Synthesis of rigid photoswitchable hemithioindigo ω-amino acids

The synthesis of novel N-Boc- and N-Fmoc protected hemithioindigo-based ω-amino acids is described. An approach to modulate the thermal stability of a hemithioindigo subunit is presented. Placing the amino-group in the stilbene part from the para- to meta-position leads to an increase of the half-life of the thermally labile E-form from 19 h to 47 h.