Syntheses of shuttlecock- and bowl-equipped phenylazopyridines and photomodulation of their coordination ability to Zn-porphyrin

Shuttlecock- and bowl-equipped 4-(phenylazo)pyridine derivatives, which bear substituents that allow the pyridine moiety to protrude in the trans form but hinder it in the cis form, have been designed and synthesized. These molecules show cis/trans photoisomerization despite the presence of bulky substituents. H-1 NMR titration with Zn-porphyrin showed that the trans isomers coordinate to Zn-porphyrin much stronger than the cis isomers. (c) 2009 Elsevier Ltd. All rights reserved.