Directed self-assembly has been used to create micro-nano scale patterns, including chiral periodic structures of organic molecules, for potential applications in optics, photonics, metamaterials, and medical and sensing technologies. This study presents a straightforward approach for fabricating large-scale chiral grating porphyrin assemblies through template-assisted techniques. The solution of tetrakis(4-sulfonatophenyl)porphyrin (TPPS) was induced by chiral amino acids (l/d-arginine and l/d-serine) to self-assemble into highly ordered chiral grating structures with the assistance of sodium dodecyl sulfate (SDS). The structures show precise line widths (5.5 µm) and gaps (18 µm). Using in situ optical microscopy and second harmonic generation (SHG) microscopy, the chiral characteristics and dynamic evolution of the template-assisted self-assembly are investigated. It is found that the chirality of amino acids induced TPPS self-assembled into chiral structures and the liquid contraction interface significantly enhanced the chirality of the assemblies. This study is significant for understanding the mechanism of chiral evolution and designing novel micro-nano materials with predetermined chiral properties.