13669-05-1Relevant articles and documents
Synthesis and application of poly-SNS-anchored carboxylic acid: A novel functional matrix for biomolecule conjugation
Ekiz, Fulya,Ouzkaya, Funda,Akin, Mehriban,Timur, Suna,Tanyeli, Cihangir,Toppare, Levent
, p. 12337 - 12343 (2011)
Here we report the synthesis of a novel conducting polymer and its properties as an immobilization platform for biosensor application. The conducting polymer has functional groups used for the formation of amide bonding with the enzyme immobilized on the polymer surface. After covalent immobilization of glucose oxidase (GOx) on the polymeric matrix, its application for glucose biosensing was investigated in detail. Scanning electron microscopy (SEM), X-ray photoelectron spectroscopy (XPS) and contact angle measurements were used to monitor the surface properties of the polymer before and after biomolecule conjugation. The optimized biosensor showed a very good linearity between 0.01 mM and 1.2 mM, a 13 s response time and a detection limit (LOD) of 0.004 mM to glucose. Also, kinetic parameters, operational and storage stabilities were determined. Apparent Michaelis constant (Km app) and Imax values of 1.17 mM and 11.28 μA, respectively, were obtained.
Synthesis and spectroscopic characterization on 4-(2,5-di-2-thienyl-1H-pyrrol-1-yl) benzoic acid: A DFT approach
Kurt,Sas, E. Babur,Can,Okur,Icli,Demic,Karabacak,Jayavarthanan,Sundaraganesan
, p. 8 - 17 (2016)
Abstract A complete structural and vibrational analysis of the 4-(2,5-di-2-thienyl-1H-pyrrol-1-yl) benzoic acid (TPBA), was carried out by ab initio calculations, at the density functional theory (DFT) method. Molecular geometry, vibrational wavenumbers a
Effect of sodium naphthalenide, a key SET reagent, on trifluoroacetyl derivatives
Banerji, Avijit,Bandyopadhyay, Debasish,Basak, Bidyut,Sur, Kumar R.,Paul, Jyoti N.,Banerji, Julie,Chatterjee, Asima
, p. 7033 - 7035 (2005)
Aromatic trifluoroacetyl derivatives on treatment with single electron transfer (SET) reagent, sodium naphthalenide, yield symmetrical defluorinated dimers, whereas for aliphatic trifluoroacetyl compounds the reaction usually fails. Investigations have been made for different substituents as well as for similar types of chloro and bromo compounds to establish the scope of the reaction.
New pyrimidines incorporating thiophene and pyrrole moieties: synthesis and electrochemical polymerization
Bushueva, Anastasiya Yu.,Shklyaeva, Elena V.,Abashev, Georgii G.
, p. 329 - 331 (2009)
The synthesis and electrochemical polymerization on the indium-tin oxide covered glass plates of two new substituted pyrimidines, namely, (1H-pyrrol-1-yl)-4,6-di(thiophen-2-yl)pyrimidine and [2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl]-4,6-di(thiophen-2-yl)-pyrimidine was performed; the structure of the latter was determined by X-ray methods.
Multielectrochromic amide-based poly(2,5-dithienylpyrrole) bearing a fluorene derivative: Synthesis, characterization, and optoelectronic properties
Neto, Jorge L.,da Silva, Luis P.A.,da Silva, Joel B.,Ferreira, Raul L.,da Silva, Ana Júlia C.,da Silva, Júlio C.S.,de Oliveira, ítalo N.,Lima, Dimas J.P.,Ribeiro, Adriana S.
, (2021)
A novel 2,5-dithienylpyrrole derivative bearing a fluorene substituent (SNSFCA) was synthesized and successfully electropolymerized on ITO electrodes in acetonitrile (CH3CN) containing tetrabutylammonium tetrafluoroborate ((C4H9)4NBF4). The fluorescence properties of SNSFCA and its polymer (PSNSFCA) were investigated upon laser excitation at 337 nm, however, the polymer was not fluorescent, which may be explained by DFT methods. PSNSFCA films present multielectrochromism in a narrow range of applied potential (0.0 ≤ E ≤ 0.4 V vs. Ag/Ag+), as shown by the track of the CIE 1931 xy chromaticity coordinates, besides high absorption in the near infrared (NIR) region. The electrochromic properties of PSNSFCA films, such as good chromatic contrast (Δ%T), coloration efficiency (η) in the range of 110–350 cm2 C?1, and stability to redox cycling aroused the possibility of its application as an electrochromic material in optoelectronic devices.
