The preparation of both postfunctionalizable and chromic poly[3-(N-succinimido-p-phenylcarboxylate(tetraethoxy)oxy)-4-methylthiophene] is reported. The N-hydroxysuccinimide ester side group can easily react with different amine-bearing molecules in the solid state to yield a library of new polythiophene derivatives. The resulting polymers can be dissolved in various solvents, and interactions between the side chains (ligands) and different analytes (targets) can be detected from modifications of both the side-chain and the backbone conformations resulting in important color changes (i.e., affinitychromism). This colorimetric polymeric transducer could therefore lead to highly valuable, versatile, and inexpensive tools for highthroughput screening and drug discovery.