Synthesis of new copper(<scp>i</scp>) based linear 1-D-coordination polymers with neutral imidazolinium-dithiocarboxylate ligands

Neuba, Adam; Ortmeyer, Jochen; Konieczna, Dagny Dagmara; Weigel, Guenter; Flörke, Ülrich; Henkel, Gerald; Wilhelm, René

doi:10.1039/c4ra09033k

Cited by 21 publications

(23 citation statements)

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“…The starting point for the preparation of [Cu 4 (Bz 2 ImCS 2 ) 4 Cl 2 ] 2+ ( 2 ) and [Cu 3 (Bz 2 ImCS 2 ) 5 ] 3+ ( 3 ) was the coordination polymer [CuCl(Bz 2 ImCS 2 ) 2 ] n ( 1 ), which is easily accessible in excellent yields and purity by reaction of CuCl with Bz 2 ImCS 2 in acetonitrile (Scheme ), as a solid with low solubility. A combined NMR spectroscopy and ESI‐MS study showed us that liquid phases obtained, after saturating MeCN with 1 and subsequent filtering, contain the mononuclear ions [Cu(Bz 2 ImCS 2 ) 2 ] + and [CuCl 2 ] – as the only copper‐containing species in solution.…”

Section: Resultsmentioning

confidence: 99%

“…The compound 1,3‐dibenzyl‐3‐imidazolinium‐2‐dithiocarboxylate (Bn 2 ImCS 2 ) was prepared according to the literature . The synthesis of the coordination polymer [CuCl(Bz 2 ImCS 2 )] n ( 1 ) was recently reported …”

Section: Methodsmentioning

confidence: 99%

“…[44] The synthesis of the coordination polymer [CuCl(Bz 2 ImCS 2 )] n (1) was recently reported. [33] Physical Measurements: Spectra were recorded with the following devices: UV/Vis: Varian Cary 50 spectrophotometer; and IR: Bruker Vertex 70 spectrometer. MS-ESI measurements were performed with a Waters SYNAPT G2 oa-QToF mass spectrometer equipped with a standard ESI source.…”

Section: Methodsmentioning

confidence: 99%

“…[31a,31b,32] To fill this "knowledge gap", we described recently the first imidazolinium-dithiocarboxylate copper complexes, [CuX-(Bz 2 ImCS 2 )] n [X = Cl (1), Br; Bz 2 ImCS 2 = 1,3-dibenzylimidazolium-2-dithiocarboxylate, Scheme 1], and investigated the photocatalytic properties of these new materials. [33] The compounds [CuX(Bz 2 ImCS 2 )] n [X = Cl (1), Br] are coordination polymers in which single 1D-chains are formed by alternately arranged {CuX} units and betaine ligands. At that time, attempts to synthesize discrete mono-or polynuclear copper complexes with Bz 2 ImCS 2 ligands failed.…”

Section: Introductionmentioning

confidence: 99%

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A Sophisticated Approach towards a New Class of Copper(I)–Sulfur Cluster Complexes with Imidazolinium–Dithiocarboxylate Ligands

et al. 2017

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As a contribution to a better understanding of the coordination properties of imidazolinium–dithiocarboxylate ligands towards copper, the first route towards oligonuclear copper–betaine complexes has been developed. Treatment of the coordination polymer [CuCl(Bz2ImCS2)]n (1) suspended in acetonitrile with thallium(I) hexafluorophosphate in different ratios affords the discrete copper(I) cluster cations [Cu4(Bz2ImCS2)4Cl2]2+ (2) and [Cu3(Bz2ImCS2)5]3+ (3). Single‐crystal X‐ray diffraction of 2(PF6)2·2MeCN and 3(PF6)3·2MeCN·Et2O reveals the occurrence of unique copper–sulfur architectures. The Cu–S/Cl skeleton of 2 contains two elongated trigonal‐prismatic {Cu4S2} entities which share a common {Cu4} face. In contrast, the Cu atoms of 3 define an isosceles triangle. Both compounds exhibit distorted tetrahedral copper coordination sites, based on S3Cl (within 2) and S4 (within 3) donor sets, and host dithiocarboxylate zwitterions in each of two different coordination modes. Overall, three different types of binding principles towards copper are presented here.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A Sophisticated Approach towards a New Class of Copper(I)–Sulfur Cluster Complexes with Imidazolinium–Dithiocarboxylate Ligands

et al. 2017

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“…To verify whether the styryl group attached on poly(l-cysteine) can carry out the free radical polymerization and thiol-ene click reaction that are suitable methods to form a polypeptide networked polymers, [31][32][33][34] we first examined free radical polymerization to obtain a polypeptide network using the lowest molecular weight of PCys(VBn) ((M n : 1130, M w /M n = 1.20) in the presence of AIBN as a radical source (Scheme 4). After heating them in a nitrogen atmosphere for 24 h, an easily breakable and totally insoluble glassy solid polymer (Network-PCS) was obtained in high yield (90%), and their film formation was not observed.…”