Design of a biosensor based on 1-(4-nitrophenyl)-2,5-di(2-thienyl)-1H pyrrole
Tuncagil, Sevinc,Varis, Serhat,Toppare, Levent
, p. 195 - 199 (2010)
Immobilization of polyphenol oxidase (tyrosinase, E.C. 1.14.18.1) was achieved on a copolymer of 1-(4-nitrophenyl)-2,5-di(2-thienyl)-1H-pyrrole [SNS(NO2)] with pyrrole ([SNS(NO2)]/PPy) via electrochemical polymerization. Two different substrates; catechol and l-tyrosine were used for the characterization of biosensor. The kinetic parameters of the biosensor, maximum reaction rate of the enzyme (Vmax) and Michaelis-Menten constant (Km) were determined for two different substrates. Vmax was found as 0.02 μmol/min electrode for both substrates. Km values were determined as 250 and 2 mM for catechol and l-tyrosine respectively. Calibration curves for enzyme activity versus substrate concentration were plotted between 0.05 and 0.5 M catechol and between 0.8 and 2.5 mM l-tyrosine. Optimum temperature and pH, operational and storage stabilities of immobilized enzyme were examined.
Electrochemical synthesis, characterization and capacitive properties of novel thiophene based conjugated polymer
?elik, Burcu,?elik, Ilhami,Dola?, Hacer,G?r?ay, Hakan,?ahin, Yücel,Sara?, A. Sezai,Pekmez, Kadir
, p. 107 - 112 (2014)
In this paper, a novel thiophene based monomer, 1-(pyren-1-yl)-2,5- di(thiophen-2-yl)-1H-pyrrole, PThP, was synthesized and characterized by 1H NMR and 13C NMR spectroscopic methods. The electrochemical behavior and electropolymerization of this novel monomer were performed on pencil graphite electrode (PGE) by cyclic voltammetry. The effect of solvent, dopant, scan number and scan rate on the electropolymerization and properties of the conjugated polymer films were investigated. The capacitive properties of the poly(PThP) films were tested by electrochemical impedance spectroscopy (EIS). The highest specific capacitance value was calculated for the conjugated polymer modified PGE that was obtained in 0.1 M tetrabutylammonium perchlorate/dichloromethane solution for 30 cycles at 25 mV/s scan rate as 25.45 mF cm-2. The surface morphologies of the conjugated polymer modified electrodes were determined by scanning electron microscopy (SEM).
Electrochromic properties of multicolored novel polymer synthesized via combination of benzotriazole and N-functionalized 2,5-di(2-thienyl)-1H-pyrrole units
Rende, Eda,Kilic, Cihan E.,Udum, Yasemin Arslan,Toffoli, Daniele,Toppare, Levent
, p. 454 - 463 (2014)
Synthesis of new conducting polymers is desired since their electrochemical and optical properties enable them to be used as active layers in many device applications. Benzotriazole and N-functionalized 2,5-di(2-thienyl)-1H-pyrrole (SNS Series) containing polymers showed very promising results as electrochromic materials. In order to observe the effect of the combination of these two units, three new monomers; 2-(6-(2,5-bis(5-methylthiophen-2-yl)-1H-pyrrol-1-yl) hexyl)-4,7-di(thiophen-2-yl)-2H benzo[d][1,2,3]triazole (M1), 2-(6-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl)hexyl)-4,7-di(thiophen-2-yl) -2H-benzo[d][1,2,3]triazole (M2) and 2-(6-(2,5-di(thiophen-2-yl)-1H-pyrrol-1-yl) hexyl)-4,7-bis(5-methylthiophen-2-yl)-2H-benzo[d][1,2,3]triazole (M3) were synthesized. To better characterize the electronic and spectroscopic properties of the monomers, density functional theory (DFT) and its time-dependent generalization (TD-DFT) were used to calculate their vertical ionization potentials, vertical electron affinity and to simulate and interpret their infrared and UV-vis spectra. The monomers were electrochemically polymerized and the resultant polymers were characterized with cyclic voltammetry and UV-vis-NIR spectroscopy techniques. An electrochromic device was constructed with electrochemical polymer of M2. The device switched between red and blue colors and showed exceptional optical memory.
