Synthesis and Characterization of Triazole Containing Liquid Crystalline Polymers Through 1,3-Dipolar Cycloaddition Polymerization

Devamani,; Srividhya,; Sundaram, Hari; Manjunathan,; Sivashankaran,; Nithyanandan,; Subramanan,; Balamurugan,; Sengodan,; Senthil,

doi:10.1142/s0256767909004473

Cited by 7 publications

(3 citation statements)

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“…There are rather limited publications on the application of CuAAC in SGP for constructing either AB or AA-BB type polymeric backbones: Díaz et al reported about the synthesis of new adhesive polymers with N-arylsulfonamide moieties in the backbones [19]; Van Steenis et al obtained novel conjugated aromatic polymers with molecular weights (MWs) of 60-396 kDa ( 푊 ) by click SGP indicating that this reaction is suitable for constructing long-chain macromolecules with proper material properties [20]; AA-BB type aromatic polyethers having M 푊 of 27.0-32.8 kDa obtained by click chemistry were also reported [21]; liquid crystalline aromatic polyesters (PEs) [22], aliphatic polyethers constituting triethylene glycol [23], multifunctional poly(ethylene glycol)s (PEGs) [24], poly(alkyl aryl ether)s [25], poly(glycoamidoamine)s [26], linear polytriazoles composed of various 1,4:3,6-dianhydrohexitols [27], polytriazoles [28][29][30], and poly(aroyltriazole)s [31] were synthesized via CuAAC SGP as well. Triazole polymers (mostly polyethers on the basis of commercial polyols) were also synthesized under neat conditions, by azide-alkyne cycloaddition SGP at r.t. during 144 h without using metal catalyst [32].…”

Section: Introductionmentioning

confidence: 99%

New 1,2,3-Triazole Containing PolyestersviaClick Step-Growth Polymerization and Nanoparticles Made of Them

Kantaria

Titvinidze

et al. 2018

International Journal of Polymer Science

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High-molecular-weight AA-BB-type aliphatic polyesters were synthesized via Cu(I)-catalyzed click step-growth polymerization (SGP) following a new synthetic strategy. The synthesis was performed between diyne and diazide monomers in an organic solvent as one pot process using three components and two stages. The dipropargyl esters of dicarboxylic acids (component 1) were used as diyne monomers, di-(bromoacetic acid)-alkylene diesters (component 2) were used as precursors of diazide monomers, and sodium azide (component 3) was used for generating diazide monomers. The SGP was carried out in two steps: at Step 1 dibromoacetates interacted with two moles of sodium azide resulting in diazide monomers which interacted in situ with diyne monomers atStep 2 in the presence of Cu(I) catalyst. A systematic study was done for optimizing the multiparameter click SGP in terms of the solvent, duration of both Step 1 and Step 2, solution concentration, catalyst concentration, catalyst and catalyst activator (ligand) nature, catalyst/ligand mole ratio, and temperature of both steps of the click SGP. As a result, high-molecular-weight ( 푊 up to 74 kDa) elastic film-forming click polyesters were obtained. The new polymers were found suitable for fabricating biodegradable nanoparticles, which are promising as drug delivery containers in nanotherapy.

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Section: Introductionmentioning

confidence: 99%

New 1,2,3-Triazole Containing PolyestersviaClick Step-Growth Polymerization and Nanoparticles Made of Them

Kantaria

Titvinidze

et al. 2018

International Journal of Polymer Science

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“…In this regard, this article deals with a series of mesogens possessing 1,4-disubstituted- [ 4-(dimethyl amino)pyridine(DMAP) and hydrated hydrazine are used as received. By the simple SN2 mechanism the 1-bromohexane is prepared from hydrobromic acid and 1-hexanol using benzene as per reported procedure 28 .…”

Section: Introductionmentioning

confidence: 99%

Click Reaction Assisted Synthesis of Heterocyclic Liquid Crystals and Its Characterization

2017

Rasayan J Chem

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The synthesis of 1,4-disubstituted-[1,2,3]-triazoles involving the addition of aryl azide to terminal acetylenes and ethyl acetoacetate are employed in the preparation of a series of non-linear mesogens having ester and imine as linking units. The structures of final compounds and their intermediates are characterized by FTIR, 1 HNMR and 13 CNMR spectroscopy. Optical microscopy and differential scanning calorimetry confirm structural information of liquid crystal phases of mesogens. The final compounds reveal preferentially well-defined threaded nematic phases. In addition, they show weak fluorescence in solution with poor quantum yields and a Stokes shift of around 70 nm.

