Summary: | Tetraamino-tetranitro-azacalixarene <b>5</b> is at the crossroad of two different families of compounds depending on the conditions and the agent used to reduce the NO<sub>2</sub> groups: (1) azacalixphyrin <b>7</b> in neutral medium, or (2) phenazinium of type <b>8</b> in acidic medium. The key role of the N-substituted amino functions at the periphery is highlighted by investigating octaaminoazacalixarene as a model compound, and by using the corresponding tetrahydroxy-tetranitro-azacalixarene <b>15</b> as a precursor, which behaves differently.
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