Multichromic polymers based on pyrene clicked thienylpyrrole

Guven, Nese; Çamurlu, Pınar; Yucel, Baris

doi:10.1002/pi.4847

Cited by 14 publications

(5 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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%

“…Moreover, many synthesis pathways have been developed to couple the SNS moieties and other monomers. Recently, Guven et al reported the synthesis of several SNS derivatives by click chemistry opening the way for new materials in electrochromic applications [20][21][22]. This approach allows one to achieve an effective post-polymerization functionalization of azide containing SNS monomer.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Dithienylpyrrole Electrografting on a Surface through the Electroreduction of Diazonium Salts

et al. 2020

View full text Add to dashboard Cite

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.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Dithienylpyrrole Electrografting on a Surface through the Electroreduction of Diazonium Salts

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Examples include SNS derivatives with substituted naphthalene group, 7 additional pyrrole group, 8 phenyl groups, [9][10][11] indan and 1,3-benzodioxole groups, 12 pyridinyl and phenanthroline groups, 13 benzoic acid group, 14 nitrophenyl group, 15 short alkyl groups 16 etc. Since the Paal-Knorr reaction can have relatively low yields, an innovative approach based on click chemistry has been proposed by our group leading to synthesis of SNS derivatives with substituted naphthalimide, 17 anthracene, 18 pyrene, 19 fluorene and carbazole units. 20 In addition, an ingenious approach, focused on click functionalization of the SNS polymer rather than the SNS monomer has been developed.…”

Section: The Novelty/significance Of Thiophene-pyrrole Hybrid Structuresmentioning

confidence: 99%

Review—Functional Platforms for (Bio)sensing: Thiophene-Pyrrole Hybrid Polymers

Apetrei

Çamurlu

2020

J. Electrochem. Soc.

Self Cite

View full text Add to dashboard Cite

The synthesis of thiophene-pyrrole hybrid polymers has become of increased interest due to their potential in a wide range of applications, from optoelectronics to biodevices. While the extended application of these materials in optoelectronics or photovoltaics has been previously addressed, a comprehensive account on their potential for application in sensorics has not been reported so far. The main advantages derived from their application are related to facility in synthesis and stable electrochemical behavior with the added benefit of tailor-made functionality. As it has become clear that the ultimate goal in electrochemical sensing is the preparation of a conducting platform that not only exhibits satisfactory conductivity but also contains functional groups that are able to connect to the desired bio-element, the hybrid polymers appear very promising. Preparation of conducting platforms with tailored functionality such as poly(2,5-di(thienyl)pyrrole)s and poly(dithieno(3,2-b:2′,3′-d)pyrroles)s represents an excellent opportunity for achieving stable immobilization and maintaining adequate orientation of biomolecules, whilst improving the electron transfer, resulting in highly sensitive and stable biosensors. The current review briefly addresses the synthesis of hybrid thiophene-pyrrole molecules detailing several approaches and, subsequently, focuses on their application as polymeric bioimmobilization platforms for electrochemical detection of relevant bio-analytes, bio-receptors or DNA hybridization events.

show abstract

“…Recently, a number of SNS derivatives have been reported and displayed specific electrochromic properties. Camurlu et al synthesized anthracene- and pyrene-containing thienylpyrrole derivatives (SNS-Anth [24] and SNS-pyrene [25]) and reported their multichromic properties. Koyuncu et al reported the synthesis and electrochromic characterizations of a novel polymer (PSNS-PDI) consisting of SNS-donor and PDI-acceptor units [26].…”

Section: Introductionmentioning

confidence: 99%

Applications of Tris(4-(thiophen-2-yl)phenyl)amine- and Dithienylpyrrole-based Conjugated Copolymers in High-Contrast Electrochromic Devices

Chung

2016

Polymers

View full text Add to dashboard Cite

Abstract:Tris(4-(thiophen-2-yl)phenyl)amine-and dithienylpyrrole-based copolymers (P(TTPA-co-DIT) and P(TTPA-co-BDTA)) were electropolymerized on ITO electrode by applying constant potentials of 1.0, 1.1, and 1.2 V. Spectroelectrochemical investigations revealed that P(TTPA-co-DIT) film displayed more color changes than P(TTPA-co-BDTA) film. The P(TTPA-co-DIT) film is yellow in the neutral state, yellowish-green and green in the intermediate state, and blue (1.2 V) in highly oxidized state. The ∆T max of the P(TTPA-co-DIT) and P(TTPA-co-BDTA) films were measured as 60.3% at 1042 nm and 47.1% at 1096 nm, respectively, and the maximum coloration efficiency (η) of P(TTPA-co-DIT) and P(TTPA-co-BDTA) films were calculated to be 181.9 cm 2¨C´1 at 1042 nm and 217.8 cm 2¨C´1 at 1096 nm, respectively, in an ionic liquid solution. Dual type electrochromic devices (ECDs) consisting of P(TTPA-co-DIT) (or P(TTPA-co-BDTA)) anodic copolymer, ionic liquid-based electrolyte, and poly(3,4-(2,2-diethylpropylenedioxy)thiophene) (PProDOT-Et 2 ) cathodic polymer were constructed. P(TTPA-co-BDTA)/PProDOT-Et 2 ECD showed high ∆T max (48.1%) and high coloration efficiency (649.4 cm 2¨C´1 ) at 588 nm. Moreover, P(TTPA-co-DIT)/PProDOT-Et 2 and P(TTPA-co-BDTA)/PProDOT-Et 2 ECDs displayed satisfactory optical memory and long term switching stability.

show abstract

Multichromic polymers based on pyrene clicked thienylpyrrole

Abstract: Pyreneclicked SNS was subjected to electrochemical homo‐ and copolymerization. Copolymers exhibit multichromic behavior with low band gaps and switching times. Fine tuning of the colors was achieved through control of the copolymerization potential.

Cited by 14 publications

References 46 publications

Dithienylpyrrole Electrografting on a Surface through the Electroreduction of Diazonium Salts

Dithienylpyrrole Electrografting on a Surface through the Electroreduction of Diazonium Salts

Review—Functional Platforms for (Bio)sensing: Thiophene-Pyrrole Hybrid Polymers

Applications of Tris(4-(thiophen-2-yl)phenyl)amine- and Dithienylpyrrole-based Conjugated Copolymers in High-Contrast Electrochromic Devices

Contact Info

Product

Resources

About