Tripentaphenes are 2D nanocarbon lattices conceptually obtained from the assembly of acepentalene units. In this work, density functional theory is used to investigate their structural, electronic, and vibrational properties. Their bonding configuration is rationalized with a resonance mechanism, which is unique to each of the 2D assemblies. Their formation energies are found to lie within the range of other previously synthesized carbon nanostructures and phonon calculations indicate their dynamical stability. In addition, all studied tripentaphenes are metallic and display different features (e.g., Dirac cone) depending on the details of the atomic structure. The resonance structure also plays an important role in determining the electronic properties as it leads to delocalized electronic states, further highlighting the potential of the structures in nanoelectronics.