Soft materials comprising π-conjugated molecules are a fundamental class of materials that support organic electronics and optical technologies. The electronic and optical properties of π-conjugated molecules strongly depend on their molecular orientation and modes of assembly, meaning that different packing structures can lead to distinct functions. Therefore, in addition to extending the intrinsic functions of individual π-conjugated molecules, the development of these π-systems critically relies on controlling molecular orientation and organization to create functional molecular assemblies. However, the synthetic complexity required for functionalization and controlled assembly of π-conjugated molecules has become a major bottleneck in the development of π-electronic materials. To address this issue, the researcher focuses on developing simple and efficient routes to π-systems and exploring their novel functions, leveraging original molecular designs and organic synthesis strategies based on atom-economical chemical reactions.