The synthesis of inherently ductile epoxy network as measured by their resistance to deformation however is less reported and is the subject of this study. Common strategies have been to incorporate structures that are inherently rigid, [8] such as liquid crystalline [9,10] or highly aromatic, [11,12] while others have sought to build a combination of both rigid and flexible features into a network. [13][14][15] Highly aromatic structures will generally have excellent mechanical and thermal properties and resistance to solvent ingress, but are also notoriously difficult to process. As a result, the following studies are a reflection of the variety of strategies attempting to break this paradigm. Karimata et al. (2016) [16] synthesized a tri-aryl di-epoxide monomer linked by flexible carbosilane segments. After curing with an aromatic amine, the glass transition temperature (T g ) of the network was still below room temperature, suggesting potential application as a reactive flexibilizer. Wan et al. (2016) [17] synthesized a bioderived eugenol epoxy resin, essentially a tri-aryl ether linked epoxy resin with a superior modulus, hardness, and char yield compared with a related epoxy amine cured network. It also had a higher creep displacement attributed to increased chain mobility in the glassy state. Yu et al. (2018) [18] combined a rigid carboxamide structure with flexible aliphatic ethers to synthesize an amine, which when cured with an epoxy resin reported improvements in tensile strength, failure strain, and impact strength without any commensurate deterioration in flexural strength. Varley et al. (2019) synthesized highly aromatic ether-linked epoxy monomers and amines, exploring the impact of substitution patterns on the properties and processability. [19] Improvements in yield and failure strain, referred to as distortional behavior, were attributed to an increase in energy dissipated through phenylene rotations available to para-substituted amine or epoxy resins. [20,21] In this work, two tri-aryl epoxy resins containing flexible methylene linkages instead of ether linkages and a rigid bi-aryl epoxy resin have been synthesized and compared with the commercially available diglycidyl ether of bis phenol F (BisF). A central hypothesis of this work is that flexibility or molecular mobility within a rigid network may impart enhanced distortional behavior of the epoxy amine network as measured by compression. The epoxy resins synthesized were bis[(glycidyloxy)phenyl)]-m-xylene (BGOPmX), bis[(glycidyloxy)phenyl)]-p-xylene (BGOPpX), and In this work, two tri-aryl and one bi-aryl epoxy resin, bis[(glycidyloxy)phenyl)]m-xylene (BGOPmX), bis[(glycidyloxy)phenyl)]-p-xylene (BGOPpX), and bis(glycidyloxy) biphenyl (BGOBP) are synthesized and cured with methylene dianiline and 4,4′-diamino diphenyl sulfone. Structure, property, and processing relationships are investigated and compared against diglycidyl ether of bis-phenol F epoxy resin to better understand the impact of rigid and flexible subunits within the network st...