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Freeze the dynamicity: charge transfer complexation assisted control over the reaction pathway

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Abstract

Charge transfer (CT) complexes between electron donor and acceptor molecules provide unique alternate D–A arrangements. However, these arrangements cannot be fully translated into chemo-selective organic transformations as the dynamicity of CT complexes in solution results in the co-existence of D–A assemblies and free monomers during the reaction time-scale. A conceptually new strategy to exploit CT complexes toward chemo-selective products by means of seizing the dynamicity of CT complexes is reported here. Aqueous CT complexes of donor and acceptor molecules bearing reactive thiol groups were frozen instantly and cryo-desiccated to get the alternate D–A assemblies intact in the solid state. Oxidation of reactive thiols in an oxygen rich solvent in the solid state resulted in the formation of the hetero-dimer exclusively. CT complexation and appropriate molecular arrangements are the key factors behind successful execution of this novel methodology. The strategy also paves the way to prepare unsymmetrical disulfide molecules from two dissimilar thiols.

Graphical abstract: Freeze the dynamicity: charge transfer complexation assisted control over the reaction pathway

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Publication details

The article was received on 10 Jul 2019, accepted on 06 Sep 2019 and first published on 09 Sep 2019


Article type: Edge Article
DOI: 10.1039/C9SC03417J
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
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    Freeze the dynamicity: charge transfer complexation assisted control over the reaction pathway

    N. Singha, B. K. Das, B. Pramanik, S. Das and D. Das, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03417J

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