Synthesis and characterization of novel poly(<i>p</i>‐phenylenevinylene) derivatives containing phenothiazine‐5‐oxide and phenothiazine‐5, 5‐dioxide moieties

Yang, Liying; Wang, C.; Li, Liqiang; Janietz, Silvia; Wedel, Armin; Yang, Hua; Yin, Shougen

doi:10.1002/pola.22171

Cited by 18 publications

(12 citation statements)

References 17 publications

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“…Phenothiazine contains electron-rich atoms N and S atoms, possesses a low oxidation potential, and is capable to form stable cation-radicals. The unique electronic and optical characteristics of phenothiazine proceed from its nonplanar geometry providing thereby the possibility to obtain π-packed aggregates and intermolecular excimers [5]. It has been established in our previous research that chalcones prepared on the base of carbazole, phenothiazine, and their substituted derivatives appeared to be good for creation of electrochromic polymer films [6][7][8].…”

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confidence: 99%

New thiophene- and phenothiazine-containing chalcones: Synthesis, and electrochemical properties

et al. 2014

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Among the conjugated systems used in design of electronic devices based on organic materials the derivatives of carbazole and phenothiazine occupy are of key importance due to their high thermal stability, hole conductivity and light emission in various spectral regions when used in OLEDs and electrochromic devices, and to hole conductivity [1][2][3][4]. Phenothiazine contains electron-rich atoms N and S atoms, possesses a low oxidation potential, and is capable to form stable cation-radicals. The unique electronic and optical characteristics of phenothiazine proceed from its nonplanar geometry providing thereby the possibility to obtain π-packed aggregates and intermolecular excimers [5]. It has been established in our previous research that chalcones prepared on the base of carbazole, phenothiazine, and their substituted derivatives appeared to be good for creation of electrochromic polymer films [6][7][8]. It is also known that chalcones containing various aromatic fragments in their structure possess nonlinear optical properties indispensable for creation of optoelectronic devices, like electro-optic modulators, optical switches, lightemitting sources, etc. [9, 10]. Therefore it is expedient to synthesize new chalcone series including in their structure various carbo-and heterocyclic fragments and to examine their physicochemical properties, first, from the viewpoint of using them for preparation of polymer compounds, and second from the standpoint of tuning their electronic and optical characteristics by modifying the chemical structure.In this study there is presented the synthesis and the investigation of physicochemical properties of chalcones IX-XII (see the scheme) containing conjugation chains formed by combinations of various carbo-and heterocyclic fragments. For preparation of these chalcones we have initially synthesized two already known methyl ketones I [11] and II [12], after that a thiophene fragment was introduced into their structure. At the first stage of the synthesis the Vilsmeier-Haak-Arnold reaction was carried out to prepare compounds III and IV, their cyclization with chloroacetone in the presence of Na 2 S afforded methyl ketones V and VI used further as methylene components in the synthesis of chalcones [11,13,14].Refluxing of the obtained methyl ketones V and VI with 4-(10N-phenothiazin-10-yl)-and 4-(9N-carbazol-9-yl)benzaldehydes VII and VIII in the alkaline alcohol solution gave rise to the target chalcones IX-XII. Thus prepared chalcones are the dark red or orange crystalline substances, well soluble in common organic solvents, and their solutions in dichloromethane possess a pronounced yellow and yellow-green fluorescence, and in hexane -a blue one. UV absorption and fluorescence spectra of compounds V, VI and IX-XII were recorded for their solutions in chloroform. Stokes shifts were estimated from the data of absorption and emission spectra. On the basis of the value of the longest absorption wavelength (λ onset ) the width of the forbidden band gap (E g opt ) was calculated [15...

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confidence: 99%

New thiophene- and phenothiazine-containing chalcones: Synthesis, and electrochemical properties

et al. 2014

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“…Recently, phenothiazine polymers have been used in PLEDs,7–11 organic field‐ effect transistors (OFETs),12, 13 and organic solar cells,7, 12, 14–17 due to their good electro‐optical properties. Due to its electron‐rich nature, phenothiazine is an excellent building block for lowering the ionic potential of conjugated polymers and for promoting better injection and transportation of holes across the polymeric backbone 10, 18. Phenothiazine polymers also display higher quantum efficiencies as its nonplanarity prevents π‐stacking aggregation and intermolecular excimer formation 19, 20.…”

Section: Introductionmentioning

confidence: 99%

“…In spite of these properties, all the reported phenothiazine polymers have relatively poor light‐emitting performance. A few research groups have reported phenothiazine copolymers for PLED application 7–10. For example, Jenekhe and co‐workers20 have shown that an alternating copolymer of phenothiazine and fluorene displayed an improved PLED performance as compared with the phenothiazine homopolymer due to a more balanced electron and hole transport 20…”

