Dataset of Regioselective sulfonation of diaza [4] and [6]helicene dyes for far-red electrochemiluminescence in water

There is a very rapid development of new organic electrochemiluminescence (ECL) dyes with a large variety of electronic properties enabled by playing with structural variations achieved by organic chemistry. However, a major limitation is their water solubility while keeping their ECL capabilities. Here, the synthesis and optical, electrochemical and ECL properties of a series of four original water-soluble helicene dyes operating in physiological conditions are reported. Those species were prepared using diaza [4] and [6]helicenes as structural cores functionalized for the purpose of this study with sulfonate groups in various positions, which significantly improves their water solubility. Synthetically, thanks to strongly acidic conditions, regioselective sulfonylation reactions were enabled and occurred at defined position(s) of the outer rim of the helical cores. In terms of optical properties, such functional groups induce a red-shift of the absorption and emission properties up to the near-infrared in the [4]helicene series. The fluorescence ranges typically in the red to far-red (660-710 nm) and spanning towards the near-infrared region. The electrochemical characterization evidenced an irreversible oxidation, whereas the reduction could be reversible depending on the dye. This series of molecules were investigated as ECL emitters in aqueous media using tri-n-propylamine as a sacrificial co-reactant and revealed to be efficient ECL luminophores in these conditions. Such a study on these water-soluble π-conjugated dyes presenting different core structures may guide the design and analytical applications of new ECL dyes with a strong efficiency in physiological conditions.

Organizational unit

Laboratory of Professor Jérôme Lacour

Type

Dataset

DOI

10.26037/yareta:myh2q7xjavcs7im2bu3budlqk4

Type

general.label.dataset

License

Creative Commons Attribution 4.0 International