This thesis describes the preparation and characterisation of a number of homochiral coordination and metallosupramolecular assemblies. These species were formed from the reaction of chiral pyridine and quinoline containing ligands and metal ions. The combination of traditional coordination chemistry and supramolecular interactions led to a range of polymeric and network structures being formed. The ligands used in this thesis can be divided into two broad categories: alkaloids and ligands derived from them, and amino acid-based ligands. In the first category three new ligands were synthesized, and a variety of routes towards alkaloid-based homochiral ligands were investigated. The second category focused on three ligand motifs, and resulted in the preparation of 16 ligands. These two categories of ligands were reacted with a range of metal salts to investigate their coordination and supramolecular chemistry. The structure of twenty complexes was determined by single crystal X-ray crystallography. The complexes had a range of structures, with discrete and polymeric species being formed. Hydrogen bonding was an important feature in the supramolecular chemistry of the complexes, playing a different role in different series of complexes. Two chiral coordination polymers and one chiral coordination network were synthesized. All three of these structures possessed directionality to some degree: in the coordination network and one of the polymers the directionality is counterbalanced by the opposite directionality being present in the crystal, while the second coordination polymer is generated by the screw axis present and has a high degree of overall directionality.