Large Azobenzene Macrocycles: Formation and Detection by NMR and MS Methods

Helena Roithmeyer, Merle Uudsemaa, Aleksander Trummal, Mari-Liis Brük, Sebastian Krämer, Indrek Reile, Vitālijs Rjabovs, Kirsti Palmi, Matt Rammo, Riina Aav, Elina Kalenius, Jasper Adamson

S 2 Contents General Information ................................ ................................ ................................ ................................ ........... S 4 Methods ................................ ................................ ................................ ................................ ................................ . S 4 Purification ................................ ................................ ................................ ................................ ............. S 4 NMR Studies ................................ ................................ ................................ ................................ .......... S 4 2D DOSY NMR ................................ ................................ ................................ ................................ ..... S 4 External Standard and calibration for DOSY NMR ................................ ................................ ............... S 5 Illustrative 2D DOSY plots ................................ ................................ ................................ .................... S 5 DOSY characterization ................................ ................................ ................................ ........................... S 6 Mass spectrometry (ESI - MS) and ion mobility mass spectrometry (IM - MS) ................................ ........ S 8 Reaction Method A ................................ ................................ ................................ ................................ ........... S 11 Synthetic procedure for A: One pot reaction ................................ ................................ ........................ S 11 Reaction monitoring of the reaction A with different base equivalents ................................ ............... S 11 Characterization of the work up mixtures obtained from A ................................ ................................ . S 11 NMR spectra and ESI - MS analysis from reaction A ................................ ................................ ............ S 12 R eaction Method B ................................ ................................ ................................ ................................ ............ S 20 Synthetic procedure of the reaction B: Dropping one reactant (1) ................................ ....................... S 21 Characterization of the work up mixtures obtained from B ................................ ................................ . S 20 NMR spectra and analysis from reaction B ................................ ................................ .......................... S 21 Reaction Method C ................................ ................................ ................................ ................................ ........... S 27 Synthetic procedure for C: Dropping both reactants (1 and 2) ................................ ............................. S 27 Reaction monitoring of the reaction C with different base equivalents ................................ ................ S 27 Characterization of the work up mixtures obtained from C ................................ ................................ . S 27 NMR spectra and analysis from reaction C ................................ ................................ .......................... S 28 Reaction Method D ................................ ................................ ................................ ................................ ........... S 35 Synthetic procedure for D: One pot reaction and reflux ................................ ................................ ....... S 35 Reaction monitoring of the reaction D with different base equivalents ................................ ............... S 35 Characterization of the work up mixtures obtained from D ................................ ................................ . S 36 NMR spectra and analysis from reaction D ................................ ................................ .......................... S 36 Reaction Method E ................................ ................................ ................................ ................................ ............ S 42 Synthetic procedure for E: Dropping both reactants (1 and 2) and refluxing ................................ ....... S 42 Reaction monitoring of the reaction E with different base equivalents ................................ ................ S 42 Characterization of the work up mixtures obtained from E ................................ ................................ .. S 4

Date
03.07.2023.
Keywords
Large Azobenzene Macrocycles: Formation and Detection by NMR and MS Methods
Hyperlink
https://www.tandfonline.com/doi/suppl/10.1080/10610278.2023.2230334?scroll=top