Novel poly(2,5-dithienylpyrrole) (PSNS) derivatives functionalized with azobenzene, coumarin and fluorescein chromophore units: spectroelectrochemical properties and electrochromic device applications

Yiğit, Deniz; Hacıoğlu, Şerife O.; Güllü, Mustafa; Toppare, Levent

doi:10.1039/c4nj02098g

Cited by 19 publications

(12 citation statements)

References 52 publications

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“…These characteristics have allowed the development of many technological applications [3], from organic and molecular electronic [4,5] to sensors [6][7][8] or smart surfaces [9][10][11][12][13]. Among many types of CPs, poly(thienyl-pyrrole-thienyl) derivatives have received great interest [14][15][16][17][18] especially for their electrochromic properties [19][20][21][22][23]. The structure of derivatives is generated from a central pyrrole units bearing two thiophene moieties attached on the C2 and C5 carbon atoms of the pyrrole and can be named SNS or Poly(SNS).…”

Section: Introductionmentioning

confidence: 99%

Dithienylpyrrole Electrografting on a Surface through the Electroreduction of Diazonium Salts

et al. 2020

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The control of the interface and the adhesion process are key issues for the development of new application based on electrochromic materials. In this work the functionalization of an electrode’s surface through electroreduction of diazonium generated in situ from 4-(2,5-di-thiophen-2-yl-pyrrol-1-yl)-phenylamine (SNS-An) has been proposed. The synthesis of the aniline derivative SNS-An was performed and the electrografting was investigated by cyclic voltammetry on various electrodes. Then the organic thin film was fully characterized by several techniques and XPS analysis confirms the presence of an organic film based on the chemical composition of the starting monomer and allows an estimation of its thickness confirmed by AFM scratching measurements. Depending on the number of electrodeposition cycles, the thickness varies from 2 nm to 10 nm, which corresponds to a few grafted oligomers. In addition, the grafted film showed a good electrochemical stability depending on the scan rates up to 400 V/s and the electrochemical response of the modified electrode towards several redox probes showed that the attached layer acts as a conductive switch. Therefore, the electrode behaves as a barrier to electron transfer when the standard redox potential of the probe is below the layer switching potential, whereas the layer can be considered as transparent towards the electron transfer for redox probes with a redox potential above it.

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Section: Introductionmentioning

confidence: 99%

Dithienylpyrrole Electrografting on a Surface through the Electroreduction of Diazonium Salts

et al. 2020

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“…For the first cycle scan, the irreversible oxidation peaks are observed at 0.8 V (DTC), 0.9 V (BCB), 0.98 V (BCP), which can be assigned to oxidation of the monomers to produce free radical. 32 With the number of cycles increasing, the new peaks at lower potential than monomer appear and the height of these peaks are found to be successively growing for the next cycle, implying that more conjugated electroactive species can form on the ITO / glass electrode surface. Moreover, all the CVs show two redox peaks, indicating that polaronic and bipolaronic formation of the occurred polymer chain can be observed during the electrochemical process, which is benefit for multi-color electrochromism.…”

Section: Resultsmentioning

confidence: 99%

Electrochemical and Spectroelectrochemical Properties of Poly(carbazole-EDOT)s Derivatives Functionalized with Benzonitrile and Phthalonitrile Units

Luo

Jin

et al. 2015

ECS J. Solid State Sci. Technol.

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Two novel carbazole-3, 4-ethoxylenedioxythiophene (EDOT) derivatives containing acceptor groups such as benzonitrile and phthalonitrile were synthesized and characterized. Both the monomers could be electrochemically polymerized and form stable electroactive polymer films. Spectroelectrochemical technique were performed to investigate the electrochemical and optical changes of the resulting polymer films, multi-electrochromic properties upon different applied potentials suggested the effect of the benzonitrile and phthalonitrile units and their potential applications in electrochromic device. Furthermore, scanning electron micrographs (SEM) were used to study the microstructure morphology of polymer films. Conjugated polymers have potential applications in the fields of field effect transistors (FETs), 1,2 electrochromic devices (ECDs), 3,4 organic light emitting diodes (OLEDs) 5,6 and supercapacitors 7,8 due to their low cost synthesis, ease in tuning the electronic and optical properties and good electrochemical stability. Particularly, electrochromic polymer materials have attracted great interest thanks to their various colors with the same materials, high optical contrast ratios, fast switching ability and outstanding coloration efficiency (CE). [9][10][11][12] Recently, design and synthesis of new electrochromic polymers with better electrochromic properties and exploring the relationship between polymer structure and their performance are still the focus of this area. 13,14 Among conjugated polymers, much attention is paid to carbazole and its derivatives due to their easily modified by introduction of new groups to many sites such as (2,7-), (3,6-), and N-positions. 15-18Comparing with poly(2,7-carbazole)s, poly(3,6-carbazole)s show potential multi-color properties because of the conjugation breaks. 19,20 poly(3,6-carbazole)s based on the donor groups (thiophene, furan, selenophene) of the conjugated main chain have been investigated and show good electrochromic properties. [21][22][23][24][25] However, for almost all the reported studies, alkyl groups are introduced into the Nposition of poly(3,6-carbazole)s, few papers are about importing the acceptor units into the N-position and exploring the effects on the performance. [26][27][28] In our previous works, 29,30 D-A structure based on the 3, 6-carbazole and thiophene were studied, and the results showed that the electrochromic properties can be tuned by changing the acceptor group at N-position of carbazole. What's more, electrochromic performance can be enhanced by introducing the EDOT into the conjugated chain of polymer, implying that polymers based on 3, 6-carbazole and EDOT with D-A structure may have some specific features.In this context, two novel monomers based on 3, 6-carbazole and EDOT functionalized with benzonitrile and phthalonitrile units were synthesized and characterized. Both polymers could be electrochemically prepared on the surface of ITO / glass electrode, and their electrochemical and electrochromic properties were investigated ...