The new branched multielectrochromic materials: Enhancing the electrochromic performance via longer side alkyl chain
Baycan Koyuncu, Fatma,Sefer, Emre,Koyuncu, Sermet,Ozdemir, Eyup
, p. 8407 - 8414 (2011)
We describe the synthesis and structure-property relationships of two branched electroactive monomers containing carbazole core, 2,5-di(2-thienyl)-1H- pyrrole, differentiated by the length of side alkyl chains (DSNSC-1 and DSNSC-2). Structural identification of initial compounds and products were carried out by using FT-IR and 1H and 13C NMR spectroscopy. The electroactive materials DSNSC-1 and DSNSC-2 were directly coated on to ITO glass surface by using electrochemical polymerization process. The results clearly indicate that the length of side alkyl chain has a major impact on optical and electrochemical properties of these polymers. Poly-DSNC-2 with longer side alkyl chain exhibits a high contrast ratio (ΔT% = 68% at 850 nm), a response time of about 0.8 s, and high coloration efficiency (352 cm2 C-1) and retained its performance by 97.1% even after 5000 cycles.
Fast switching, high contrast multichromic polymers from alkyl-derivatized dithienylpyrrole and 3,4-ethylenedioxythiophene
Camurlu, Pinar,Gültekin, Cemil,Bicil, Zeynep
, p. 50 - 56 (2012)
In this report we disclose the synthesis and characterization of optoelectronic properties of a novel conducting polymer based on 1-(2-ethyl-hexyl)-2,5-di-thiophen-2-yl-2,3-dihydro-1H-pyrrole, (SNS-HE). Additionally, copolymers based on SNS-HE and 3,4-ethylenedioxythiophene (EDOT) were electrochemically synthesized and characterized. Cyclic voltammetry, FTIR, spectroelectrochemistry analyses confirmed that the resulting polymers were true copolymers having distinct electrochromic properties from that of the parent homopolymers. Depending on the synthesis conditions, the SNS-HE based polymers exhibited optical band gaps ranging from 2.32 to 1.70 eV and the copolymers displayed multichromism within a wide range of the visible spectrum. The copolymers revealed shorter switching times (around 0.5 s) and higher optical contrast (around 36%). Our studies have shown that color of the copolymers could be easily tuned by controlled increase in copolymerization potential. Moreover, a prototype of the all solid state poly(SNS-HE-EDOT)/PEDOT complementary electrochromic device was fabricated in order to investigate the utilization of these polymers. These devices exhibited short switching times with reasonable open circuit memory under atmospheric conditions.
Synthesis and electrochemical polymerization of 4,7-Di(2-thienyl)indene
Abashev,Begishev,Bushueva,Romanova,Shklyaeva
, p. 1440 - 1443 (2010)
4,7-Di(2-thienyl)indene was prepared, and its electrochemical behavior was studied. Pleiades Publishing, Ltd., 2010.
A new ITO-compatible side chain-functionalized multielectrochromic polymer for use in adaptive camouflage-like electrochromic devices
Koyuncu, Sermet,Koyuncu, Fatma Baycan
, p. 174 - 180 (2018)
In this study, a new electroactive monomer, 3-(2-[4-(2,5-di-2-thienyl-1H-pyrrol-1-yl)phenyl]ethyl-thio)propanoic acid (SNSPA), was synthesized and then deposited onto the ITO/glass surface by an electrochemical process. When positive potentials were applied on the polymer film of SNSPA, the film at the neutral state turned from orange to green (0.6 V) and then to blue (1.1 V) because of the presence of polaronic and bipolaronic species on the SNS main chain of the polymer. At the last stage, a complementary electrochromic device was constructed by using poly(SNSPA) as the anode layer and PEDOT:PSS as the cathode layer. A fast response time (about 0.5 s) and a high stability of about 98% were obtained at the end of 1000 cycles. The capability of the proposed polymer to undergo reversible color change among brown, green, and blue is a significant property for use as an adaptive camouflage material for all conditions of sand, forest, and sea for military applications.