Section: Introductionmentioning

confidence: 99%

Phenothiazine Semiconducting Polymer for Light‐Emitting Diodes

Elkassih

Sista

Magurudeniya

et al. 2012

Macro Chemistry & Physics

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Phenothiazine alternating copolymer poly{4,8‐bis(5‐dodecylthiophene‐2‐yl)benzo[1,2‐b:4,5‐b′]dithiophene‐alt‐(10‐decylphenothiazine)} (P1) is synthesized by Stille coupling polymerization. The synthesized polymer has an electrochemical bandgap of 1.61 eV and displays good photoluminescence with a quantum yield of 63.3%. The polymer is tested as a light‐emitting material in polymeric light‐emitting diodes (PLEDs) with a device structure of indium tin oxide (ITO)/poly(3,4‐ethylenedioxythiophene) poly(styrenesulfonate) (PEDOT:PSS)/polymer/Cs2CO3/Al. The devices display an orange‐yellow electroluminescence (Commission Internationale de l'Eclairage (CIE) 1931 color‐space chromaticity diagram: x = 0.5355 and y = 0.4611) with a maximum brightness of 3130 cd m−2 at an applied voltage of 10 V.

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“…As the phenothiazine unit has two electron‐rich sulfur and nitrogen heteroatoms, phenothiazine‐based polymers are good electron‐donors and hole transport materials, which have been investigated in LEDs9, 13–19 and PVDs 9, 19, 20. Recently, a phenothiazine‐based polymer, poly(3,7‐divinylene‐ N ‐octyl‐ phenothiazine‐alt‐2‐octyl‐benzotriazole) (PQTN), was synthesized in our laboratory according to the donor–acceptor‐alternating strategy 13.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of low‐band‐gap conjugated polymers containing phenothiazine and benzo‐2,1,3‐thia‐/seleno‐diazole

Xu¹,

Liu²,

Li³

et al. 2009

Polymers for Advanced Techs

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Two phenothiazine‐based conjugated polymers, poly(3, 7‐divinylene‐N‐octyl‐phenothiazine‐alt‐benzo‐2,1,3‐ thiadiazole) (PQS) and poly(3,7‐divinylene‐N‐octyl‐phenothiazine‐alt‐benzo‐2,1,3‐selenodiazole) (PQSe) were synthesized by Heck coupling reaction. The chemical structures of the two polymers were confirmed by 1H‐NMR and Ft‐IR. They showed good solubility in some common organic solvents such as tetrahydrofuran (THF), chloroform. The weight‐average molecular weight (Mw) of the polymers determined by GPC in THF against polystyrene standards was 3.7 × 103 for PQS and 1.9 × 103 for PQSe, respectively. The temperatures of 5% weight loss (T5) were 385.0°C for PQS and 324.0°C for PQSe, respectively, determined by TGA measurements under nitrogen ambience. UV–vis absorption spectra of the polymer films showed the absorption maxima at 537 nm for PQS and 539 nm for PQSe, with the full width at half maximum (FWHM) of 190 and 230 nm, respectively. The optical band gaps ($\mathop E\nolimits_g^{{\rm opt}}$) of the polymer films are 1.86 eV for PQS and 1.80 eV for PQSe, respectively. As the polymers have low‐band‐gap and broad absorption in the visible region, they may be used as potential light‐harvesting materials for photovoltaic devices (PVDs). Furthermore, photoluminescence (PL) spectra of the polymer solutions showed the emission maxima at 698 nm for PQS and 709 nm for PQSe, with FWHM of 152 nm and 167 nm, respectively, which revealed that these two polymers may be used as red and near infrared light‐emitting materials for polymeric light‐emitting diodes (PLEDs). Copyright © 2009 John Wiley & Sons, Ltd.

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Synthesis and characterization of novel poly(p‐phenylenevinylene) derivatives containing phenothiazine‐5‐oxide and phenothiazine‐5, 5‐dioxide moieties

Cited by 18 publications

References 17 publications

New thiophene- and phenothiazine-containing chalcones: Synthesis, and electrochemical properties

New thiophene- and phenothiazine-containing chalcones: Synthesis, and electrochemical properties

Phenothiazine Semiconducting Polymer for Light‐Emitting Diodes

Synthesis and characterization of low‐band‐gap conjugated polymers containing phenothiazine and benzo‐2,1,3‐thia‐/seleno‐diazole

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