The structure and substitution pattern of the side chains of polymers affect polymer-chain behaviors in solution and physical properties in the solid state. As a part of our studies on ladder polymers with two-dimensional conformational freedom, here we synthesize symmetrical or unsymmetrical diazacyclooctane(DACO)-containing flexible ladder polymers with various functionalities through sequential N-alkylation reactions for a Tröger's base-containing rigid ladder polymer.