Optically induced carbazolyl containing polyethers: Concentration effects

Pisarski, Wojciech A.; Swinarew, Andrzej; Czaja, M.; Piekarnik, Beata; Grobelny, Zbigniew; Getautis, Vytautas; Gražulevičius, Juozas V.; Niedziela, Tomasz; Trzebicka, Barbara; Stolarzewicz, Andrzej

doi:10.1016/j.molstruc.2008.02.042

Cited by 9 publications

(4 citation statements)

References 20 publications

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“…The methacrylate-based Polymethacrylates with anthryl and carbazolyl groups D Neugebauer et al copolymers with carbazolyl groups had blue-violet fluorescence at 344, 361 and 382 nm, which was observed previously for carbazolylcontaining polyethers prepared by anionic polymerization (352, 368 and 390 nm). 30 In addition, fluorescence maxima at similar wavelengths (348 and 368 nm using l exc ¼295 nm) were present for the copolymers of CMA and methacrylic acid synthesized by uncontrolled FRP. 25 For anthryl copolymers, light emission was shifted into longer wavelengths in the blue-green range (390, 412 and 438 nm), in agreement with the fluorescence results obtained for AMA/MMA copolymers prepared by FRP (maxima at 390, 413 and 442 nm using l exc ¼350 nm).…”

Section: Luminescence Propertiesmentioning

confidence: 91%

Polymethacrylates with anthryl and carbazolyl groups prepared by atom transfer radical polymerization

Neugebauer

Charasim

Swinarew

et al. 2011

Polym J

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Monomers containing chromophore groups, that is, 9-anthrylmethyl methacrylate (AMA) and 2-(9-carbazolyl)ethyl methacrylate (CMA), were copolymerized with methyl methacrylate (MMA) using atom transfer radical polymerization (ATRP) conditions, resulting in two series of (co)polymers with various amounts of included chromophore units, namely P(MMA-co-AMA) (3-30 mol%) and PAMA and P(MMA-co-CMA) (3-20 mol%). The relative reactivity ratios of both comonomer pairs were determined using the Fineman-Ross method (r MMA ¼1.19, r AMA ¼0.48 and r MMA ¼1.10, r CMA ¼0.77). Glass transition temperatures (T g s) of the polymers increased with the content of chromophore groups. A comparison of luminescence demonstrated more intense light emission by polymethacrylates with carbazolyl groups than by copolymers with anthryl groups. The wavelength of emitted light also differed in the range of blue-violet and blue-green fluorescence for carbazolyl and anthryl copolymers, respectively. Polymer Journal (2011) 43, 448-454; doi:10.1038/pj.2011.10; published online 2 March 2011Keywords: anthracene; ATRP; carbazole; luminescence; polymethacrylates INTRODUCTION Luminescent polymers that have the ability to emit light in response to a stimulus are known as smart polymers. These polymers can be used for fabricating light-emitting diodes, electrophotographic and photorefractive materials, as well as photoluminescent and electroluminescent devices. 1 A proper design of the molecular structure of polymers with luminescence is required to tune the emission color in various regions of the visible spectrum. The parameters responsible for this effect are related to the types of chromophore groups, and their content and density of incorporation in the polymer chain. Particularly, carbazole-and anthracene-based polymers, belonging to a large family of luminescent macromolecules, have found increasing interest because of their numerous industrial applications, such as coatings, inks, adhesives and photolithography, as well as their use in the construction of electrical switching devices. 2 Previously, copolymers containing carbazolyl groups were synthesized using various polymerization methods, such as the cationic photopolymerization of epoxy, 3 oxetane 4 and vinyl ether monomers (2-(9-carbazolyl)ethyl vinyl ether); 5-7 anionic polymerization of oxiranes ([(9-carbazolyl)methyl] or [(9-carbazolyl)ethoxymethyl]oxirane) 8 or methacrylates (2-(N-carbazolyl)ethyl methacrylate) 9 and free radical polymerization (FRP) of vinyl monomers (N-vinylcarbazole), 10,11 including (meth)acrylates. 12,13 The other luminescent copolymers with anthryl substituents were prepared by conventional FRP.

