A dyad, 1, built on an artificial special pair (bis(meso-nonyl)zinc(II)porphyrin), [Zn 2 ], a spacer (biphenylene), a bridge (1,4-benzene), and an antenna (di-meso-(3,5-di(t-butyl)phenyl)porphyrin free base), FB, is prepared by Suzuki coupling and is analyzed by absorption and steady state, and time-resolved emission spectroscopy at 298 and 77 K. Using bases from the Förster theory, evidence for two pathways for S 1 energy transfer, FB* → [Zn 2 ], and [Zn 2 ]* → FB, along with their respective rates, k ET (S 1 ) 1 and k ET (S 1 ) -1 , are extracted from the comparison of the fluorescence decays monitored at the emission maximum. At 77 K, the unquenched (1.79 ([Zn 2 ]) and 10.6 ns (FB)) and quenched components (<100 ps; i.e. k ET (S 1 ) > 10 (ns) -1 ), are observed, hence, demonstrating the bidirectional paths with no back energy transfer. A 298 K, only two components are detected (0.44 ([Zn 2 ]) and 2.64 ns (FB)) and the resulting reduced t F s indicates back energy transfer, therefore cycling and equilibrium. Their global rates are 0.31 and 1.8 (ns) -1 for k ET (S 1 ) 1 and k ET (S 1 ) -1 at 298 K. This large temperature dependence on k ET (S 1 ) is fully consistent with the participation of thermal activation. Finally, DFT calculations (B3LYP) were used to illustrate a clear correlation between the relative k ET (S 1 )s and the amplitude of the MO couplings between the artificial special pair and the antenna.