Ring‐Sulfonated Poly(thienothiophene)

Abstract

with different pore sizes: a polystyrene±block±poly(ethylene oxide) (SE1010) provided by Goldschmidt for the material M5 (made as described previously [7]), a hydrogenated polybutadiene±block±poly (ethyleneoxide) (PBPEO20) for the material M13 (made as described previously [9]), and an aqueous polystyrene latex dispersion (LAT) with a solid content of 9 % for the material M60 (made in analogy to a previous method [10]).The dried and aged silica gels were calcined in a muffle-type furnace at 550 C for 6 h. The resultant mesoporous matrices where characterized by TEM and nitrogen sorption measurements (BET). Table 2 summarizes the composition of the synthesized materials.Synthesis of the g-C 3 N 4 Nanospheres: Cyanamide (CH 2 N 2 ) was used as a molecular precursor because its low melting point (47 C) allows convenient filling of the silica matrices by soaking at slightly elevated temperatures. The monolithic silica material was placed in liquid cyanamide at 70 C and kept there for 30 min. The monoliths were then taken out, dried in air, and the surface-adsorbed cyanamide molecules were washed away by dipping in ethanol.When the hybrid material was dry again, the reaction was carried out by heating the monolith under flowing N 2 up to 550 C with a heating ramp of 5 K min ±1 . Three hours of isothermal treatment completed the reaction.The monoliths were then crushed into a fine powder with a ball mill and treated with an excess of hydrofluoric acid (5 %) twice for 24 h to free the C 3 N 4 spheres from the silica matrix. The centrifuged C 3 N 4 powder was separated from the HF solution and washed with distilled water. Note that special precautionary measures are required when working with HF.The purity of the samples and the silica leftovers were determined by thermogravimetric analysis (TGA). The samples were temperature-stable up to 550 C and contained 2±5 % silica residue.Characterization of the Materials: TEM images were taken with a Zeiss EM 912X at an acceleration voltage of 120 kV. SEM was performed on a Zeiss DSM 940 A. Tapping-mode AFM images were recorded with a multimode atomic force microscope from Veeco Instruments using Olympus microcantilevers (resonance frequency: 300 kHz; force constant: 42 N m ±1 ). The samples were redispersed in water using ultrasonication and one droplet was spin-coated onto a freshly prepared mica substrate. X-ray data were recorded with a Siemens D8 diffractometer equipped with a Sol X, SI solid-state detector, using Cu Ka radiation in a symmetric reflection setup. Sorption measurements (BET) were obtained with a Micromeritics Tristar 3000. Elemental analyses (C, H, N, S) were performed on a Vario EL Elementar (Elementar Analyzen-systeme, Hanau, Germany). The IR spectra were collected with a BIORAD FTS 6000 FTIR spectrometer, equipped with an attenuated total reflection (ATR) setup. Steady-state fluorescence spectra were recorded on a Perkin±Elmer LS50B luminescence spectrometer. TGA was performed on a Netzsch TG 209. DSC was performed on a Netzsch DSC 204.

Synthesis and Preliminary In‐Vitro Cytotoxic Evaluation of Some Novel bis‐Heterocycles Incorporating Thienothiophene

“…The detected inhibitory activity against MCF-7 cells was measured for compound 23 (3.8 ± 0.4 μM) that was more potent than standard drug followed by 18,14,7,20,12,24,8,6,13, and 19 with IC 50 values of 5.1 ± 0.6; 10.6 ± 0.8; 17.0 ± 0.7; 18.4 ± 0.8; 18.7 ± 0.5; 20.4 ± 0.7; 22.9 ± 0.9; 24.4 ± 0.9; 31.2 ± 1.5, and 36.1 ± 0.7 μM, respectively. Similarly, the tested compounds showed good inhibitory effect against HepG2 cells and the order of activity is 23,18,14,24,12,7,8,20,13,6, and 19 with IC 50 values of 4.4 ± 0.6, 5.9 ± 0.7, 8.73 ± 0.6, 11.6 ± 0.8, 16.9 ± 1.3, 17.2 ± 1.2, 19.5 ± 1.4, 19.7 ± 1.1, 21.1 ± 1.5, 32.4 ± 2.3, and 37.1 ± 0.8 μM, respectively ( Table 1).…”

“…Thienothiophene and its derivatives have attracted constant interest over the past decades because of their wide range of pharmacological activities, such as antitumor, antiviral , and as antibiotic, antiglaucoma drugs, or as inhibitors of platelet aggregation . In addition, substituted thienothiophenes have been used as building blocks in the synthesis of polycondensed systems, which include sulfur analogues of electronic devices, due to their many fundamental advantages over their inorganic counterparts in achieving low‐cost, large area and mechanically flexible electronics .…”

New conjugated polymers for plastic solar cells

“…78 The monomer seems to have a low oxidation potential for polymerization and was thus studied for applications in LEDs and electrochromic devices. 79 The Ferraris' group also reported the synthesis of poly(2-phenylthieno-[3,4-b]thiophene). 80 The monomer was synthesized in only two steps.…”

Layer‐by‐Layer Self‐Assembled Multilayer Stimuli‐Responsive Polymeric Films

“…The combination of PEDOT's electrochromic and conducting capabilities with polyviologen's deep absorption at higher potentials led to a transmittance change of 82.1% with a switching speed of 0.6 s. In order to improve the device performance by removing inactive PSS, Reynolds and coworkers used a functionalized PEDOT and PAH and produced a device with 45% change in transmittance [170]. Other electrochromic materials that can undergo redox reaction including sulfonated poly(thienothiophene) [171], PB [172,173], and polyoxometalates (POMs) [174][175][176][177] have also been used to make electrochromic devices. The potential applications of these electrochromic devices include tunable windows, display panels, and smart paper.…”