500772-26-9Relevant academic research and scientific papers
Fluorene-dithienothiophene- S,S -dioxide copolymers. Fine-tuning for OLED applications
Osken, Ipek,Gundogan, Ali Senol,Tekin, Emine,Eroglu, Mehmet S,Ozturk, Turan
, p. 9202 - 9210 (2014/01/06)
Three groups of fluorene-dithieno[3,2-b;2′,3′-d]thiophene-S,S- dioxides (DTT-S,S-dioxide) copolymers, each having four different ratios of DTT-S,S-dioxide (5, 15, 25, and 50%) were successfully synthesized through Suzuki coupling method. While the first group copolymers P1 had direct connection of fluorene to the peripheral thiophenes of DTT-S,S-dioxide, second group copolymers P2 had a thiophene extension between fluorene and DTT-S,S-dioxide, and in the third group, copolymers P3, fluorene had a connection with DTT-S,S-dioxide through the phenyl moiety of DTT. Absorbance and emission measurements of first two groups P1 and P2 displayed a regular bathochromic shift with increasing content of DTT-S,S-dioxide, which was more clearly observed in their solid state fluorescence measurements. Introduction of thiophene to the peripherals of the DTT-S,S-dioxide in copolymers P2 caused even further bathochromic shift in absorbances and emissions. As the absorbance and emission of P1 went up to 447 and 558 nm in solution, respectively, P2 had them at 472 and 592 nm, respectively. In solid state, emissions of P1 and P2 even went further up to 585 and 646 nm, respectively. The bathochromic trend of P1 and P2 became opposite with absorbance and solid state emission of P3, which had a hypsochromic shift with increasing content of DTT-S,S-dioxide. Solid state emission of P3, particularly the copolymers having 5, 15 and 50% DTT-S,S-dioxide, covered a wide region between 400 and 675 nm. A spread of colors from light blue (border of white) to red through green and yellow was obtained with the OLED applications of the copolymers. Their optical and electronic band gaps varied between 2.17 and 2.99 eV and between 2.68 and 3.57 eV, respectively. While the highest quantum yield was obtained with P2 (5%) as 0.66, the lowest was observed with P2 (50%) as 0.03. Almost all of the polymers displayed good thermal stabilities. No weight loss was observed with the copolymers P2 (5-15%) and P3 up to 400 C.
Rigid-core fluorescent oligothiophene-S,S-dioxide isothiocyanates. Synthesis, optical characterization, and conjugation to monoclonal antibodies
Sotgiu, Giovanna,Zambianchi, Massimo,Barbarella, Giovanna,Aruffo, Fabio,Cipriani, Franco,Ventola, Alfredo
, p. 1512 - 1520 (2007/10/03)
In this paper we report the synthesis of a new class of fluorescent thiophene-based isothiocyanates containing a 3,5-disubstituted dithieno [3,2-b:2′,3′-d] thiophene-4,4-dioxide moiety as the rigid core, using the palladium-catalyzed cross-coupling reaction of aryl stannanes with aryl bromides (Stille coupling). By changing the molecular structure through the progressive addition of thienylene or phenylene units, light emission from blue to orange was obtained. Photoluminescence quantum yields ranged from 0.65 to 0.90 for blue and green light emitters to 0.10-0.35 for yellow and orange ones. Optically and chemically stable fluorescent bioconjugates were prepared by spontaneous reaction of the isothiocyanates with monoclonal antibodies anti-CD3 and anti-CD8 in slightly basic solutions.
