Complex chemical systems, such as living organisms, have highly organized structures based on well designed molecules through dynamic interactions. In contrast, synthetic systems exhibit simpler properites. In this talk, I will specifically focus on rational molecular design principles and the utilizations of such principles for the creation of dynamic and complex artificial chemical systems, possesing new functions that cannot be realized by conventional approaches. Owing to the remarkable progress over the past two decades in supramolecualr chemistry, a variety of complex nanostructures can be designed and tailored through thermodynamic control. Despite recent advances, chemical systems under such thermodynamic control are still short of functionality and complexity comparing to living systems. In order to create dynamic and complex chemical systems that surpass our living matters, non-covalent interactions (supramolecular interactions) should be more precisely controlled and have non-equilibriated states. In this regard, this presentation begins with a rational molecular design strategy for the realization of precise non-covalent polymerization in solution[1], [2]. I believe that this achievement steps forward towards dynamic functional chemical systems. From the second part of my talk, a new class of polymer design capable of forming dynamically crosslinked complex network will be discussed[3]. Multiple distinct crosslinking bonds with different bonding strength exist in the network. Such newly observed network realized unsual mechanical properties such as high stretchability, high toughness and autonmous self-healability, whereas their mechanical responses were similar to those of human skin. Lastly, unprecedented applications in electronic systems will be presented using this new energy dissipating chemical system[4],[5]. Integration of the dynamic chemical system with electronic materials successfully imparts its intrinsic dynamicity to electronics such that mechanically tough and self-healable electronic skins are developed for the first time.