231620-29-4Relevant academic research and scientific papers
Water-soluble fluorescent polymers that respond to singlet oxygen
Altinok, Esra,Frausto, Fanny,Thomas, Samuel W.
, p. 2526 - 2535 (2016/07/14)
Although acenes with more than three fused rings can both fluoresce efficiently and react with singlet oxygen (1O2) rapidly, their hydrophobic nature presents a challenge to their use in aqueous environments. Herein we report a series of fluorescent, water-soluble random copolymers that each comprise (oligoethylene glycol) methacrylate (OEGMA) and one of several diarylacene methacrylates, including a tetracene methacrylate and a tetraceneothiophene methacrylate. Exposure to 1O2 in water oxidizes the pendant acenes, resulting in diminution of their fluorescence intensities. The observed rate of oxidation of the tetracene-containing polymers compares favorably with a commercial 1O2-sensitive dye. Polymers that also include energy-donating coumarin side chains show ratiometric fluorescence changes in response to 1O2.
Donor/acceptor-substituted anthradithiophene materials: Synthesis, optical and electrochemical properties
Balandier, Jean-Yves,Quist, Florence,Sebaihi, Noham,Niebel, Claude,Tylleman, Benoit,Boudard, Pol,Bouzakraoui, Said,Lemaur, Vincent,Cornil, Jerome,Lazzaroni, Roberto,Geerts, Yves Henri,Stas, Sara
scheme or table, p. 7156 - 7161 (2011/10/05)
The synthesis and characterization of two new anthradithiophene (ADT) derivatives bearing electron donating (triphenylamine) or accepting (5-formylthiophen-2-yl unit) moieties have been performed to assess their potential as materials for organic photovoltaics. Optical spectroscopy was used to evaluate the effect of electron rich/poor substituents on the visible absorption spectrum and on the stability towards photo-oxidation. The results are interpreted with the assistance of quantum-chemical calculations and cyclic voltammetry experiments.
Tuning a three-component reaction for trapping kinase substrate complexes
Statsuk, Alexander V.,Maly, Dustin J.,Seeliger, Markus A.,Fabian, Miles A.,Biggs, William H.,et al.
supporting information; experimental part, p. 17568 - 17574 (2009/09/08)
The upstream protein kinases responsible for thousands of phosphorylation events in the phosphoproteome remain to be discovered. We developed a three-component chemical reaction which converts the transient noncovalent substrate-kinase complex into a covalently cross-linked product by utilizing a dialdehyde-based cross-linker, 1. Unfortunately, the reaction of 1 with a lysine in the kinase active site and an engineered cysteine on the substrate to form an isoindole cross-linked product could not be performed in the presence of competing cellular proteins due to nonspecific side reactions. In order to more selectively target the cross-linkerto protein kinases in cell lysates, we replaced the weak, kinase- bindi ng adenosine moiety of 1 with a potent protein kinase inhibitor scaffold. In addition, we replaced the o-phthaldialdehyde moiety in 1 with a less-reactive thiophene-2,3-dicarboxaldehyde moiety. The combination of these two structural modifications provides for cross-linking of a cysteine-containing substrate to its corresponding kinase in the presence of competing cellular proteins.
Synthesis, morphology, and field-effect mobility of anthradithiophenes
Laquindanum, Joyce G.,Katz, Howard E.,Lovinger, Andrew J.
, p. 664 - 672 (2007/10/03)
The synthesis, thin-film morphology, and hole mobility in thin-film transistors (TFTs) of compounds based on the novel anthradithiophene (ADT) ring system are reported. The parent compound and its 2,8-dihexyl, didodecyl, and dioctadecyl derivatives (DHADT, DDADT, and DOADT, respectively), synthesized via alkylated thiophene dicarboxaldehyde acetals, were investigated. They all form highly ordered polycrystalline vacuum-evaporated films with mobilities as high as 0.15 cm2/(V s), as high as has ever been observed for a polycrystalline organic material. DOADT has a mobility of 0.06 cm2/(V s) even though 70% of its molecular volume is occupied by hydrocarbon chains. DHADT was cast from solution under atmospheric conditions onto a TFT giving a mobility of 0.01-0.02 cm2/(V s). Thus, the alkylated ADTs combine a pentacene-like intrinsic mobility with greater solubility and oxidative stability.