A new low band gap electrochromic polymer containing 2,5-bis-dithienyl-1H- pyrrole and 2,1,3-benzoselenadiazole moiety with high contrast ratio
Baycan Koyuncu, Fatma,Sefer, Emre,Koyuncu, Sermet,Ozdemir, Eyup
, p. 5772 - 5779 (2011)
A new low band gap electrochromic polymer containing of 3-(2,5-di-2-thienyl-1H-pyrrol-1-yl)-9-ethyl-9H-carbazole (SNSC) and 2,1,3-benzoselenadiazole (BSe) moiety has been reported. Structural identification of initial compounds and product were carried out by using FT-IR and 1H NMR spectroscopy results. The resulting polymer, poly(SNSC-BSe), was completely soluble in various common organic solvents and its weight-average molecular weight (Mw) were 9420 (PDI: 1.22). According to AFM results, the RMS (root mean surface) roughness of poly-(SNSC-BSe) was found to be 48.6 nm. Besides, the thermogravimetric analysis presented that the poly(SNSC-BSe) is moderately stable against to thermal effect with the initial degradation temperature at 182 °C. The lowest energy transition band maxima of poly(SNSC-BSe) was 498 nm in thin film and the optical band gap calculated from the onset wavelength of the optical absorption was 1.77 eV. On the other hand, the electrochemical band gap calculated from oxidation and reduction onset values was 1.60 eV, respectively. Finally, the electrochromic performance of the polymer film represents a high contrast ratio in the NIR region (51%), fast response time of about 1 s, high coloration efficiency (274 cm2 C-1) and retained its performance by 94.6% even after 1000 cycles.
Copper(I)/DDQ-Mediated Double-Dehydrogenative Diels-Alder Reaction of Aryl Butenes with 1,4-Diketones and Indolones
Chen, Jie,Hu, Wei,Wang, Min,Xu, Wen-Lei,Zhao, Wei-Ming,Zhou, Ling
supporting information, p. 7169 - 7174 (2020/10/12)
A copper(I)/DDQ-mediated double-dehydrogenative Diels-Alder (DDDA) reaction of simple butenes with 1,4-diketones and indolones has been established for the first time. This strategy is based on a tandem double-dehydrogenation/Diels-Alder reaction from nonprefunctionalized starting materials, in which both a diene and dienophile were in situ generated via activation of fourfold inert C(sp3)-H bonds in one catalytic system.
Oligothienyl catenated germanes and silanes: Synthesis, structure, and properties
Zaitsev, Kirill V.,Lam, Kevin,Poleshchuk, Oleg Kh.,Kuz'Mina, Lyudmila G.,Churakov, Andrei V.
supporting information, p. 5431 - 5444 (2018/04/23)
The synthesis of two new groups of oligothienyl catenated silanes and germanes, Me5M2Thn (1a-b), Me5M2ThnM2Me5 (2a-c) (terminal), and ThnM2Me4Thn (3a-d) (internal) (M = Si, Ge; n = 2, 3; Th = 2- or 2,5-thienyl), is reported. The study of their structural parameters as well as of their spectral (NMR), electrochemical (CV) and optical (UV/vis absorbance, luminescence) properties has been performed in detail; in addition, the unexpected compound [Th2Si2Me4Th]2 (3a′) is also studied. Theoretical investigations have been performed for model compounds in order to establish structure-property relationships. The molecular structures of 2a (Me5Si2Th2Si2Me5), 2b (Me5Ge2Th2Ge2Me5), 3a (Th2Si2Me4Th2) and 3b (Th2Ge2Me4Th2) have been investigated by X-ray diffraction analysis. An effective conjugation with flattening of both Th planes in terminal 2a and 2b was observed. The main trends in the dependence of the optical and electrochemical properties on the structural parameters have been established. All of the compounds studied exhibit a strong emission within the 378-563 nm range, and the maximal quantum yield (up to 77%) is observed for the Si derivative 3a′. For the majority of the compounds, the quantum yields (20-30%) are significantly larger than for 2,2′-bi- and 2,2′:5′,5′′-terthiophenes. Due to their good emission properties, these compounds could be used to develop new materials with specific spectral properties.
