In this work, the electronic properties of singly anchored amino-p-terphenyl derivatives are characterized using automated chemical synthesis, single molecule electronics experiments, bulk scale electrochemistry, MD simulations, and NEGF-DFT calculations. Single molecule experiments reveal two well-defined conductance pathways in some amino-p-terphenyl derivatives due to a single electron oxidation event under an electric field. Bulk electrochemistry and spectroscopy experiments show that a radical cation state occurs when PPP is exposed to an electric field, which facilitates the formation of robust Au-C covalent linkages due to an oxidation event. Our results show that the formation of Au-C linkages is favored when the charge separated resonance state experiences minimal disruption. The introduction of substituents on the three benzene rings within the terphenyl system disrupts this state, hindering the high-conductance electron transport pathway. In addition, our work highlights the importance of non-covalent dimeric interactions in molecular electronics that can be leveraged for the design of materials for bulk scale measurements. MD simulations are used to understand the stacking conformations for various amino-p-terphenyl derivatives, and NEGF-DFT calculations are carried out to understand the electron transport behavior observed in single molecule experiments. Overall, our work highlights the formation of dynamic anchor groups in molecular junctions without requiring the cleavage or conversion of functional groups, which enhances the chemical toolbox available for constructing molecular electronics.