In this work, we investigate the electron transport behavior of singly anchored p-terphenyl derivatives using a combination of automated chemical synthesis, single molecule electronics experiments, molecular dynamics (MD) simulations, and non-equilibrium Green's function-density functional theory (NEGF-DFT) calculations. Synthesis of pterphenyl derivatives was performed using a rapid Suzuki-Miyaura cross coupling (SMCC) method with reduced reaction time and temperature . Following synthesis, the electronic properties of these molecules were characterized using the scanning tunneling microscope-break junction (STM-BJ) technique . Our results show that 4-amino-pterphenyl (PPP) has a surprisingly well-defined high conductance feature despite the presence of only one terminal anchor, but this high conductance feature is greatly diminished or absent in all other terphenyl derivatives studied in this work. Our results further reveal a low conductance feature for all singly anchored amino-p-terphenyl derivatives studied in this work, which arises due to non-covalent intermolecular interactions. Flicker noise analysis and machine learning methods such as correlation 2D analysis and Gaussian mixture modeling (GMM) are used to understand the conductance behavior. In addition, cyclic voltammetry (CV), bulk-scale electrolysis, and electron spin resonance (ESR) were used to understand the origin of the high conductance state, which arises due to Au-C bond formation due to a single electron oxidation event for molecular junctions .