Two bola-amphiphilic small molecules, based on the diphenylanthracene skeleton structure, namely, BASM-1 and its functionalized small molecule BASM-2, were designed and synthesized. The self-assembly behavior and mechanism of these two molecules in aqueous solution were studied. The supramolecular two-dimensional (2D) layer and the covalent 2D polymers were, respectively, prepared by these two molecules. What is more, the transverse size of the covalent 2D polymer laminates increased with the extension of the polymerization time. Atomic force microscopy results showed that both free-standing single-layer 2D polymers and few layer laminates with two to three molecular layers were obtained. So our work provides a simple and efficient method for directly preparing independent both supramolecular 2D polymers and covalent 2D polymers in liquid phase which is of great significance. (c) 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 1748-1755