Dataset for Synthesis, Resolution, Configurational Stability and Properties of Cationic Functionalized [5]helicenes

A straightforward approach to the synthesis of two different series of cationic [5]helicenes has been achieved including, in dioxa series, the possibility to introduce aromatic functional groups at the periphery of the helical structure. While photo-physical study highlights that the introduction of aryl substituents at position 23 of the helical moieties has a negligible impact on the optical properties, styryl substituents allow a welcoming extension of the conjugation pathways. Finally, a red-shift of the optical properties was evidenced upon introduction of nitrogen atoms in the helicene scaffold, leading to particularly good fluorescence efficiencies in the red domain for a helicenic dye. Detailed information on racemization kinetics was collected for the most stable species upon direct HPLC resolution or, when configurational lability was too high, through VT-HPLC analysis on chiral stationary phase (ΔG‡ values ranging from 20.3 to 32.8 kcal.mol-1 and above)

    Organizational unit
    Laboratory of Professor Jérôme Lacour
    Type
    Dataset
    DOI
    10.26037/yareta:jbrucdsj5nentl4mjqehwtcycu
    License
    Creative Commons Attribution 4.0 International
Publication date14/07/2020
Retention date24/08/2030
accessLevelPublicAccess levelPublic
SensitivityUndefined
duaNoneContract on the use of data
Contributors
  • Marinova, Maya orcid
  • Pascal, Simon orcid
  • Besnard, Céline orcid
  • Guénée, Laure
  • Shivachev, Boris orcid
  • Kostova, Kalina orcid
  • Villani, Claudio orcid
  • Franzini, Roberta orcid
  • Dimitrov, Vladimir orcid
  • Lacour, Jérôme orcid
12
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