Recognition Behavior of a Porphyrin Heterodimer Self‐Assembled through an Amidinium‐Carboxylate Salt Bridge

Abstract

In this study, we synthesized two porphyrins (P1 and P2) featuring two carboxybenzene and two 2‐aminoquinoline units at meso‐positions, respectively, and these porphyrins quantitatively self‐assembled into a heterodimer (P1⋅P2) through an amidinium‐carboxylate salt bridge formation in aprotic and non‐polar solvents. The capsule‐like dimer, possessing two cofacial porphyrin units, binds electron‐deficient aromatic compounds as guests, forming three‐layer π‐aromatic structures, and NMR and UV/Vis spectroscopies were used to determine the association constants (e. g., 1,3,5‐trinitrobenzene: Ka>104 M−1 in dichloromethane). The association constants and the rates of association and dissociation between the dimer and the guests were related to the electron deficiency of the aromatic guests.

Discovery of benzoheterocyclic-substituted amide derivatives as apoptosis signal-regulating kinase 1 (ASK1) inhibitors

“…Intermediate 29 was synthesized through a Heck Reaction using starting materials 27 and 28 . 29 The remaining synthetic procedures were similar to those described in Scheme 3.…”