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“…-Konjuge organik iletken polimerler sahip oldukları iyi elektriksel iletkenlik, yüksek yük transfer kabiliyeti, kolay işlenebilirlik ve düşük maliyet gibi özelliklerinden dolayı günümüz plastik elektronik teknolojisinde sıklıkla tercih edilen önemli bir elektroaktif malzeme sınıfıdır. Organik iletken polimer türevleri son yirmi yıllık süreçte, elektrokromik cihazlar [1,2], organik fotovoltaik hücreler [3,4], organik ışık saçan diyotlar [5,6], transistörler [7,8] ve sensörler [9,10] başta olmak üzere farklı birçok teknolojide kendisine uygulama alanı bulmuştur. Son zamanlarda, -konjuge organik iletken polimerlerin kullanıldığı bir diğer alan ise süperkapasitörlerdir.…”

Section: Introductionunclassified

2,3-Di(tiyofen-3-il)piperazin Monomerlerinin Ultrases Destekli Sentezi, İletken Polimerlerinin Hazırlanması ve Süperkapasitör Davranışlarının İncelenmesi

Yiğit

2022

Düzce Üniversitesi Bilim Ve Teknoloji Dergisi

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Bu çalışmada, 2,3-di(tiyofen-3-il)piperazin esaslı iletken polimer türevlerinin elektrokimyasal yük depolama özellikleri incelenmiştir. Bu amaçla, ilk önce, ultrases destekli bir yöntem kullanılarak 2,3-di(tiyofen-3il)piperazin halka sistemine sahip yeni elektroaktif monomerlerin sentezi gerçekleştirilmiştir. 2,3-Di(tiyofen-3il)piperazin monomerleri elektrokimyasal olarak paslanmaz çelik substrat yüzeylerinde polimerleştirilmiş ve poli(2,3-di(tiyofen-3-il)piperazin (PTTP) ve poli(2,3-di(tiyofen-3-il)dekahidrokinoksalin (PTTQ) esaslı redoks aktif elektrot malzemeleri hazırlanmıştır. PTTP ve PTTQ redoks aktif malzemelerinin kapasitif performansları dönüşümlü voltametri (CV), galvanostatik şarj-deşarj (GCD) ve elektrokimyasal impedans spektroskopi (EIS) teknikleri kullanılarak araştırılmıştır. PTTP ve PTTQ esaslı elektrot malzemeleri 2,5 mAcm -2 sabit akım yoğunluğunda 175 Fg -1 ve 198 Fg -1 spesifik kapasitans değerlerine ulaşmıştır. Ayrıca, PTTP ve PTTQ, sırasıyla, 70,2 Whkg -1 ve 87,1 Whkg -1 enerji yoğunluğu değerleri ile 7 kWkg -1 ve 6,2 kWkg -1 güç yoğunluğu değerleri sergilemiştir. Bunun yanı sıra, PTTP ve PTTQ elektrot malzemeleri 10 000 şarj-deşarj döngüsü sonunda %80 ve %87,5 gibi oldukça yüksek uzun döngü ömrü kararlılıkları göstermiştir. Kapasitif performans test sonuçları PTTP ve PTTQ redoks aktif elektrot malzemelerinin yüksek performanslı pratik süperkapasitör uygulamalarında kullanılabilecek potansiyele sahip ümit vaat eden elektrot malzemeleri olduğunu ortaya koymuştur.

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Novel poly(2,5-dithienylpyrrole) (PSNS) derivatives functionalized with azobenzene, coumarin and fluorescein chromophore units: spectroelectrochemical properties and electrochromic device applications

Abstract: The combination of strong chromophore units and a 2,5-dithienylpyrrole (SNS) monomer backbone resulted in interesting electrochemical and spectroelectrochemical behaviors.

Cited by 19 publications

References 52 publications

Dithienylpyrrole Electrografting on a Surface through the Electroreduction of Diazonium Salts

Dithienylpyrrole Electrografting on a Surface through the Electroreduction of Diazonium Salts

Electrochemical and Spectroelectrochemical Properties of Poly(carbazole-EDOT)s Derivatives Functionalized with Benzonitrile and Phthalonitrile Units

2,3-Di(tiyofen-3-il)piperazin Monomerlerinin Ultrases Destekli Sentezi, İletken Polimerlerinin Hazırlanması ve Süperkapasitör Davranışlarının İncelenmesi

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