Non-covalent interactions and reactivity of sulfur-rich birhodanine-based acceptors

Abstract

A diverse library of π-conjugated electron acceptors is essential for the rational design of molecular materials with tunable electronic properties. In this context, the development of structurally related acceptors, including 3,3′-dialkyl-5,5′-bithiazolidinylidene-2,2′-dione-4,4′-dithiones ( OS- R ), their isomers 3,3′-dialkyl-5,5′-bithiazolidinylidene-4,4′-dione-2,2′-dithiones ( SO- R ), and their sulfur analogues 3,3′-dialkyl-5,5′-bithiazolidinylidene-2,4,2′,4′-tetrathiones ( SS- R ), with adjustable redox properties remains a key objective. In the present study, we focus on the intrinsic reactivity of these acceptor cores to deliberately tune their redox behavior. The resulting compounds were structurally characterized. Moreover, iodine atoms were incorporated into the acceptor framework to induce halogen bonding interactions, which were confirmed by X-ray diffraction analyses in both the synthetic precursors and the corresponding acceptors.

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Cite

BibTeX RIS

BibTeX

@article{gal2026noncovalent,
  title = {{Non-covalent interactions and reactivity of sulfur-rich birhodanine-based acceptors}},
  author = {Yann Le Gal and Azilis Desaize and Hugo Bevan and Thierry Roisnel and Vincent Dorcet and Dominique Lorcy},
  journal = {Tetrahedron},
  year = {2026},
  month = sep,
  doi = {10.1016/j.tet.2026.135402},
  url = {https://hal.science/hal-05767878v1},
  note = {CC BY},
}

RIS

TY  - JOUR
TI  - Non-covalent interactions and reactivity of sulfur-rich birhodanine-based acceptors
AU  - Yann Le Gal
AU  - Azilis Desaize
AU  - Hugo Bevan
AU  - Thierry Roisnel
AU  - Vincent Dorcet
AU  - Dominique Lorcy
PY  - 2026
DA  - 2026/09/28
JO  - Tetrahedron
DO  - 10.1016/j.tet.2026.135402
UR  - https://hal.science/hal-05767878v1
AB  - A diverse library of π-conjugated electron acceptors is essential for the rational design of molecular materials with tunable electronic properties. In this context, the development of structurally related acceptors, including 3,3′-dialkyl-5,5′-bithiazolidinylidene-2,2′-dione-4,4′-dithiones ( OS- R ), their isomers 3,3′-dialkyl-5,5′-bithiazolidinylidene-4,4′-dione-2,2′-dithiones ( SO- R ), and their sulfur analogues 3,3′-dialkyl-5,5′-bithiazolidinylidene-2,4,2′,4′-tetrathiones ( SS- R ), with adjustable redox properties remains a key objective. In the present study, we focus on the intrinsic reactivity of these acceptor cores to deliberately tune their redox behavior. The resulting compounds were structurally characterized. Moreover, iodine atoms were incorporated into the acceptor framework to induce halogen bonding interactions, which were confirmed by X-ray diffraction analyses in both the synthetic precursors and the corresponding acceptors.
SN  - 0040-4020
ER  -

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