Synthesis of monomers is the primary focus of this dissertation. The overall objectives include: (i) to design naphthalene diimide (NDI)-based chromophores with different electrochromic properties and (ii) to design crosslinkable tetraphenylbenzidine based chromophores for use in electrochromic devices (ECDs). The synthesis of NDI based chromophores including DPy-N4-NDI, DPy-N3-NDI and DPy-N2-NDI were achieved by direct imidization using NTDA and propriate choice of amino pyridines. Pyridine modified NDIs are further reacted with 1-iodomethane and 6-bromohexane to form DM-N2-NDI2I, DM-N3-NDI2I, DM-N4-NDI2I, DH-N3-NDI2Br and DH-N4-NDI2Br. All chromophores exhibit reversible color change from pale yellow, to brown, then dark green with different operational voltage ranging from -12mV to -134 mV for the first reduction and -334 mV to -598 mV for the second reduction. Indole was introduced to TPB as the cross-linkable group for solution processible TPB. Two synthetic routes were involved, to generate branched indole TPB and fused indole TPB.