288627-04-3Relevant academic research and scientific papers
Influence of molecular structure on the antimicrobial function of phenylenevinylene conjugated oligoelectrolytes
Yan, Hengjing,Rengert, Zachary D.,Thomas, Alexander W.,Rehermann, Carolin,Hinks, Jamie,Bazan, Guillermo C.
, p. 5714 - 5722 (2016)
Conjugated oligoelectrolytes (COEs) with phenylenevinylene (PV) repeat units are known to spontaneously intercalate into cell membranes. Twelve COEs, including seven structures reported here for the first time, were investigated for the relationship betwe
Polyfluorinated bis-styrylbenzene β-amyloid plaque binding ligands
Flaherty, Daniel P.,Walsh, Shannon M.,Kiyota, Tomomi,Dong, Yuxiang,Ikezu, Tsuneya,Vennerstrom, Jonathan L.
, p. 4986 - 4992 (2007)
β-Amyloid (Aβ) binding affinities and specificities for six bis-styrylbenzenes with multiple magnetically equivalent fluorine atoms in the form of a tetrafluorophenyl core or symmetrical trifluoromethyl and trifluoromethoxy groups were determined by means of fluorescence titrations with amyloid peptide Aβ1-40 and a novel in vitro fluorescence-based assay using APP/PS1 transgenic mouse brain sections. Bisstyrylbenzenes with a tetrafluorophenyl core had increased Aβ binding affinities compared to their monofluorophenyl or phenyl counterparts. Bis-styrylbenzenes with carboxylic acid functional groups had lower Aβ binding affinities than their neutral counterparts. Selected bis-styrylbenzenes were demonstrated to have good blood - brain barrier penetration capabilities. These data extend the SAR of bis-styrylbenzene Aβ binding and provide direction for the development of a noninvasive probe for early detection of Alzheimer's disease using 19F MRI.
Hydrophilic Conjugated Polymers Prepared by Aqueous Horner-Wadsworth-Emmons Coupling
Page, Zachariah A.,Liu, Yao,Puodziukynaite, Egle,Russell, Thomas P.,Emrick, Todd
, p. 2526 - 2532 (2016)
The synthesis of hydrophilic conjugated polymers typically relies on organometallic coupling methodologies. Here we present an approach to prepare polar poly(arylene-vinylene)s (PAVs) in water using the Horner-Wadsworth-Emmons (HWE) reaction. The additional preparation of discrete arylene vinylene (AVs) afforded insight into HWE kinetics and regioselectivity. Nine novel PAVs and AVs were synthesized, characterized by UV-vis absorption and ultraviolet photoelectron spectroscopy, and studied for their utility in sensing and photovoltaic applications.
Quadrupolar fluorophores with tetrafluorobenzene central electron acceptor
Kulhánek, Ji?í,Klikar, Milan,Pytela, Old?ich,Almonasy, Numan,Tydlitát, Ji?í,Bure?, Filip
, (2021/02/16)
Seven novel quadrupolar chromophores based on 1,2,4,5-tetrafluorobenzene (TFB) central electron acceptor unit and methoxythiophene peripheral donor were synthetized and described. Fundamental structure-property relationships were elucidated via thermal, e
Intimately bound coumarin and bis(alkylaminostyryl)benzene fragments: Synthesis and energy transfer
Cavazzini, Marco,Quici, Silvio,Orlandi, Simonetta,Sissa, Cristina,Terenziani, Francesca,Painelli, Anna
, p. 2827 - 2833 (2013/04/10)
A novel trichromophoric assembly was synthesized, where two molecules of 7-alkoxy-4-methylcoumarin, acting as energy donors, were linked at a fixed distance and controlled geometry to an energy-acceptor bis(alkylaminostyryl) unit. Resonance energy transfe
Fluorinated molecules relevant to conducting polymer research
Krebs, Frederik C.,Jensen, Thomas
, p. 77 - 84 (2007/10/03)
The synthesis of versatile fluorine compounds for conducting polymer research on fluorinated materials is presented. 1,2,4,5-Tetrafluorobenzene was converted to 1,2,4,5-tetrafluorobenzaldehyde (1) and protected as an acetal. This gave the acetals 1,2,4,5-tetrafluoro-3-(1,3-dioxol-2-yl)benzene (2a) and 1,2,4,5-tetrafluoro-3-(5,5-dimethyl-1,3-dioxan-2-yl)benzene (2b). Compounds 2a and 2b were converted into the semiprotected 2,3,5,6-tetrafluoroterephthaldehydes: 1,2,4,5-tetrafluoro-3-(1,3-dioxol-2-yl)-6-formylbenzene (3a) and 1,2,4,5- tetrafluoro-3-(5,5-dimethyl-1,3-dioxan-2-yl)-6-formylbenzene (3b). While 3a was easily deprotected to give 2,3,5,6-tetrafluoroterephthaldehyde (4) compound 3b proved very resilient to hydrolysis and gave a 1:1 mixture of 4 and 1,2,4,5-tetrafluoro-3,6-bis(5,5-dimethyl-1,3-dioxan-2-yl)benzene (5). Compound 4 was reduced to 1,2,4,5-tetrafluoro-3,6-dihydroxymethylbenzene (6) and converted into 1,2,4,5-tetrafluoro-3,6-dibromomethylbenzene (7). Compound 7 was finally converted into 1,2,4,5-tetrafluoro-3,6-bis(diethylphosponylmethyl)benzene (8). Compounds 4 and 8 are versatile fluorinated molecules that can be used to replace their hydrogen counterparts in many molecules and materials. To illustrate this compounds 4 and 8 were oligomerised to give partially fluorinated polyphenylenevinylene (9).
