We prepared four types of red-shift phthalocyanines: 2,9,16,23-tetra(hetp-t-1 -enyl) phthalocyanine; 2,9,16,23-tetrachloro-3,10,17,24-tetra(3-methoxypro1p --y nyl) phthalocyanine; 3,4,12,13,2 1,22,30,3 l-octa(alkyny1) and octa(alkeny1) naphthalocyanines. It was found that the each conjugated alkenyl group causes about 3nm red-shift on the PC Q-band. We also demonstrated the n-conjugation of Ncs lead to a 3.5 - 4 nm red-shift for each alkynyl and a 3.5 nm red-shift for each alkenyl on the Q-bands. In this thesis we also prepared the unsymmetrical substituted Pcs via both solidsupport synthesis and liquid phase synthesis. Size-exclusion separation was used in the purification for the target Pc. The one-step bromination to prepare 4-bromophthalonitrile was reported to produce a mixture containing up to three products, we found controlling the stiochiometric ratio of phthalonitrile to dibromoisocyanuric acid could give single product: 4-bromophthalonitrile in 3 3% yield. In chapter 7, we introduced the preparations of benzimidazole-chloroquinoline complexes, a type of candidates for antimalaria and anti-HIV.