Synthesis and spectral investigation of alkyl methacrylates with halogenated carbazolyl pendant groups for photonics applications

Bogdał, Dariusz; Yashchuk, Valeriy M.; Pielichowski, Jan; Ogul’chansky, Tymish Yu.; Warzała, M.; Kudrya, Vladislav Yu.

doi:10.1002/app.10469

Cited by 12 publications

(4 citation statements)

References 16 publications

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“…Alkylation of Nucleophiles to Introduce Primary Halide or Alcohol Moieties. To generate ω-chloroalkyl or ω-bromoalkyl derivatives, alkylation of nucleophiles is usually done using α,ω dibromo- or dichloroalkanes, e.g., reaction of 4‘-hydroxy-biphenyl-4-carbonitrile with 1,6-dibromohexane or carbazole with 1,2-dichloroethane . Unfortunately, when using these reagents, bisubstitution is always an issue.…”

Section: Resultsmentioning

confidence: 99%

“…To generate ω-chloroalkyl or ω-bromoalkyl derivatives, alkylation of nucleophiles is usually done using R,ω dibromo-or dichloroalkanes, e.g., reaction of 4′-hydroxy-biphenyl-4-carbonitrile with 1,6-dibromohexane 25 or carbazole with 1,2-dichloroethane. 26 Unfortunately, when using these reagents, bisubstitution is always an issue. In addition, in the case of very basic nucleophiles (e.g., deprotonated carbazole), elimination competes effectively; hence, yields tend to be low and product purification usually requires column chromatography.…”

Section: Resultsmentioning

confidence: 99%

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Facile, Efficient Routes to Diverse Protected Thiols and to Their Deprotection and Addition to Create Functional Polymers by Thiol−Ene Coupling

2008

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Carbazole, dinitrobenzoate, phenol, pyridine, and 4-cyano-4′-alkoxybiphenyl side groups were grafted onto pendant vinyl groups of polybutadiene (PB) by thiol-ene addition to yield functional polymer of polydispersity equal to that of the precursor material. Synthesis protocols that are clean (>90% conversion to desired product) and scalable were developed to incorporate a protected thiol group into functional precursors. The resulting acetyl or benzoyl thioesters are suitable for long-term storage, and are conveniently deprotected and added to polymer in a matter of hours in a straightforward procedure that does not require isolation of the thiol intermediate. Alternatively, PB functionalization could be achieved with equal success by reaction with β-mercaptoethanol (BME), and subsequent esterification of the incorporated hydroxyl groups with a suitable acyl halide. The chemistry described can potentially be applied to add any side group onto any polymer, copolymer, or block copolymer displaying pendant vinyl groups.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Facile, Efficient Routes to Diverse Protected Thiols and to Their Deprotection and Addition to Create Functional Polymers by Thiol−Ene Coupling

2008

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“…Carbazole‐derived monomers and polymers have been extensively studied for their good photoconductive properties 7, 8. Properties of these materials such as good optical photoreactive and charge transporting combined with ease of processing have simulated a tremendous amount of new researches in different areas of material science 9. The synthesis of some carbazole‐containing methacrylate polymers, except the 4‐substitued carbazole methacrylate, and studying of their properties have been reported in some articles 10–12…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and thermal behavior study of methyl methacrylate polymers containing 4‐carbazole substitutes

Babazadeh

2006

J of Applied Polymer Sci

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A new polymerizable monomer, [4-(9-ethyl)carbazolyl]methyl methacrylate (2), was synthesized by reacting of methacrylic acid and 4-hydroxymethyl-9-ethyl carbazole (1) by esterification procedure in the presence of N,N 0 -dicyclohexylcarbodiimide. The resulting monomer was then polymerized free-radically to form the poly (methyl methacrylate) containing 4-(9-ethyl)carbazolyl pendent groups. Also, copolymerization of monomer 2 with various acrylic monomers such as methyl methacrylate, ethyl methacrylate, methyl acrylate, ethyl acrylate, and n-butyl acrylate by azobisisobutyronitrile as a free radical polymerization initiator gave the related copolymers in high yields. The structure of all the resulted compounds was characterized and confirmed by FTIR and 1 H NMR spectroscopic techniques. The average molecular weight of the obtained polymers was determined by gel permeation chromatography using tetrahydrofurane as the solvent. The thermal gravimetric analysis and differential scanning calorimeter instruments were used for studying of thermal properties of polymers. It was found that, with the incorporation of bulky 4-(9-ethyl)carbazolyl substitutes in side chains of methyl methacrylate polymers, thermal stability and glass transition temperature of polymers are increased.

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“…It allows to modify the macromolecules composition without essential influence on macromolecular basic unit energy sites. Such modifications give a possibility to create the model macromolecules for unique photophysical experiments [1,2] and applied problems [3,4]. In this paper the spectral investigation results of two modifications of carbazole-containing macromolecules: pf2-sep (Fig 1,a) and pf2-conj (Fig 1,b) To our opinion, long-wave bands (Fig3, curve2) are connected with impurity molecules which resided after polymer synthesis.…”

Section: Introductionmentioning

confidence: 94%

Spectral properties of carbazole-containing polymers with phosphore groups in the main chain

Bogdał

Yashchuk

Pielichowski

et al. 2002

Selected Papers From the International Conference on Spectroscopy of Molecules and Crystals

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The absorbtion, fluorescence and phosphorescence of the carbazole-containing polymers with phosphore groups in the main chain oftwo types (carbazole chromophores are separated with spacers (pf-sep) and without spacer (pf2-conj)) were studied. It was shown that spectral properties of pf2-sep polymer are connected mainly with optical transitions in individual carbazole chromophores. The optical properties of pf2-conj polymer are rather different comparative the pf2-sep. That, is caused by perturbation carbazole groups electron system by phosphor-groups and influence carbazole groups (belong to the same unit) each other. This perturbation takes place under special relative geometrical displacement of carbazole and phosphor groups.

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Synthesis and spectral investigation of alkyl methacrylates with halogenated carbazolyl pendant groups for photonics applications

Cited by 12 publications

References 16 publications

Facile, Efficient Routes to Diverse Protected Thiols and to Their Deprotection and Addition to Create Functional Polymers by Thiol−Ene Coupling

Facile, Efficient Routes to Diverse Protected Thiols and to Their Deprotection and Addition to Create Functional Polymers by Thiol−Ene Coupling

Synthesis, characterization, and thermal behavior study of methyl methacrylate polymers containing 4‐carbazole substitutes

Spectral properties of carbazole-containing polymers with phosphore groups in the main chain

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