A novel quinoxaline bearing electroactive monomer: Pyrrole as the donor moiety

Taskin, Asli Tuba; Balan, Abidin; Epik, Bugra; Yildiz, Ersin; Udum, Yasemin Arslan; Toppare, Levent

doi:10.1016/j.electacta.2009.04.042

Cited by 16 publications

(8 citation statements)

References 31 publications

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“…[8][9][10][11] Although many pyrrole containing conjugated polymers are used to construct electrochromic devices, few of them satisfied the green color in neutral states which is significant for RGB devices. [12,13] Recently, quinoxaline and benzotriazole inserted pyrrole derivatives were synthesized and characterized in terms of their electrochromic properties. [14] However, new donor-acceptordonor type materials with pyrrole moiety should show up in the field to enhance device properties.…”

Section: Introductionmentioning

confidence: 99%

Neutral‐State Green Conjugated Polymers from Pyrrole Bis‐Substituted Benzothiadiazole and Benzoselenadiazole for Electrochromic Devices

Baran

Öktem

Celebi

et al. 2011

Macro Chemistry & Physics

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Two donor/acceptor/donor‐type pyrrole‐incorporated monomers, 4,7‐di(1H‐pyrrol‐2‐yl)benzo[c][1,2,5]thiadiazole (M1) and 4,7‐di(1H‐pyrrol‐2‐yl)benzo[c][1,2,5]selenadiazole (M2), were synthesized and polymerized electrochemically. The resulting polymers (P1 and P2) were investigated in terms of their electrochromic and optical properties. Spectroelectrochemistry studies revealed that both polymers show two distinct absorptions in both red and blue regions. The absorptions at around 400 and 700 nm correspond to neutral‐state green polymers P1 and P2, which is a unique property for conjugated polymers. Optical band gaps were calculated as 1.12 and 1.08 eV for P1 and P2, respectively. magnified image

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Section: Introductionmentioning

confidence: 99%

Neutral‐State Green Conjugated Polymers from Pyrrole Bis‐Substituted Benzothiadiazole and Benzoselenadiazole for Electrochromic Devices

Baran

Öktem

Celebi

et al. 2011

Macro Chemistry & Physics

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“…As the optical contrast, response times, coloration efficiency, and stability of poly‐(3HTP) were compared with the quinoxaline derivatives in literature, it is clear that poly‐(3HTP) is a promising polymer as an electrochromic material. The high optical contrast (∆ T %) especially in the NIR region exceeds those of reported such as P(PTQ), PDBQTh PDBQEd, PDEFNQ, PHTQ, PHTBQ, PHTPP, and PPHED . Thus, poly‐(3HTP) can be used in various NIR region applications.…”

Section: Resultsmentioning

confidence: 99%

A Novel Near‐IR Effective Pyrene‐Based Donor–Acceptor Electrochrome

Sefer

Hacıoğlu

Tonga

et al. 2015

Macro Chemistry & Physics

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In this work, a novel donor-acceptor electrochromic monomer (3HTP), containing a pyrene subunit connected to a quinoxaline acceptor bridge, is synthesized. The corresponding polymer, poly-(3HTP), is directly deposited onto an indium tin oxide (ITO)/glass surface via an electrochemical process. Atomic force microscopy (AFM) images reveal that the electrochemically deposited poly-(3HTP) has a smooth surface due to self-assembly of the planar pyrene subunit. Electrochemical and optical properties are investigated via cyclic voltammetry and UV-vis absorption measurements. The polymer fi lm shows a multielectrochromic feature at both anodic and cathodic regimes. Poly-(3HTP) exhibits a strong near-infrared (NIR) absorption at the oxidized state with an optical contrast of 88% (at 1800 nm), a very fast response time of 0.5 s and fast switching times, and longterm stability. Density functional theory calculations reveal that the molecule has a high planarity, and the NIR absorption arises from a strong intramolecular charge transfer from the polymer backbone to the planar pyrene subunit. Synthesis of 10,13-Bis(4-hexylthiophen-2-yl)phenanthro[4,5-abc]phenazine (3HTP)10,13-Dibromophenanthro[4,5-abc]phenazine (0.46 g, 1 mmol) and tributylstannyl-3-hexylthiophene (0.96 g, 2.1 mmol) were dissolved in 20 mL toluene, and the solution was purged with Macromol. Chem. Phys. 2015, 216, 829−836 Scheme 1. Synthetic route to 3HTP monomer. Macromol. Chem. Phys. 2015, 216, 829−836NIR region exceeds those of reported such as P(PTQ), [ 40 ] PDBQTh [ 41 ] PDBQEd, [ 41 ] PDEFNQ, [ 42 ] PHTQ, [ 43 ] PHTBQ, [ 24 ] PHTPP, [ 24 ] and PPHED. [ 44 ] Thus, poly-(3HTP) can be used in various NIR region applications.

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“…Toppare research group made use of highly substituted quinoxaline derivatives as monomers in the synthesis of conducting polymers 18, 21–26. These molecules appeared to be good candidates for PET reactions with aryliodonium salts due to their extended conjugation, low oxidation potentials, and high solubility in various monomers.…”

Section: Resultsmentioning

confidence: 99%

“…conducting polymers. 18,[21][22][23][24][25][26] These molecules appeared to be good candidates for PET reactions with aryliodonium salts due to their extended conjugation, low oxidation potentials, and high solubility in various monomers. 2,3-bis(3,4-bis(decyloxy)phenyl)-5,8-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl) quinoxaline (DOPEQ, I), one of the aforementioned quinoxaline derivatives, was chosen to be tested as an electrontransfer dye photosensitizer.…”

Section: Dopeq As An Electron-transfer Dye Photosensitizermentioning

confidence: 99%

A quinoxaline derivative as a long wavelength photosensitizer for diaryliodonium salts

Bulut

Günbaş

Toppare

2009

J. Polym. Sci. A Polym. Chem.

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This article reports the use of a quinoxaline derivative as a photosensitizer for diaryliodonium salt photoinitiators. 2,3‐bis(3,4‐bis(decyloxy)phenyl)‐5,8‐bis(2,3‐dihydrothieno[3,4‐b][1,4]dioxin‐5‐yl)quinoxaline (DOPEQ), is a highly conjugated compound with strong absorption bands at wavelengths ranging from 300 to 550 nm and is shown to facilitate photoinitiated cationic polymerization of heterocyclic monomers such as oxiranes and oxetanes. The polymerizations are initiated at room temperature by using long wavelength UV light in the presence of diphenyliodonium hexafluorophosphate (Ph2I+PF 6−). The polymerizations are monitored by optical pyrometry (OP). It is also possible to initiate photopolymerizations with ambient solar irradiation in the presence of this photosensitizer dye. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 209–213, 2010

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A novel quinoxaline bearing electroactive monomer: Pyrrole as the donor moiety

Cited by 16 publications

References 31 publications

Neutral‐State Green Conjugated Polymers from Pyrrole Bis‐Substituted Benzothiadiazole and Benzoselenadiazole for Electrochromic Devices

Neutral‐State Green Conjugated Polymers from Pyrrole Bis‐Substituted Benzothiadiazole and Benzoselenadiazole for Electrochromic Devices

A Novel Near‐IR Effective Pyrene‐Based Donor–Acceptor Electrochrome

A quinoxaline derivative as a long wavelength photosensitizer for diaryliodonium salts

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