Polychalcones Based on Carbazole-derived Building Blocks: Synthesis by Acetylative Polycondensation

Evsyukov, S. E.; Scherf, Ullrich; Müllen, Kläus

doi:10.1002/(sici)1097-0126(199701)42:1<77::aid-pi661>3.0.co;2-4

Cited by 4 publications

(6 citation statements)

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“…Linear polychalcones reported by Ueda and co‐workers involving A 2 + B 2 approach used methanesulphonic acid and phosphoric acid as solvents and the prepared polymer though thermally stable, was only soluble in sulfuric acid 41 . Evsyukov and co‐workers prepared polychalcones by acetylative polycondensation at high temperature which only resulted in quarternized polychalcone 17 …”

Section: Resultsmentioning

confidence: 99%

“…The biocompatibility and the material versatility imbibed curiosity of many in incorporating this molecule as part of polymer. Chalcones can be integrated into polymers via two approaches, namely, (a) as pendant units, and in most instances are used as photochemical crosslinkers and find application as lithographic material, 14 photo‐resists, 15 placement of mesogens, 13,16 and so forth; (b) chalcones as part of backbone that possess semiconducting properties 17 …”

Section: Introductionmentioning

confidence: 99%

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Polychalcones based on triphenylamine and carbazole building blocks via Claisen–Schmidt route

Jayalakshmi

Keerthika

Santhanagopal

2021

J of Applied Polymer Sci

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Alternating and random copolymers of carbazole and triphenylamine containing polychalcones are prepared by adopting simple Claisen–Schmidt route via A2 + B2 approach. Terephthaldehyde derivative was used as an additional comonomer along with bisaldehyde of triphenylamine to obtain a random copolymer. The prepared polymers are readily soluble in common organic solvents and the polymers exhibited narrow poly dispersity. The polymers are thermally stable and no observable degradation is observed until 350°C. Further, the spin cast thermally annealed films on glass substrate indicated corrugated surface as measured by scanning electron microscope and atomic force microscopy, which could facilitate for greater interaction at the interfaces. Photophysical properties of the polymers in solution and in thin film showed excellent emission characteristics. Both alternating and random copolymers showed a high quantum yield of 0.74 on comparison with quinine sulfate. Polychalcones with triphenylamine/carbazole showed oxidative response in cyclic voltammetry which suggested the suitability as electrochemical sensors and antioxidant coating material.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Polychalcones based on triphenylamine and carbazole building blocks via Claisen–Schmidt route

Jayalakshmi

Keerthika

Santhanagopal

2021

J of Applied Polymer Sci

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“…9-ethyl-3-carbazole and 9-ethyl-3-carbazolecarboxaldehyde were synthesized by a method similar to those reported for carbazole or phenothiazine derivatives. – The UV−vis and PL were measured on UV-3101 PC UV−vis−NIR scanning spectrophotometer and RF-5301 PC spectrofluorophotometer, respectively. All of the measurements were carried out using freshly prepared solutions.…”

Section: Methodsmentioning

confidence: 99%

Aggregation Dependent S1 and S2 Dual Emissions of Thiophene−Acrylonitrile−Carbazole Oligomer

Zhang

Sullivan

Chen

et al. 2008

Crystal Growth & Design

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Dual emissions from S1 (blue region) and S2 (UV region) states of a chromophore with donor−acceptor structure were observed at room temperature. The photophysical properties of the chromophore depend critically on the packing of the molecules. The molecule exhibits weak S1 emission and strong S2 emission; however, when it undergoes solid aggregation, the S1 emission is enhanced while the S2 emission is quenched. The H-packing (face-to-face packing) of the molecules is revealed as the key factor for this interesting aggregation-dependent dual emission.

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“…[26][27][28][29] An increase in the solubility of conjugated polychalcones was facilitated by the introduction of bulky carbazole and triphenylamine fragments, and the resulting polymers were soluble in traditional organic solvents, such as dichloromethane and THF, respectively. 23,24 Therefore, in the present work, 1,1 0 -diacetylferrocene was used as a monomer capable of introducing bulky blocks into the chain of conjugated polychalcones via the Claisen-Schmidt reaction, which according to our previous research made it possible to synthesize polymers soluble in N-methyl-2-pyrrolidone. 30 Although a number of works are devoted to the preparation and determination of the properties of low-molecular ferrocenylenones, [31][32][33][34] the synthesis of high-molecular-weight ferrocene-containing chalcones remains the subject of sporadic research.…”

Section: Introductionmentioning

confidence: 98%

“…17,18,20,21 The thermal polymerization of dibenzoxazines containing a chalcone fragment also leads to the formation of polymer networks. 22 The polychalcones containing a chalcone fragment in the main chain (conjugated polychalcones) have emissive and semiconducting properties and are also of interest as oxidizing agents for the creation of chemical sensors 23,24 and intermediates in the synthesis of heterocyclic polyconjugated systems. 25 At the same time, the use of conjugated polychalcones is limited by their low solubility in most cases.…”

Section: Introductionmentioning

confidence: 99%

Chain branching during the polycondensation of isophthalic aldehyde and 1,1′‐diacetylferrocene by the Claisen–Schmidt reaction

Dvorikova,

Khrustalev,

Ionova

et al. 2024

Journal of Polymer Science

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N‐methyl‐2‐pyrrolidone‐soluble ferrocene‐containing polychalcones, which are promising as a platform for the formation of ferromagnetic coatings after pyrolysis in an inert atmosphere is synthesized through the polycondensation of isophthalic aldehyde and 1,1′‐diacetylferrocene by the Claisen–Schmidt reaction. The structure and the molecular weight distribution of the polychalcones is characterized by NMR, IR spectroscopy, and size exclusion chromatography. It is shown that the formation of polychalcones is accompanied by chain branching via the Michael reactions and the aldol‐croton condensation. The structure of the linear fragments of the polychalcone chains is simulated with a tailored low‐molecular model compound, that is 1,3‐bis(3‐ferrocenyl‐1‐propen‐2‐one)benzene, which is characterized by the NMR and IR spectroscopy as well as the X‐ray diffraction analysis. The obtained results indicate an increasing tendency for polychalcone chain branching with the temperature growth during the Claisen–Schmidt reaction. The weight loss and the increase in magnetization under the conditions of pyrolysis of polychalcones at different temperatures is studied. The assumptions regarding the possible mechanisms of thermal destruction of ferrocene‐containing macromolecules are put forward.

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Polychalcones Based on Carbazole-derived Building Blocks: Synthesis by Acetylative Polycondensation

Cited by 4 publications

References 6 publications

Polychalcones based on triphenylamine and carbazole building blocks via Claisen–Schmidt route

Polychalcones based on triphenylamine and carbazole building blocks via Claisen–Schmidt route

Aggregation Dependent S1 and S2 Dual Emissions of Thiophene−Acrylonitrile−Carbazole Oligomer

Chain branching during the polycondensation of isophthalic aldehyde and 1,1′‐diacetylferrocene by the Claisen–Schmidt reaction

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