Thiophene substituted phenothiazine polymers: Design, synthesis and characterization

Tezel, Ruhiye Nilay; Kaya, İsmet

doi:10.1016/j.arabjc.2018.09.004

Cited by 5 publications

(9 citation statements)

References 21 publications

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“…The appearance of a broad band in the region of 650 nm suggests the occurrence of PHT oligomerization. The oligomerization leads to the polyconjugation of molecular bonds that are responsible for the spectral redshift 16 . During incubation with Fe 2 O 3 NRW, the radical cation signals decreased while the signals assigned to PHT oligomerization increased.…”

Section: Resultsmentioning

confidence: 99%

“…The oligomerization leads to the polyconjugation of molecular bonds that are responsible for the spectral redshift. 16 During incubation with Fe 2 O 3 NRW, the radical cation signals decreased while the signals assigned to PHT oligomerization increased. The isosbestic point at 556 nm indicates that the oligomers are formed directly by the reaction between PHT •+ molecules.…”

Section: Generation Of Pht •+mentioning

confidence: 96%

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Oligomerization of photochemically oxidized phenothiazine by nanostructured α‐Fe₂O₃

Sobrinho

Nascimento

Icimoto

et al. 2023

Polymer International

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Phenothiazines (PTZs) and their derivatives are a group of compounds that have diverse applications in medicine, the dye industry and advanced materials. Due to the electron–hole donating characteristic, these compounds have also been applied in batteries and solar energy devices. PTZs can be converted into stable radical cations by chemical and photochemical reactions. The PTZ radical cations are reactive for polymerization. The photochemical formation of PTZ radical cations is favored in aggregates by the Type I mechanism in which one molecule in the triplet excited state abstracts one electron from a neighbor molecule. In the present study, 10H‐phenothiazine (PHT) was dissolved in chloroform and converted to the radical cation species (PHT•+) by UV light irradiation. The radical cation was characterized by UV–visible absorption and electron paramagnetic resonance techniques. Addition of α‐Fe2O3 nanorods and nanowires to PHT•+ chloroform solution promoted its color change from orange to blue‐green. Absorption measurement revealed a significant decrease of the UV and visible bands assigned to radical cation species and the appearance of a broad band at the spectral region of 650 nm. The blue‐green solution was dried, leading to the formation of crystals that were characterized using the X‐ray diffraction technique. Considering possible PHT oligo(poly)merization, the crystals were analyzed using matrix‐assisted laser desorption ionization time‐of‐flight mass spectrometry that corroborated the formation of oligomers containing three, four and five PHT residues and their sulfoxide derivatives. The PHT oligomers retained photosensitivity and exhibited an electron paramagnetic resonance signal indicating possible applications as hole donors in electronic devices. Oligomerization was also obtained by aggregation of PHT•+ in sodium dodecylsulfate micelles indicating that proximity and orientation of the free radical molecules is the mechanism for the oligomerization. Therefore, a new route for PHT oligomerization catalyzed by α‐Fe2O3 nanowires is proposed. The method is readily available, inexpensive and environmentally safe. © 2022 Society of Industrial Chemistry.

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Section: Resultsmentioning

confidence: 99%

Section: Generation Of Pht •+mentioning

confidence: 96%

Oligomerization of photochemically oxidized phenothiazine by nanostructured α‐Fe₂O₃

Sobrinho

Nascimento

Icimoto

et al. 2023

Polymer International

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“…For the TBB unit, the peak of the phenyl ring (b, 4H, s) appeared at 7.11 ppm, and the thiophene-bound methylene protons (c, 4H, t) appeared at 4.63 ppm [ 54 ]. For PTHH, the methylene protons of the aliphatic subunit bounded to the thiophene moieties showed peaks between 4.22 and 4.41 ppm, while the methylene not bound to the thiophene moieties (e, f, 8H, m) appeared in the range of 1.21–2.01 ppm [ 55 ]. In PTB x H y , the assigned peaks (b, c and d) corresponded to the aromatic segment induced by TBB units, whereas the peaks (d, e and f) described the aliphatic characteristic of THH units shifting to lower values, typical of aliphatics (1,6-HDO).…”

