Studies of gas phase ion-neutral reactions provide insight into many areas of astrochemistry, including the elusive characterization of the Diffuse Interstellar Bands (DIBs). This presentation gives an overview of our experimental studies of several classes of positive and negative ions, using the flowing afterglow-selected ion flow tube and a newly modified ion trap. Earlier studies of carbon chain anions and polycyclic aromatic hydrocarbon (PAH) cations, both of which have been suggested as carriers of the DIBs, are described. More recent work including isomeric PAHs, nitrogen-containing PAHs, negative ions of PAHs, and negative ions of 5-membered heterocyclic rings are discussed. Finally, the study of quantitative thermochemistry by coupling our results with data from Photoelectron Spectroscopy is described.