Section: Resultsmentioning

confidence: 99%

Phosgene‐Free Synthesis of Poly(l‐cysteine) Containing Styrene Moiety as a Reactive Function

Akbulut

Yamada

Endō

2017

Macro Chemistry & Physics

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for extreme impurity-free conditions to achieve the polymerization without side reactions, the sensitive nature of NCA for heating, and moisture are major drawbacks of its production toward practical use and chemical modifications. Thus, research on the development of alternative procedures [16][17][18][19][20][21][22] to obtain polypeptides from nontoxic materials with high purity and stability through the development of new synthetic strategies is of great interest in this research area.Quite recently, we have developed a newly synthetic route for the production of NCAs and polypeptides where the intramolecular cyclization of activated urethane derivatives of α-amino acids followed by the ring-opening polymerization of the in situ formed NCA led to the production of polypeptides without the use and production of any toxic compounds. [23][24][25] In this synthetic method, these activated urethane derivatives were readily synthesized by a twostep procedure: (i) the transformation of α-amino acids into the corresponding ammonium salts and (ii) the smooth reaction of N-carbamylation of the salts with diphenyl carbonate (DPC) to afford the corresponding urethane compound. Therefore, polypeptides synthesis using the urethane derivative, which are stable for moisture or heating and available for storing several months at room temperature, is more feasible than traditional ring opening polymerization of highly reactive NCAs in aspect of potential applicability for the convenient preparation of various kinds of functional polypeptides.The side-chain modification of polypeptides is an important tool for creating therapeutic conjugates, generating novel protein constructs and probing natural systems. Research on the combination of some reactive groups with amino acids and the discovery of different initiator systems for NCA-based peptide synthesis have emerged as one of the most popular topics in the synthesis of unique macromolecular architectures in recent years. [26][27][28] However, the sensitive nature of NCAs derivatives only allows two fundamental routes for the preparation of sidechain-modified polypeptides: (i) the prepolymerization modification route where the modified amino acid can be converted to NCA derivatives and then polymerized and (ii) the postpolymerization modification route where a chemically reactive moiety bearing polypeptide on the side chain can react with various functional reagents. [24,29] Polypeptides A novel approach toward the synthesis of N-carboxyanhydride precursor available for postpolymerization modification has been developed through a phosgene-free method offering a safer and green way to obtain peptide monomers under exceptionally mild reaction conditions. The homo and co-polypeptide bearing a reactive styrene moiety are prepared through the polycondensation of N-phenoxycarbonyl derivative of 4-vinylbenzyl-l-cysteine (NPC-Cys(VBn)) with the elimination of phenol and CO 2 while varying the feed ratio to the primary amine initiator to give the corresponding polypeptides without any d...

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CuI‐catalyzed tandem synthesis of thioethers using aryl halides, electron‐deficient alkenes, and sodium iso‐propyl xanthogenate

Abbasi

Nowrouzi

Khezri

2020

Applied Organom Chemis

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Synthesis of new copper(i) based linear 1-D-coordination polymers with neutral imidazolinium-dithiocarboxylate ligands

Abstract: An imidazolinium-dithiocarboxylate betaine has been applied for the first time as a ligand in a coordination polymer with copper(i) halides.

Cited by 21 publications

References 86 publications

A Sophisticated Approach towards a New Class of Copper(I)–Sulfur Cluster Complexes with Imidazolinium–Dithiocarboxylate Ligands

A Sophisticated Approach towards a New Class of Copper(I)–Sulfur Cluster Complexes with Imidazolinium–Dithiocarboxylate Ligands

Phosgene‐Free Synthesis of Poly(l‐cysteine) Containing Styrene Moiety as a Reactive Function

CuI‐catalyzed tandem synthesis of thioethers using aryl halides, electron‐deficient alkenes, and sodium iso‐propyl xanthogenate

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