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Section: Luminescence Propertiesmentioning

confidence: 91%

Polymethacrylates with anthryl and carbazolyl groups prepared by atom transfer radical polymerization

Neugebauer

Charasim

Swinarew

et al. 2011

Polym J

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“…The second step was polymerization reaction, where (9-carbazolyl)-methytiirane reacted with oligo(potassium glycidoxide) synthesized in the reaction of glycidol with potassium hydride in the presence of 18-crown-6 in tetrahydrofuran ( Scheme 1 ). The formation of the compound and its luminescent properties are described in detail in the papers [ 24 , 25 , 26 ].…”

Section: Methodsmentioning

confidence: 99%

Luminescent Cellulose Fibers Modified with Poly((9-Carbazolyl)Methylthiirane)

et al. 2020

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This article presents the results of research related to the development of cellulose man-made fibers with luminescent properties. The fibers were obtained from regenerated cellulose with the use of the N-Methylmorpholine-N-Oxide (NMMO) method for lyocell (Tencel) fiber formation. The method is named after the cellulose solvent (NMMO) used to obtain the spinning solution. Fibers are formed by the dry–wet spinning method. Due to the characteristic of the lyocell process, the fibers were easily modified to achieve luminescent properties with star-shaped organic compound poly((9-carbazolyl)methylthiirane) (KMT). Fibers were examined on their mechanical parameters with the use of Zwick Z2.5/TN1S tensile testing machine, and the results show the influence of the KMT concentration in the fiber matrix on mechanical parameters of the fibers. The study also attempted to determine the concentration of the modifier in the fibers with the use of UV-VIS Spectrofluorometer JASCO. The luminescent properties of fibers were estimated as well, using Jobin–Yvon spectrofluorometer FLUOROMAX–4, and the results are very promising as the fibers emit blue light in the range of visible light spectrum even for small concentrations of KMT (about 0.1 wt.%).

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“…Complexing compounds are very popular because of the wide application range. They are used among other things: in medicine as a capture and neutralize metal ions compounds [3,4,5], as catalysts in polymerization reactions [6,7,8,9,10,11,12,13], as crown ether complex cation ionic liquids catalysts [14,15,16], as activators [17,18], as protecting groups in organic synthesis [19], as chiral gels utilized as memory-erasing recycle system or logic gates based on the stimuli-responsive gel–sol transition, as chiral selectors to separate amino acid enantiomers in capillary electrophoresis analysis of amino acid enantiomers [20,21,22,23], as effective sensors [24,25,26,27,28,29], as a component of ion-selective membrane electrode [30,31], as extractants for various elements [32,33,34,35,36], and as hydraphiles—synthetic ionophores designed to mimic some properties of protein channels that conduct cations such as sodium [37].…”

Section: Introductionmentioning

confidence: 99%

New Kind of Polymer Materials Based on Selected Complexing Star-Shaped Polyethers

Swinarew

Swinarew²,

Gabor

et al. 2019

Polymers

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In today’s analytical trends, there is an ever-increasing importance of polymeric materials for low molecular weight compounds including amines and drugs because they can act as carriers or capture amines or drugs. The use of this type of materials will allow the development of modern materials for the chromatographic column beds and the substrates of selective sensors. Moreover, these kinds of materials could be used as a drug carrier. Therefore, the aim of this study is presenting the synthesis and complexing properties of star-shaped oxiranes as a new sensor for the selective complexation of low molecular weight compounds. Propylene oxide and selected oxirane monomers with carbazolyl in the substituent were selected as the monomers in this case and tetrahydrofuran as its solvent. The obtained polymer structures were characterized using the MALDI-TOF. It was found that in the initiation step potassium hydride deprotonates the monomer molecule and takes also part in the nucleophilic substitution. The resulting polymeric material preferably cross-linked with selected di-oxiranes (1,2,7,8-diepoksyoktan in respect ratio 3:1 according to active center) was then used as a stationary phase in the column and thin layer chromatography for amine separation and identification. Sorption ability of the resulting deposits was determined using a quartz microbalance (QCMB). The study was carried out in stationary mode and flow cells to simulate actual operating phase conditions. Based on changes in electrode vibration frequency, the maximum amount of adsorbed analyte and the best conditions for its sorption were determined.

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Optically induced carbazolyl containing polyethers: Concentration effects

Cited by 9 publications

References 20 publications

Polymethacrylates with anthryl and carbazolyl groups prepared by atom transfer radical polymerization

Polymethacrylates with anthryl and carbazolyl groups prepared by atom transfer radical polymerization

Luminescent Cellulose Fibers Modified with Poly((9-Carbazolyl)Methylthiirane)

New Kind of Polymer Materials Based on Selected Complexing Star-Shaped Polyethers

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