)

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. Formula: C12H10Cl2N2 Pyridine has a conjugated system of six π electrons that are delocalized over the ring.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem