A molecular machine directs the synthesis of a catenane
Data files
Jul 24, 2025 version files 1.83 GB
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NMR_Data.zip
1.83 GB
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README.md
4.24 KB
Abstract
Precise mechanical manipulation of molecules is inherently difficult due to random thermal motion. While directed movement on the molecular scale has been achieved, using it to impose specific, especially energetically disfavored, shapes on molecules and construct mechanically interlocked structures remains a fundamental challenge. Here, we report the synthesis of a catenane enabled by a molecular motor that winds molecular strands into discrete entangled structures, each defined by a specific number of mechanical crossings. Light energy drives unidirectional motor rotation, enabling path-dependent control over a sequence of thermodynamically disfavored yet mechanically distinct and kinetically stable winding states, which are covalently captured and subsequently released to yield a catenane. This machine-directed approach offers a general proof-of-concept strategy for the template-free construction of mechanically interlocked molecules.
Dataset DOI: 10.5061/dryad.nvx0k6f4c
Description of the data and file structure
The repository contains all the raw NMR data that was used for the preparation of the manuscript and supporting material. The main directory contains four folders:
1) The full NMR characterization of all synthesized molecules can be found in "NMR_Compounds".
2) The NMR data of the covalently captured stable helicity winding isomers (Zs)-0, (Es)-1, (Zs)-2, and (Es)-3 can be found in "NMR_Covalent Capture".
3) Diffusion-ordered spectroscopy (DOSY) NMR of the stable helicity winding isomers (Zs)-0, (Es)-1, (Zs)-2, and (Es)-3, the references macrocycles ((Zs)-MM, (Es)-MM, OM) and the catenanes ((Zs)-Catenane and (Es)-Catenane) can be found in "NMR_DOSY".
4) The NMR investigation of the winding mechanism and winding states of machine (Zs)-0 can be found in "NMR_Winding Isomers".
In each main folder, the subfolder of each performed experiment (e.g., NMR_Compounds/S22_Zs-Catenane) can be opened via drag & drop into the MestReNova or TopSpin software.
Files and variables
File: NMR_Data.zip
Description:
Each following bullet point starts with the title of the experiments, followed by a short description of the dataset.
NMR_Compounds:
NMR data of all synthesized molecules (S1-S23) (1H, 13C, COSY, HSQC, HMBC, 19F if applicable)
- "S1_C12DiolTether" to "S23_Es-Catenane" - NMR dataset of the compounds that are presented in the synthesis chapter (chapter 2) of the supporting material
NMR data of the mixtures of (Zs)-MM/OM and (Es)-MM/OM (1H, 19F)
- "(Es)-MM and OM mixture" - 1H and 19F NMR data shown in fig. S28 and S29
- "(Zs)-MM and OM mixture" - 1H and 19F NMR data shown in fig. S28 and S29
NMR_Covalent Capture:
NMR data of the covalently captured winding isomers (Zs)-0, (Es)-1, (Zs)-2, (Es)-3
- "hemz1211-WTO-ZSO" - 1H and 19F NMR data of covalently captured (Zs)-0 isomer shown in fig. S23
- "hemz1212-WTO-ES1" - 1H and 19F NMR data of covalently captured (Es)-1 isomer shown in fig. S23
- "hemz1213-WTO-ZS2" - 1H and 19F NMR data of covalently captured (Zs)-2 isomer shown in fig. S23
- "hemz1214-WTO-ES3" - 1H and 19F NMR data of covalently captured (Es)-3 isomer shown in fig. S23
NMR_DOSY:
1H-DOSY NMR data of the winding isomers (Zs)-0, (Es)-1, (Zs)-2, (Es)-3, the catenanes, and the reference macrocycles (Zs)-MM, (Es)-MM, and OM
- "heWTO-Zs0-DOSY" - DOSY NMR data of (Zs)-0
- "heWTO-Es1-DOSY2" - DOSY NMR data of (Es)-1
- "heWTO-Zs2-DOSY2" - DOSY NMR data of (Zs)-2
- "heWTO-Es3-DOSY2" - DOSY NMR data of (Es)-3
- "heWTO-ZsCat-DOSY" - DOSY NMR data of (Zs)-Catenane shown in fig. S35
- "heWTO-EsCat-DOSY" - DOSY NMR data of (Es)-Catenane shown in fig. S36
- "heWTO-226-E-DOSY" - DOSY NMR data of (Es)-MM shown in fig. S34
- "heWTO-226-z" - DOSY NMR data of (Zs)-MM shown in fig. S33
- "heWTO-243-DOSY" - DOSY NMR data of OM shown in fig. S32
NMR_Winding Isomers:
NMR data for winding sequence of (Zs)-0 (1H, 19F)
- "20C Winding Sequence 19F" - shown in fig. S4
- "40C Winding Sequence 1H" - shown in fig. S3
- "-30C Winding Sequence 19F" - shown in fig. S5
NMR data for rotational cycle of benzoylated (Zs)-MM (1H)
- "(Zs)-MM Rotational Cycle" - 1H NMR data of the 360° rotational cycle of benzoylated motor macrocycle (Zs)-MM/S20 shown in fig. S15
NMR data of winding isomers (Zs)-0, (Es)-1, (Zs)-2, (Es)-3 (1H, 13C, COSY, HSQC, HMBC, ROESY)
- "Zs-0" - 1D and 2D NMR characterization of (Zs)-0, ROESY shown in fig. S19
- "Es-1" - 1D and 2D NMR characterization of (Es)-1, ROESY shown in fig. S21
- "Zs-2" - 1D and 2D NMR characterization of (Zs)-2, ROESY shown in fig. S20
- "Es-3" - 1D and 2D NMR characterization of (Es)-3, ROESY shown in fig. S22
- "Es-3 and Zm-4 at -10C and 40C" - 1H NMR data of (Es)-3 and (Zm)-4 at -10 °C and 40 °C shown in fig. S12 and S13
VT-NMR experiment of (Es)-3 (1H)
- "Es-3 VT Experiment" - 1H NMR data of (Es)-3 from -10 °C to 80 °C shown in fig. S14
Code/software
The NMR data were evaluated with MestReNova Version 11.0.4-18998 or TopSpin Version 4.5.0.
Access information
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