Synthesis and electrochemical polymerization of some monomers with Schiff base or vinylene structures and thiophene moieties

Simionescu, C. I.; Cianga, I.; Ivanoiu, Maria; Duca, Al.; Cocârlă, I.; Grigoraş, Mircea

doi:10.1016/s0014-3057(98)00171-2

Cited by 28 publications

(7 citation statements)

References 18 publications

(1 reference statement)

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“…The residue at 700 7 C was 6.49%. These thermal characteristics are comparable with other results obtained for polyazomethines having thiophene moieties [14].…”

Section: Electrochemical Synthesis Of Polyazomethines 319supporting

confidence: 91%

“…The polyazomethines are usually synthesized via the classical condensation of an amine with an aldehyde, which is often a fairly spontaneous reaction [8][9][10][11][12]. Recently, the authors have reported a new method for synthesis of poly(Schiff-bases) by cation-radical polymerization of monomers containing -CH = N-preformed groups and aromatic end groups such as pyrrole, thiophene, or naphthalene [13,14].…”

Section: Introductionmentioning

confidence: 99%

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Electrochemical Synthesis of some Polyazomethines by Organometallic Reductive Catalysis

Conduruta¹,

Cianga²,

Airinei³

et al. 2006

High Performance Polymers

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Three monomers with preformed Schiff base structures and ~nal bromine atoms were synthesized: N, N°-bis(4-bromophenyl)-terephthaldiimine (I), N, N°-bis(4-bromobenzylidene)-benzene-1,4-dia-mine (II) and N-(4-bromobenzylidene)-4°-bromoaniline (III). All these compounds were used to prepare polyazomethines by dehalogenative coupling reactions via organometallic reductive catalysis (Ni0.bipy). The monomers and corresponding polymers were characterized by spectral methods (FT-IR, 1HNMR, UV-Vis) as well as by thermal analysis

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“…The residue at 700 7 C was 6.49%. These thermal characteristics are comparable with other results obtained for polyazomethines having thiophene moieties [14].…”

Section: Electrochemical Synthesis Of Polyazomethines 319supporting

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Electrochemical Synthesis of some Polyazomethines by Organometallic Reductive Catalysis

Conduruta¹,

Cianga²,

Airinei³

et al. 2006

High Performance Polymers

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“…Thus, in this study, we focused on showing the impact of the final EDOT group on OCL properties and investigating the EDOT-PCL capacity of self-assembly in solution and the subsequent morphological transitions that occurred during thin film formation. The solvents used, chloroform (Chl) and acetonitrile (ACN), were deliberately chosen in order to show the significant influence caused by their difference in polarity and because they are commonly used as reaction media for chemical and electrochemical polymerization [ 42 , 43 , 51 ]. An explanation is also given for the transition from colorless to blue color that was observed during the preparation of a concentrated solution of EDOT-PCL in CDCl3.…”

Section: Introductionmentioning

confidence: 99%

3,4-Ethylenedioxythiophene (EDOT) End-Group Functionalized Poly-ε-caprolactone (PCL): Self-Assembly in Organic Solvents and Its Coincidentally Observed Peculiar Behavior in Thin Film and Protonated Media

Bendrea¹,

Cianga²,

Ailiesei³

et al. 2021

Polymers

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End-group functionalization of homopolymers is a valuable way to produce high-fidelity nanostructured and functional soft materials when the structures obtained have the capacity for self-assembly (SA) encoded in their structural details. Herein, an end-functionalized PCL with a π-conjugated EDOT moiety, (EDOT-PCL), designed exclusively from hydrophobic domains, as a functional “hydrophobic amphiphile”, was synthesized in the bulk ROP of ε-caprolactone. The experimental results obtained by spectroscopic methods, including NMR, UV-vis, and fluorescence, using DLS and by AFM, confirm that in solvents with extremely different polarities (chloroform and acetonitrile), EDOT-PCL presents an interaction- and structure-based bias, which is strong and selective enough to exert control over supramolecular packing, both in dispersions and in the film state. This leads to the diversity of SA structures, including spheroidal, straight, and helical rods, as well as orthorhombic single crystals, with solvent-dependent shapes and sizes, confirming that EDOT-PCL behaves as a “block-molecule”. According to the results from AFM imaging, an unexpected transformation of micelle-type nanostructures into single 2D lamellar crystals, through breakout crystallization, took place by simple acetonitrile evaporation during the formation of the film on the mica support at room temperature. Moreover, EDOT-PCL’s propensity for spontaneous oxidant-free oligomerization in acidic media was proposed as a presumptive answer for the unexpected appearance of blue color during its dissolution in CDCl3 at a high concentration. FT-IR, UV-vis, and fluorescence techniques were used to support this claim. Besides being intriguing and unforeseen, the experimental findings concerning EDOT-PCL have raised new and interesting questions that deserve to be addressed in future research.

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“…29,30 Aromatic polyazomethines can be obtained by different chemical procedures: classical polycondensation between aromatic/heterocyclic dialdehydes with aromatic/heterocyclic diamines; [18][19][20][23][24][25] self-polycondensation of an automer; 32 and polymerization of monomers containing preformed azomethine linkages. 22,[29][30][31][32][33][34][35][36] Among these synthetic approaches, the one employing monomers that contain preformed azomethine bonds seems to be more versatile, provided that it permits the introduction in the conjugated main chain of different moieties (e.g. thienyl, pyrrolyl, naphthyl and aryl) or well-defined polymeric side chains in a controlled manner, thus allowing for a fine tuning of the electrical and/or optical properties of the final materials.…”

Section: Introductionmentioning

confidence: 99%

Electroactive and bioactive films of random copolymers containing terthiophene, carboxyl and Schiff base functionalities in the main chain

et al. 2015

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A new bis-thienyl type monomer with preformed azomethine linkages (AzbT) was chemically synthesized and, subsequently, electro-copolymerized with 2,2′:5′,2′′-terthiophene (Th 3 ). AzbT:Th 3 mixtures with different molar ratios (i.e. 50:50, 60:40 and 80:20) were considered, the resulting thin films being made of random insoluble copolymers, P(AzbT-co-Th 3 )s. The content of AzbT in P(AzbT-co-Th 3 )s was found to increase with the AzbT:Th 3 molar ratio in the electropolymerization medium. Furthermore, characterization of the different copolymers suggests the existence of several concomitant processes in the reaction medium. Thus, depending on the composition of the reaction medium, AzbT worked as a co-monomer and/or as a dopant for the growing polymer chains. The morphology of the films evolved from a porous multi-level surface to a more compact and flat globular structure with increasing AzbT content. On the other hand, the electrochemical and optical properties were also

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Synthesis and electrochemical polymerization of some monomers with Schiff base or vinylene structures and thiophene moieties

Cited by 28 publications

References 18 publications

Electrochemical Synthesis of some Polyazomethines by Organometallic Reductive Catalysis

Electrochemical Synthesis of some Polyazomethines by Organometallic Reductive Catalysis

3,4-Ethylenedioxythiophene (EDOT) End-Group Functionalized Poly-ε-caprolactone (PCL): Self-Assembly in Organic Solvents and Its Coincidentally Observed Peculiar Behavior in Thin Film and Protonated Media

Electroactive and bioactive films of random copolymers containing terthiophene, carboxyl and Schiff base functionalities in the main chain

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