Recent developments in hybrid electro-optic (EO) systems, in which an organic material with an ultra-large second-order susceptibility is combined with silicon (SOH) or gold (POH) waveguides at the nanoscale. Tight confinement of the optical and RF fields in such devices has enabled operating frequencies > 300 GHz and voltage-length parameters (UπL) < 40 V-μm with existing high-performance organic electro-optic (OEO) materials. However, achieving UπL values on the order of 1 V-μm will require a new generation of OEO materials. The short path lengths within hybrid devices greatly alleviate concerns about optical loss, enabling development of OEO chromophores with extraordinarily large hyperpolarizabilities and refractive indices at telecom wavelengths. However, as device dimensions shrink, chromophore-surface interactions, space-efficiency, and refractive index anisotropy become more critical. Practical device implementations also require materials with high thermal and chemical stability and uncompromising EO performance. We have used a theory-aided design process applying classical and quantum mechanical techniques to design a new generation of OEO materials intended to meet the needs of hybrid devices. We have synthesized these materials, characterized their hyperpolarizability by hyper-Rayleigh scattering, and evaluated their bulk electro-optic behavior and prospects for implementation in nanoscale devices.