No abstract

A new family of oligo(phenylene ethynylene) (OPE) glucosides has been prepared and characterized. Our results demonstrate that fine-tuning of their photophysical properties can be obtained by acting on the electronics of the core and molecular skeleton. Modulation of the hydrophobic chain length and substituents on the central moieties influences the bioaffinity too. In particular, introducing a NMe2 group on the aromatic central core affords a highly efficient biocompatible fluorescent probe that can be taken up in cytoplasmic vesicles of HEp-2 cells (cells from epidermoid carcinoma larynx tissue). The photophysical behavior, high quantum yield, and stability open the way to the use of the OPE family as stains for cellular imaging analysis by fluorescence microscopy.

The stereoselective and efficient monoaddition of transient [(1S,2R,4R)‐2‐hydroxy‐7,7‐dimethylbicyclo[2.2.1]hept‐1‐yl]methanesulfenic (=(1S)‐isoborneol‐10‐sulfenic) acid to isomeric diethynylbenzenes affords {1‐[(1S)‐isoborneol‐10‐sulfinyl]ethenyl}ethynylbenzenes. Their enantiomerically pure (RS)‐epimers are involved in a Cu‐free Sonogashira coupling with 1,4‐diiodo‐2,5‐dimethoxybenzene to give C2‐symmetric bis‐sulfinyl phenylene ethynylenes, stimulating prototypes of new sulfurated chiral architectures that can find application as chelating agents.