Two　o-carborane-based　π-conjugated　macrocycles　were　synthesized　via　the　oxidative　coupling　of　acetylene-terminated　o-carborane　precursors.　Single-crystal　X-ray　diffraction　analysis　unambiguously　revealed　their　unique　porous　supramolecular　structures,　which　exhibit　micropore　characteristics.　These　novel　macrocycles　exhibit　aggregation-induced　emission　in　both　the　aggregated　state　and　the　solid　state.　This　work　provides　a　new　design　strategy　for　developing　o-carborane　macrocyclic　molecules　with　excellent　photophysical　properties.　Based　on　the　obvious　fluorescence　quenching　phenomenon　of　macrocycles　by　1,4-dinitrobenzene　and　2,4,6-trinitrophenol,　it　can　be　concluded　that　these　macrocyclic　compounds　have　promising　potential　as　sensors　for　nitroaromatics.　©　2023　The　Royal　Society　of　Chemistry.