Section: Resultsmentioning

confidence: 99%

Synthesis by Melt-Polymerization of a Novel Series of Bio-Based and Biodegradable Thiophene-Containing Copolyesters with Promising Gas Barrier and High Thermomechanical Properties

et al. 2023

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Volatile global oil prices, owing to the scarcity of fossil resources, have impacted the cost of producing petrochemicals. Therefore, there is a need to seek novel, renewable chemicals from biomass feedstocks that have comparable properties to petrochemicals. In this study, synthesis, thermal and mechanical properties, and degradability studies of a novel series of sustainable thiophene-based copolyesters like poly(hexylene 2,5-thiophenedicarboxylate-co-bis(2-hydroxyethoxybenzene) (PTBxHy) were conducted via a controlled melt polymerization method. Fourier-transform infrared (FTIR) and nuclear magnetic resonance (1H NMR) spectroscopy techniques elucidated the degree of randomness and structural properties of copolyesters. Meanwhile, gel permeation chromatography (GPC) analysis showed a high average molecular weight in the range of 67.4–78.7 × 103 g/mol. The glass transition temperature (Tg) was between 69.4 and 105.5 °C, and the melting point between 173.7 and 194.2 °C. The synthesized polymers outperformed poly(ethylene 2,5-thiophenedicarboxylate) (PETF) and behaved similarly to poly(ethylene terephthalate) (PET). The copolyesters exhibited a high tensile strength of 46.4–70.5 MPa and a toughness of more than 600%, superior to their corresponding homopolyesters. The copolyesters, which ranged from 1,4-bis(2-hydroxyethyl)benzene thiophenedicarboxylate (TBB)-enriched to hexylene thiophenedicarboxylate (THH)-enriched, offered significant control over crystallinity, thermal and mechanical properties. Enzymatic hydrolysis of synthetized polymers using porcine pancreatic lipase (PP-L) over a short period resulted in significant weight losses of 9.6, 11.4, 30.2, and 35 wt%, as observed by scanning electron microscopy (SEM), with perforations visible on all surfaces of the films. Thus, thiophene-based polyesters with cyclic aromatic structures similar to terephthalic acid (TPA) show great promise as PET mimics. At the same time, PP-L appears to be a promising biocatalyst for the degradation of bioplastic waste and its recycling via re-synthesis processes.

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“…Structural Characterization 3,7-di-2-thienyl-10H-phenothiazine used in electropolymerization was synthesized from 3,7-dibromo-10Hphenothiazine according to standard literature procedures [11]. The chemical structure of each compound was confirmed by FT-IR, 1H-NMR, and 13C-NMR spectra.…”

Section: Resultsmentioning

confidence: 99%

“…Here, it is aimed to synthesize phenothiazine copolymers by constant potential electrolysis. For this, the monomer was prepared as described in the literature [11]. The structure of the synthesized monomers was illuminated by FT-IR, UV-Vis, 1H-and 13 C-NMR techniques.…”

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confidence: 99%

A Kinetic Evaluation for Phenothiazine Based Copolymers

Doğan¹

2021

Hittite J. Sci. Eng.

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T he first conductive polymers were discovered in 1975. Then, they have attracted considerable attention due to their interesting electrical conductivity [1]. Nowadays, the studies related to conductive polymers have gained a new acceleration due to the rapid developments in science and technology. In most of these studies, it is aimed to give to the polymeric materials some properties of semiconductors. Some properties which do not naturally exist in semiconductors are trying to be imparted to conductive polymers synthetically [2]. Since conductive polymer compounds, which are the product of polymerization, have a wide area in polymer technology, comprehensive studies have been carried out to date [3,4]. Among these conductive polymers, phenothiazine based polymers has been extensively studied for their applications in various electronic and electrochemical legal devices [5,6]. They are good electron-donor and hole transport materials, since the phenotiazine rings have electron-rich sulfur and nitrogen heteroatoms. However, many of their features are still known to be limited. On the other hand, to date, various methods have been used for the synthesis of conductive polymers. Chemical, enzymatic, oxidative, and electrochemical polymerization methods are used effectively for the conversion of monomers carrying groups such as thiophene, pyrrole, and carbazole to conductive

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Thiophene substituted phenothiazine polymers: Design, synthesis and characterization

Cited by 5 publications

References 21 publications

Oligomerization of photochemically oxidized phenothiazine by nanostructured α‐Fe₂O₃

Oligomerization of photochemically oxidized phenothiazine by nanostructured α‐Fe₂O₃

Synthesis by Melt-Polymerization of a Novel Series of Bio-Based and Biodegradable Thiophene-Containing Copolyesters with Promising Gas Barrier and High Thermomechanical Properties

A Kinetic Evaluation for Phenothiazine Based Copolymers

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Thiophene substituted phenothiazine polymers: Design, synthesis and characterization

Cited by 5 publications

References 21 publications

Oligomerization of photochemically oxidized phenothiazine by nanostructured α‐Fe2O3

Oligomerization of photochemically oxidized phenothiazine by nanostructured α‐Fe2O3

Synthesis by Melt-Polymerization of a Novel Series of Bio-Based and Biodegradable Thiophene-Containing Copolyesters with Promising Gas Barrier and High Thermomechanical Properties

A Kinetic Evaluation for Phenothiazine Based Copolymers

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Oligomerization of photochemically oxidized phenothiazine by nanostructured α‐Fe₂O₃

Oligomerization of photochemically oxidized phenothiazine by nanostructured α‐Fe₂O₃