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“…10 The 1,2,3-triazole rings 45 that result from the CuAAC may also benefit self-organization and electronic properties of the generated adducts due to their strong dipole and aromatic character. Both, calamitic, [11][12][13] polymeric, 14 and discotic [15][16][17] liquid crystals containing the 1,2,3triazole motive have recently been reported. 50 Surprisingly, neither CuAAC nor thermally activated AAC have been employed for the cross-linking of Langmuir films and mesophases.…”

Section: Introductionmentioning

confidence: 99%

Cross-linking of discotic tetraazaporphyrin dyes in 2 and 3 dimensions by “click” chemistry

et al. 2013

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An intrinsic shortcoming of self-organizing materials is their susceptibility to structural changes by mechanical forces and exposure to chemicals and radiation. Cross-linking of the molecules in the desired supramolecular structure is a generally applicable pathway to structurally more stable materials but is difficult to apply to self-organizing materials because the introduction of cross-linkable groups affects their self-organization and the process of cross-linking may alter the supramolecular structure of the 10 preceding phase. Reported here are the synthesis, thermal properties, and cross-linking of octaalkylthio substituted tetraazaporphyrins that contain either eight terminal azide groups or eight terminal acetylene groups. Synthesis of these compounds requires the preparation of the azide and alkyne containing sidechains and their reaction with 1,2-dicyanoethylene-1,2-dithiolate to the corresponding maleodinitrile intermediates. All maleodinitriles are successfully converted to tetraazaporphyrins by the established Mg 15 templated cyclotetramerization in typical yields of 60-70%. Thermal properties of the metal-free and copper(II) metallated tetraazaporphyrins were studied by thermal gravimetric analysis, polarized optical microscopy, differential scanning calorimetry, and variable temperature powder X-ray diffraction measurements. Azide substituted tetraazaporphyrins with trimethylene and hexamethylene spacers as well as acetylene derivatives with with trimethylene spacers unexpectedly display columnar mesophases over 20 ranges of temperature from 30 ºC to 110 ºC. A thermally activated cross-linking of a hexagonal columnar mesophase by cycloaddition at 65 ºC is demonstrated for a 1:1 mixture of azide and acetylene derivatives. At this temperatures the reaction progresses for up to 48 hours but renders the mesophase insoluble and stable to above 200 ºC. The structure of the mesophase is surprisingly little affected by the cross-coupling process that reaches a conversion of 60% of all azide and acetylene groups based on IR measurements. 25 Conversion of up to 80% of azide and acetylene groups is reached by copper catalysed cross-linking of a 1:1 mixture in solution to generate insoluble polymers. A similar degree of conversion is achieved by copper catalysed cross-linking of a 1:1 mixture as Langmuir film after 3 hours. However, transfer of intact cross-linked Langmuir films onto substrates was not successful.

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Synthesis and Characterization of Triazole Containing Liquid Crystalline Polymers Through 1,3-Dipolar Cycloaddition Polymerization

Cited by 7 publications

References 0 publications

New 1,2,3-Triazole Containing PolyestersviaClick Step-Growth Polymerization and Nanoparticles Made of Them

New 1,2,3-Triazole Containing PolyestersviaClick Step-Growth Polymerization and Nanoparticles Made of Them

Click Reaction Assisted Synthesis of Heterocyclic Liquid Crystals and Its Characterization

Cross-linking of discotic tetraazaporphyrin dyes in 2 and 3 dimensions by “click” chemistry

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