A new type of –NH– bridged azacalix[2]arene[2]carbazoles has been synthesized by aromatic nucleophilic substitution reaction via one pot and/or fragment coupling strategy. Both symmetric and unsymmetric macrocycles are obtained. X-ray single crystal analysis reveals 1,3-alternation conformation of the macrocycle. The spectroscopic and electrochemical properties of the macrocycles are also explored.