Photoinduced symmetry-breaking charge separation (SB-CS) is a fundamental process in molecular photophysics that governs energy and charge transport in reaction centers, organic semiconductors, supramolecular assemblies and hybrid materials.1 However, identifying molecular architectures that efficiently promote SB-CS remains a key challenge. Cross-architectures exhibiting minimal excitonic coupling have attracted considerable interest due to their distinctive chromophore arrangements and emergent photophysical properties.2 Herein, we propose a cross-architecture as a promising platform for SB-CS3-5 and employ data-driven models to correlate molecular structure with SB-CS dynamics, providing a framework for the rational design of next-generation optoelectronic and energy-conversion materials