Clickable, versatile poly(2,5-dithienylpyrrole) derivatives

Çamurlu, Pınar; Karagoren, Nese

doi:10.1016/j.reactfunctpolym.2013.03.014

Cited by 31 publications

(32 citation statements)

References 33 publications

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“…Amplification of the polarization potential beyond 1.0 V resulted in a steady increase in the current density indicating formation of radical cation of pyrrole unit. [29,30] Such behavior is in accordance with literature [31][32][33] and Py4N 3 as seen in Figure 1(c). Starting from the second scan (Figure 1(d)), a new quasi…”

Section: Synthesis Of Pyrrole Derivativessupporting

confidence: 92%

Ferrocene clicked polypyrrole derivatives: effect of spacer group on electrochemical properties and post-polymerization functionalization

Çamurlu

Guven

Bi̇ci̇l

2016

Designed Monomers and Polymers

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In this study, novel ferrocene-functionalized N-alkyl substituted pyrrole derivatives, namely 4-ferrocenyl-1-[3-(pyrrol-1-yl)propyl]-1H-1,2,3-triazole (Py3Fc), 4-ferrocenyl-1-[4-(pyrrol-1-yl)butyl]-1H-1,2,3-triazole (Py4Fc), and 4-ferrocenyl-1-[6-(pyrrol-1-yl)hexyl]-1H-1,2,3-triazole (Py6Fc), were synthesized via click reaction and the monomers were characterized by 1 H NMR, 13 C NMR, FTIR, and HRMS techniques. Redox properties of the monomers were investigated by cyclic voltammetry (CV) studies. Contrary to general literature, both Py4Fc and Py6Fc were electrochemically polymerized without loss in redox activity of ferrocene group. Moreover, click chemistry was utilized in postpolymerization functionalization. For this purpose, three azide-containing polypyrroles, P(Py3N 3 ), P(Py4N 3 ), and P(Py6N 3 ) were electrochemically synthesized and subjected to click reaction in the presence of ethynylferrocene. CV studies of the post-polymerization functionalized polymers revealed quasi-reversible waves, while only P(Py6-post-Fc) showed the characteristic redox behavior of both polypyrrole and ferrocene. Thus, in this study preparation of a conducting homopolymers of pyrrole having covalently bonded ferrocene units was demonstrated and effect of spacer group is investigated.

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Section: Synthesis Of Pyrrole Derivativessupporting

confidence: 92%

Ferrocene clicked polypyrrole derivatives: effect of spacer group on electrochemical properties and post-polymerization functionalization

Çamurlu

Guven

Bi̇ci̇l

2016

Designed Monomers and Polymers

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“…Propargyl‐pyrene was easily synthesized in a one‐pot reaction with ca 50% yield by the reaction of 1‐pyrenylmethanol with propargyl bromide in the presence of NaH. SNS‐N 3 was used as the azide functionalized partner and a typical click reaction in the presence of CuSO 4 and sodium ascorbate in acetone/water as the solvent system was performed (Scheme ). The monomer (SNS‐pyrene) was fully characterized by 1 H NMR (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…1‐Pyrenemethanol, 1,4‐dioxane, NaH, propargyl bromide, methanol, dichloromethane (CH 2 Cl 2 ), NaSO 4 , hexane, ethyl acetate, tetrahydrofuran (THF), CuSO 4 .5H 2 O, sodium ascorbate, thiophene, succinyl chloride, ethanolamine, p‐toluene sulfonic acid, triethylamine, dimethylaminopyridine, p‐toluene sulfonyl chloride, sodium azide, EDOT and acetonitrile (ACN) were used as received. 1,4‐di(2‐thienyl)‐1,4‐butanedione, 2‐(2,5‐di‐thiophene‐2‐yl‐pyrrol‐1‐yl)‐ethanol, toluene‐4‐sulfonic acid 2‐(2,5‐di‐thiophen‐2‐yl‐pyrrol‐1‐yl)‐ethyl ester and 1‐(2‐azido‐ethyl)‐2,5‐dithiophen‐2‐yl‐1H‐pyrrole (SNS‐N 3 ) were synthesized according to the literature …”

Section: Methodsmentioning

confidence: 99%

Multichromic polymers based on pyrene clicked thienylpyrrole

2014

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“…The first one is first electrochemical polymerization of 1-(2-azidoethyl)-2,5-di-thiophen-2-yl-1H-pyrrole (3) to yield PSNS-N 3 (P15) films on ITO electrodes. Afterward, the PSNS-N 3 coated ITO electrode was reacted with 2 in the presence of CuSO 4 and sodium ascorbate, and the PSNS-Fc (P16) coated electrode was obtained with potential usages as electrocatalysts, biosensors, and gas sensors [45]. Another strategy is first to perform the CuAAC of 3 and 2, then electrochemically polymerized the precursor monomer of SNS-Fc (4), and PSNS-Fc films on ITO electrodes were finally prepared [46].…”

Section: Click Modification Of General Polymersmentioning

confidence: 99%

Click Chemistry: A Powerful and Versatile Methodology for Preparation of Ferrocene-Containing Polymers

Yao

Sun

Qin

et al. 2014

J Inorg Organomet Polym

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Ferrocene-containing polymers (FcPs) have attracted much research interest in the last decade, due to their unique properties and enormous applications. However, it is a great synthetic challenge to prepare FcPs before the advent of click chemistry. In this review, we summarized the recent research efforts on synthesizing FcPs through click reactions, which include click modification of preformed polymers and click polymerization of ferrocene (Fc) containing monomers. Due to the containing Fc moieties, the FcPs enjoy excellent redox activity, thermal stability, electrochemical property, and magnetism. Accordingly, they are promising to be used as electro-

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Clickable, versatile poly(2,5-dithienylpyrrole) derivatives

Cited by 31 publications

References 33 publications

Ferrocene clicked polypyrrole derivatives: effect of spacer group on electrochemical properties and post-polymerization functionalization

Ferrocene clicked polypyrrole derivatives: effect of spacer group on electrochemical properties and post-polymerization functionalization

Multichromic polymers based on pyrene clicked thienylpyrrole

Click Chemistry: A Powerful and Versatile Methodology for Preparation of Ferrocene-Containing Polymers

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