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
    License
    Creative Commons Attribution 4.0 International
Publication date22/07/2020
Retention date25/07/2030
accessLevelPublicAccess levelPublic
SensitivityUndefined
duaNoneContract on the use of data
Contributors
  • Li, Haidong
  • Duwald, Romain orcid
  • Pascal, Simon orcid
  • Voci, Silvia
  • Besnard, Céline orcid
  • Bosson, Johann orcid
  • Bouffier, Laurent
  • Lacour, Jérôme orcid
  • Sojic, Neso
14
0
  • Quality (0 Reviews)
  • Usefulness (0 Reviews)

Datacite metadata

Packages information

Similar archives

Laboratory of Professor Jérôme Lacour
Dataset of Organic & Biomolecular Chemistry_Aliphatic amide macrocycles
2019 accessLevelPublic Public 1.6 GB
Laboratory of Professor Jérôme Lacour
Dataset of submission_Photo-Induced Thiol-Ene Reactions of Unsaturated Polyether Macrocycles
2019 accessLevelPublic Public 1016.2 MB
Laboratory of Professor Jérôme Lacour
Multistate Aggregation-Induced Chiroptical Properties of Enantiopure Disulfide-Mediated BisPyrene Macrocycles
2022 accessLevelPublic Public 151.2 MB
Laboratory of Professor Jérôme Lacour
Regiodivergent Synthesis of Oxadiazocines via Dirhodium-Catalyzed Reactivity of Oxazolidines and alpha-Imino Carbenes
2023 accessLevelPublic Public 1.1 GB
All rights reserved by DLCM and the University of GenevaunigeBlack