Synthesis and Polymerization of Fused‐Ring Thienodipyrrole Monomers

Nguyen, Hien; Rainbolt, Elizabeth A.; Sista, Prakash; Stefan, Mihaela C.

doi:10.1002/macp.201100608

Cited by 16 publications

(12 citation statements)

References 42 publications

(37 reference statements)

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“…This is the first report on the synthesis of PTMG using anhydrous FeCl 3 without additional solvent. This catalyst is particularly promising for the scalable and economical production of PTMG because FeCl 3 is a relatively nontoxic, environmentally benign, and abundant reagent . Moreover, no halogenated by‐products, which are difficult to separate from PTMG and have a detrimental effect on the polymer properties, are formed during the polymerization process.…”

Section: Introductionmentioning

confidence: 99%

“…This catalyst is particularly promising for the scalable and economical production of PTMG because FeCl 3 is a relatively nontoxic, environmentally benign, and abundant reagent. [23][24][25][26][27][28][29] Moreover, no halogenated by-products, which are difficult to separate Additional Supporting Information may be found in the online version of this article. from PTMG and have a detrimental effect on the polymer properties, are formed during the polymerization process.…”

Section: Introductionmentioning

confidence: 99%

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Highly efficient ring‐opening polymerization of tetrahydrofuran by anhydrous ferric chloride

Yang

Yoon

Park

et al. 2019

J of Applied Polymer Sci

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Poly(tetramethylene ether glycol) (PTMG), widely used as a precursor in the fabrication of commodity polymers, is typically produced byacid‐catalyzed polymerization of tetrahydrofuran (THF). Herein, we report a detailed investigation of the cationic ring‐opening polymerization of THF catalyzed by ferric chloride (FeCl3), which can be considered as a strong Lewisacid. The polymerization reactions were performed in the presence of acetic anhydride at 20°C with FeCl3, which readily produced poly(tetramethylene ether glycol diester) (PTMG_DE). A maximum yield of 79.2% was obtained within 30 min using a FeCl3 to acetic anhydride molar ratio of 5:4. The resulting polymers generally exhibited low molecular weights and a narrow polydispersity index and could be easily converted into PTMG using aqueous NaOH. In contrast with the FeCl3‐acetic anhydride system, other iron‐based catalysts such as FeCl2 and FeCl3·6H2O did not show any noticeable activity in the polymerization of THF. The proposed mechanism involves initiation of the acetyl cation generated by FeCl3, propagation by nucleophilic addition of THF, and termination by the acetate anion, accounting for the high activity of the FeCl3 catalyst for THF polymerization. © 2019 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 47999.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Highly efficient ring‐opening polymerization of tetrahydrofuran by anhydrous ferric chloride

Yang

Yoon

Park

et al. 2019

J of Applied Polymer Sci

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“…Hybrid nanomaterials based on the conjugated polymers such as polyaniline (PANI), polythiophene, polypyrrole or poly (3-hexylthiophene) and inorganic semiconductors can be applied for degradation of organic pollutants in aqueous phase [12][13][14][15][16]. Among conjugated polymers, polyaniline (PANI) is one of the most commonly used polymers due to good stability, non-toxicity, low synthesis cost, optical, and electrical properties and high electron mobility [17].…”

Section: Introductionmentioning

confidence: 99%

Hybrid TiO<sub>2</sub>-Polyaniline Photocatalysts and Their Application in Building Gypsum Plasters

Sulowska¹,

Wysocka²,

Pelczarski³

et al. 2020

Preprint

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Hybrid materials of conjugated polymer and titanium(IV) oxide have attracted considerable attention concerning potential benefits, including (i) efficient exploitation of visible light, (ii) high adsorption capacity for organic contaminants, (iii) effective charge carriers separation. The new class of the photocatalysts is promising for the removal of environmental pollutants in both aqueous and gaseous phases. For the first time, in this study, the PANI/TiO2 hybrid composite was used for the degradation of phenol in water and toluene in the gas phase. Polyaniline-TiO2 was prepared by in-situ polymerization of aniline on the TiO2 surface. The obtained hybrid material was characterized by diffuse reflectance spectroscopy (DR/UV-Vis), X-ray diffraction (XRD), fast-Fourier transformation spectroscopy (FTIR), photoluminescence (PL) spectroscopy, microscopy analysis (SEM/TEM) and thermogravimetric analysis (TGA). An insight into the mechanism was shown based on the photodegradation analysis of charge carriers scavengers. Polyaniline is an efficient TiO2 photosensitizer for photodegradation in visible light (λ> 420 nm). The trapping experiments revealed that mainly h+ and ˙OH were reactive oxygen species responsible for phenol degradation. Furthermore, the PANI-TiO2 hybrid nanocomposite was used in gypsum plaster to study the self-cleaning properties of the obtained building material. The effect of PANI-TiO2 content on hydrophilic/hydrophobic properties and crystallographic structure of gypsum was studied. The obtained PANI-TiO2 modified gypsum plaster had improved photocatalytic activity in the reaction of toluene degradation under Vis light.

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“…8 Though not extensively investigated in OSCs as thiophene, pyrrole-containing OSCs are shown to be excellent electronic materials for organic electronic applications. 34−36 High electron density, challenging synthesis, and less air stability of the pyrrole-unit limit their use as OSCs. Fusing thiophene with pyrrole generates a relatively stable TP unit with strong donor character, and more importantly, solubilizing groups can be easily added via the pyrrolic nitrogen atom.…”

Section: Introductionmentioning

confidence: 99%

Thieno[3,2-b]pyrrole and Benzo[c][1,2,5]thiadiazole Donor–Acceptor Semiconductors for Organic Field-Effect Transistors

et al. 2019

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Two p-type donor–acceptor (D–A) semiconducting small molecules were synthesized to investigate the effect of the backbone curvature on the organic field-effect transistor performance. The backbone curvature of the donor–acceptor small molecules was modified by changing the spacer group from bithiophene to thienothiophene. Bithiophene to thienothiophene spacer groups were placed between 4H-thieno[3,2-b]pyrrole (donor) and benzo[c][1,2,5]thiadiazole (acceptor) to generate TP-BT4T-TP and TP-BT2TT-TP donor–acceptor molecules. A good charge carrier mobility of 2.59 × 10–2 cm2 V–1 s–1 was measured for the curved molecule (TP-BT4T-TP), while the linear molecule analog (TP-BT2TT-TP) only gave a low mobility of 5.41 × 10–5 cm2 V–1 s–1 after annealing at 120 °C in bottom-contact bottom-gate devices. Out-of-plane grazing-incidence X-ray diffraction analysis revealed more drastic thermally induced crystallinity for TP-BT4T-TP as compared to TP-BT2TT-TP, explaining the difference observed in the performance of devices fabricated from each molecule.

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Synthesis and Polymerization of Fused‐Ring Thienodipyrrole Monomers

Cited by 16 publications

References 42 publications

Highly efficient ring‐opening polymerization of tetrahydrofuran by anhydrous ferric chloride

Highly efficient ring‐opening polymerization of tetrahydrofuran by anhydrous ferric chloride

Hybrid TiO<sub>2</sub>-Polyaniline Photocatalysts and Their Application in Building Gypsum Plasters

Thieno[3,2-b]pyrrole and Benzo[c][1,2,5]thiadiazole Donor–Acceptor Semiconductors for Organic Field-Effect Transistors

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