Synthesis of Water-Soluble Polyesters Containing Carboxy-Functional Groups in the Polymers Chain and Study of Their Metal Complexes

In the present study, we report the synthesis of a series of anthracene based polyfluorenes containing alkyl substituted 9,10-diphenylanthracene and hydrazone substituted fluorene moieties. The polymers were synthesized via copper catalysed Ullmann coupling, which comparatively is inexpensive as compared to palladium and platinum used in Suzuki coupling. The synthesized polymers were characterized by various spectroscopic techniques. All the polymers exhibited blue emission having band gap in the range of 2.7-2.83 eV. The polymers showed good thermal stability with decomposition temperature over 330 °C and glass transition temperature in the range of 125-140 °C. All the polymers were soluble in common organic solvents with weight average molecular weight in the range of 21,000-25,000. The electrochemical study reveals that the HOMO energy levels of the polymers were in the range of − 5.16 to − 5.26 eV which had elevated compared with that of polyfluorene (5.7 eV). It matched the work function of ITO and ITO/PEDOT: PSS (4.7 and 5.0 eV respectively). These results indicated that the synthesized polymers could be promising materials for applications in light emitting diode.

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“…anthracene Various alkyl substituted 9, 10 DPA were synthesized according to reported methods [43][44][45][46][47][48][49][50][51].…”

Section: Synthesis Of 2-alkyl-910-di (P-methoxyphenyl)mentioning

confidence: 99%

Exploring copper as a catalyst for cost effective synthesis of polyfluorenes: an alternative to platinum and palladium

et al. 2020

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“…A 2-tert butyl-9,10-di (p-methoxyphenyl) anthracene was de-methylated by refluxing it with HBr (48%) in glacial acetic acid for 24 h at 120 °C in an inert nitrogen atmosphere. The crude product was filtered, washed with water to remove acetic acid and recrystallization carried out in ethanol to get crystalline light yellow solid [8,[22][23][24][25][28][29][30][31][32][33]. The yield of the product was 86%.…”

Section: Preparation Of 2-tert Butyl-910-di (P-hydroxyphenyl) Anthramentioning

confidence: 99%

“…Furthermore, due to its high quantum photoluminescent performance due to the orthogonal structure arrangement between phenyl substitutes and anthracene rings, diphenylanthracene is another commonly used moiety in LEPs [24]. Synthesis and sequence analysis of non-symmetric diphenylanthracenes were conducted [25].…”

Section: Introductionmentioning

confidence: 99%

Alkyl and allyl substituted polydibenzofluorene: blue emitters for future display applications

et al. 2020

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5,8-Dibromo-13,13-bis(alkyl)dibenzofluorene derivatives functionalized with different alkyl molecules [M2a-M2f ] and 2-tert butyl-9,10-di (p-hydroxyphenyl) anthracene [M1b], were designed to research the impact of molecular structure on the optical properties of polymer. Polymers were synthesized by aromatic nucleophilic substitution in moderate to strong yields (60-65%). After structural characterization through several techniques (e.g. FTIR, 1 H, and 13 C-NMR), special emphasis was put on the study of their optical properties through UV-Vis and photoluminescence spectroscopy. The polymers demonstrated strong thermal stability up to 350 °C and high glass transition temperature (108-133 °C). All of the polymers showed blue emission within a range of 416-433 nm and had a band gap of 2.87-2.99 eV. The electrochemical study reveals that, HOMO levels for polymers were estimated in the range of − 5.22 to − 5.26 eV and LUMO of − 2.23 to − 2.38 eV. The polymers demonstrated strong thermal stability and blue emission within a range of 416-433 nm. These polymeric materials have demonstrated high photoluminescence which may be useful for future display applications as a good source.

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“…The first category of carboxyl‐containing waterborne polyesters can be dispersed in water after neutralization by amine or alkali, such as a hyperbranched polyester terminated by trimellitic anhydride; the second kind of non‐ionic waterborne polyesters contain polyethylene glycol as the hydrophilic component; and the third type is named as sulfonate‐based waterborne polyesters, which are prepared by introducing sodium isophthalic acid‐5‐sulfonate (SIPA) or sodium dimethyl isophthalate‐5‐sulfonate (SIPM) into the polymer main chains . The last type of polyester contains sulfonate groups and has good water solubility, hygroscopicity, and ionic conductivity because of its ionic group, which has been widely used in chemical fibers, surfactants, coatings, metal complexes, and sizing agents . The molar mass of waterborne polyesters is generally low due to their hydrophilic groups.…”

Section: Introductionmentioning

confidence: 99%

Preparation of waterborne elastic polyesters by chain extension with isophorone diisocyanate as a chain extender

Zheng

Zhu

Cheng

et al. 2019

J of Applied Polymer Sci

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Isophorone diisocyanate was used as a chain extender to coupling the soft segment water-borne polyester with the hard segment water-borne polyester, to overcome the disadvantages of low molar mass and poor mechanical properties of waterborne sulfonatecontaining polyesters. The molecular structure of the extended polyester was confirmed by FTIR and 1 H NMR, and the increased molar mass of the resultant was characterized by SEC. The extended products could be dispersed in water with the emulsion particle size less than 50 nm in diameter, slightly larger than that of precursors of soft-and hard-segment polyesters. The emulsion viscosity of polyesters after the chain extension was lower when the emulsion concentration was not larger than 25 wt%, which is conducive to the spraying application of the polyester for coating. DSC analysis indicated that the polyester after chain extension had two different glass temperatures, suggesting that the polyester bulk had a microphase separation structure. The mechanical performance of the coupled polyester manifested an obviously improved elongation at break and had a feature of higher elastic recovery rate. The results of this study indicate that the chain extension is an effective method to increase the molar mass and improve mechanical properties of waterborne polyesters.

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Synthesis of Water-Soluble Polyesters Containing Carboxy-Functional Groups in the Polymers Chain and Study of Their Metal Complexes

Cited by 8 publications

References 36 publications

Exploring copper as a catalyst for cost effective synthesis of polyfluorenes: an alternative to platinum and palladium

Exploring copper as a catalyst for cost effective synthesis of polyfluorenes: an alternative to platinum and palladium

Alkyl and allyl substituted polydibenzofluorene: blue emitters for future display applications

Preparation of waterborne elastic polyesters by chain extension with isophorone diisocyanate as a chain extender

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