Phenothiazine derivatives, diketopyrrolopyrrole-based conjugated polymers: synthesis, optical and organic field effect transistor properties

Truong, Nhung Thanh Thi; Nguyễn, Linh Hồ Thùy; Thi, Huyen Le; Doan, Bao Kim; Tran, Dat Hung; Truong, Khuong Tung; Nguyen, Viet Quoc; Nguyen, Le‐Thu T.; Hoang, Mai Ha; Pham, Toai Van; Nguyen, Vuong Mau; Huynh, Tien; Doan, Tin Chanh Duc; Nguyên, Hà Trần

doi:10.1007/s10965-020-02199-x

Cited by 9 publications

(5 citation statements)

References 44 publications

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“…[12][13][14][15] However, the donor-acceptor (D-A) concept can be considered as one of the most critical modifications in order to tune the band gap of the CPs. 16 In literature, thienopyrroledione (TPD), diketopyrrolopyrrole (DPP), benzooxadiazole (BO), benzotriazole (BTz), and benzothiadizole (BT) [17][18][19][20][21] are classified as the most used electronwithdrawing aromatic heterocycles. Lately, benzothiadiazole gains significant attention due to its comprising strong electron-accepting sulfur atom and two imine (−C=N−) bonds in its skeleton.…”

mentioning

confidence: 99%

Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via π Bridges

Karaman

Goker

Hacıoğlu

et al. 2021

J. Electrochem. Soc.

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Four novel benzo[c][1,2,5]thiadiazole comprising monomers namely 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-di(thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TBTT), 5-fluoro-4,7-bis(4-hexylthiophen-2-yl)-6-((2-octyldodecyl)oxy)benzo[c][1,2,5]thiadiazole (HTBTHT), 5-fluoro-4,7-di(furan-2-yl)-6-((2-octyldodecyl)oxy)benzo- [c][1,2,5]thiadiazole (FBTF), and 5-fluoro-6-((2-octyldodecyl)oxy)-4,7-bis(thieno[3,2-b]thiophen-2-yl)benzo[c][1,2,5]thiadiazole (TTBTTT) were designed, and synthesized successfully via Stille polycondensation reaction. The structural characterizations of the monomers were performed by 1H and 13C NMR spectroscopy and High Resolution Mass Spectroscopy (HRMS). The monomers were then electropolymerized in a three electrode cell system via cyclic voltammetry. The electrochemical, and spectroelectrochemical characterization of the polymers were reported in detail. Besides, theoretical calculations were performed to elucidate observed experimental properties. According to the cyclic voltammogram of the polymers, HOMO and LUMO energy levels were calculated as −5.68 eV/−3.91 eV, −5.71 eV/−3.72 eV, −5.61 eV/−4.04 eV, and −5.51 eV/−3.71 eV and the electronic band gaps were 1.77 eV, 1.99 eV, 1.57 eV, and 1.80 eV for PTBTT, PHTBTHT, PFBTF, and PTTBTTT, respectively.

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confidence: 99%

Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via π Bridges

Karaman

Goker

Hacıoğlu

et al. 2021

J. Electrochem. Soc.

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“…Indeed, phenothiazine is a polyaromatic structure absorbing in the visible range, even without substituents, so that various Type I and Type II photoinitiators were designed and synthesized with this structure [191][192][193][194][195][196][197]. This is also an excellent electron donor that was extensively used for the design of push-pull dyes developed for different applications in organic electronics such as energy conversion [198][199][200][201][202][203][204][205][206][207][208][209][210], light-emitting materials for organic light-emitting diodes (OLEDs) [211][212][213][214][215][216][217][218][219][220][221][222][223] or semi-conductors for organic field effect transistors (OFETs) [199,[224][225][226][227][228][229]. Phenothiazines were also developed as fluorescent probes for the detection of various molecules and ions in organic and aqueous solutions, food, live cells and animals [230][231][232]…”

Section: Phenothiazine Derivativesmentioning

confidence: 99%

Recent Advances in Monocomponent Visible Light Photoinitiating Systems Based on Sulfonium Salts

Dumur

2023

Polymers

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During the last decades, multicomponent photoinitiating systems have been the focus of intense research efforts, especially for the design of visible light photoinitiating systems. Although highly reactive three-component and even four-component photoinitiating systems have been designed, the complexity to elaborate such mixtures has incited researchers to design monocomponent Type II photoinitiators. Using this approach, the photosensitizer and the radical/cation generator can be combined within a unique molecule, greatly simplifying the elaboration of the photocurable resins. In this field, sulfonium salts are remarkable photoinitiators but these structures lack absorption in the visible range. Over the years, various structural modifications have been carried out in order to redshift their absorptions in the visible region. In this work, an overview of the different sulfonium salts activable under visible light and reported to date is proposed.

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“…[113][114][115][116][117][118] Numerous drugs have also been prepared with the phenothiazine scaffold as exemplified with thioridazine, chlorpromazine, fluphenazine, perphenazine, prochlorperazine and others biologically active products. [119] Similarly to carbazole, phenothiazine is also an excellent electron-donating group and this group was extensively used for the design of chromophore for solar cells, [120][121][122][123][124][125][126][127], light-emitting materials for electroluminescent devices, [128][129][130][131][132] semiconductors for organic field effect transistors (OFETs) [133][134][135][136][137][138] or fluorescent probes. [139][140][141][142] Based on these strong knowledges concerning phenothiazine chemistry, a wide range of phenothiazine-based oxime esters were designed and synthesized starting from 2017.…”

Section: Introductionmentioning

confidence: 99%

Recent advances on phenothiazine-based oxime esters as visible light photoinitiators of polymerization

Dumur

2024

European Polymer Journal

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Phenothiazine derivatives, diketopyrrolopyrrole-based conjugated polymers: synthesis, optical and organic field effect transistor properties

Cited by 9 publications

References 44 publications

Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via π Bridges

Altering Electronic and Optical Properties of Novel Benzothiadiazole Comprising Homopolymers via π Bridges

Recent Advances in Monocomponent Visible Light Photoinitiating Systems Based on Sulfonium Salts

Recent advances on phenothiazine-based oxime esters as visible light photoinitiators of polymerization

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