Synthesis and fluorescence properties of 4-diarylmethylene analogues of the green fluorescent protein chromophore

Locking the GFP Fluorophore to Enhance Its Emission Intensity

“…Nevertheless, GFPc 7 presents AIEE properties in the solid state and in frozen solution, due to the restrictions of molecular motions. The crystal packing of GFPc 7a revealed intermolecular π-π interactions, responsible for the quenched fluorescence [21]. Looking at these examples, we can conclude that many GFPc analogues present AIEE properties and are brightly emissive in the solid state.…”

Synthesis and properties of 4-(diarylmethylene)imidazolinone-conjugated fluorescent nucleic acids

“…2). 19,20 This result indicates that the fluorescent property of DAINs is maintained in dC DAIN nucleoside 5, which prompted us to use dC DAIN in fluorescent ONs for the monitoring of nucleic acid structure changes.…”

“…To simplify the HBI fluorescent mechanism, we developed 4-(diarylmethylene)imidazolinones (DAINs) that contain two aryl groups in the double bond. 19,20 DAINs have a combination of the Z-and E-forms of the benzylidene moiety, and exhibit fluorescence when their molecular motions are suppressed, such as the free rotation of the aryl-alkene single bond and double-bond isomerization. Interestingly, DAINs show fluorescence in the solid and frozen solution states but not in solution state.…”

Electrochemical Trifluoromethylation/Bicyclization of N-Cyanamide Alkenes: Synthesis of Bicyclic Amidine Derivatives

“…Given our continuous interest in the development of sustainable and efficient processes for preparing aza-heterocyclic skeletons by using nitriles as C−N building blocks in an atom-economic fashion, 3cd8 we envision that an anodically oxidizing trifluoromethylation cascade of N-cyanamide alkene bearing two electronically differentiated olefin moieties would be feasible (Scheme 1b), 9,10 in which the addition of a CF 3 radical generated from Langlois' reagent (CF 3 SO 2 Na) to an electronic-rich alkene moiety, followed by nitrile insertion and subsequent cyclization of the resulting nucleophilic iminyl radical species with another electronic-deficient alkenyl unit, could afford functionalized trifluoromethylated bicyclic amidines (Scheme 1c). 11 Furthermore, the ready availability and manipulation of reaction partners (CF 3 SO 2 Na and Nunsaturated acyl cyanamide alkenes) and facile CF 3 incorporation would enable this oxidant-free electrochemical process to be an appealing complement for the preparation of nonaromatic fused azaheterobicyclic compounds in a highly efficient and sustainable manner. Herein, we report these results.…”