Selectivity in tip-induced skeletal editing via heteroatom substitution
Abstract
Skeletal editing enables precise structural modifications of molecules at late stages of a synthetic sequence, with applications in drug discovery and materials science. We recently demonstrated skeletal editing on the single-molecule scale. Voltage pulses applied by the tip of a scanning probe microscope to an oxygen-containing seven-membered heterocycle led to both oxygen deletion and ring-contraction rearrangement reactions. An open question is whether selective skeletal editing of a heterocyclic core can be achieved by an appropriate choice of the heteroatom. Here, we show that tip-induced reactions of an analogous sulfur-containing seven-membered ring results in sulfur deletion in virtually all cases. Our results demonstrate that the combination of tip-induced chemistry and heteroatom selection in the molecular design is a powerful strategy for single-molecule skeletal editing, with the potential to enable diverse structural transformations of heterocyclic frameworks.
Versions
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BibTeX
@misc{mishra2026selectivity,
title = {{Selectivity in tip-induced skeletal editing via heteroatom substitution}},
author = {Shantanu Mishra and Rasmus Svensson and Valentina Malave and Florian Albrecht and Manuel Vilas-Varela and Henrik Grönbeck and Leo Gross and Diego Peña},
howpublished = {arXiv},
year = {2026},
month = jun,
doi = {10.48550/arxiv.2606.22677},
eprint = {2606.22677},
archivePrefix = {arXiv},
url = {https://arxiv.org/abs/2606.22677},
note = {CC BY 4.0},
}
RIS
TY - UNPB
TI - Selectivity in tip-induced skeletal editing via heteroatom substitution
AU - Shantanu Mishra
AU - Rasmus Svensson
AU - Valentina Malave
AU - Florian Albrecht
AU - Manuel Vilas-Varela
AU - Henrik Grönbeck
AU - Leo Gross
AU - Diego Peña
PY - 2026
DA - 2026/06/21
PB - arXiv
DO - 10.48550/arxiv.2606.22677
UR - https://arxiv.org/abs/2606.22677
AB - Skeletal editing enables precise structural modifications of molecules at late stages of a synthetic sequence, with applications in drug discovery and materials science. We recently demonstrated skeletal editing on the single-molecule scale. Voltage pulses applied by the tip of a scanning probe microscope to an oxygen-containing seven-membered heterocycle led to both oxygen deletion and ring-contraction rearrangement reactions. An open question is whether selective skeletal editing of a heterocyclic core can be achieved by an appropriate choice of the heteroatom. Here, we show that tip-induced reactions of an analogous sulfur-containing seven-membered ring results in sulfur deletion in virtually all cases. Our results demonstrate that the combination of tip-induced chemistry and heteroatom selection in the molecular design is a powerful strategy for single-molecule skeletal editing, with the potential to enable diverse structural transformations of heterocyclic frameworks.
ER -