Supramolecular Structures Based on Bis(2-hydroxy-5-chlorophenyl) Sulfide and Spirobicromane with Bipyridines

Six new supramolecular structures have been prepared by bis(2-hydroxy-5-chlorophenyl) sulfide (HCS) and/or spirobicromane (SBC) with bipyridine bases 4,4‘-bipyridyl (bipy), 1,2-di(4-pyridyl)ethylene (dipy-ete), 1,2-bis(4-pyridyl)ethane (bipy-eta), and 4,4‘-dipyridyl N,N‘-dioxide (dipy-dox). These molecular complexes are (HCS)·(bipy) 1, (HCS)·(dipy-ete) 2, (HCS)·(bipy-eta) 3, (HCS)·(dipy-dox) 4, (SBC)·(dipy-ete) 5, and (SBC)·(dipy-dox)·H2O 6, respectively. The crystal structures of 16 have been determined by single crystal X-ray diffraction. All of these molecular complexes exhibit supramolecular structures via O−H···N or O−H···O hydrogen bondings. Both 1 and 2 form interestingly [2 + 2] macrocyclic structures, whose sizes are ca. 12.495(6) Å × 5.087(6) Å and 14.774(6) Å × 5.300(6) Å, respectively. Compounds 3 and 5 form one-dimensional zigzag chain structures. Compounds 4 and 6 form two-dimensional double helices. These results demonstrate that by changing the guest molecule, we can obtain different hydrogen-bonded supramolecular structures through different interactions.