The　synthesis,　structure,　and　size-dependent　properties　of　ferrocene-embedded　conjugated　macrocycles　are　described.　The　one-pot,　two-component　＂shotgun＂　synthesis　greatly　expands　the　structural　diversity　and　functionality　of　nanohoops.　These　eta　5-type　coordination　metal-nanohoops　exhibit　intriguing　properties,　including　reversible　redox　behavior　and　collisional　quenching　with　fullerenes.　Notably,　the　addition　of　oxidants　enhances　their　fluorescence　intensity,　while　fullerenes　quench　it.　Detailed　theoretical　and　experimental　studies　reveal　that　fine-tuning　the　nanohoop　size　significantly　influences　not　only　the　molecular　conformation　but　also　its　electronic　structure　and　photophysical　properties.　Ferrocene-based　conjugated　macrocycles　were　efficiently　synthesized　by　a　＂shotgun＂　approach.　The　fluorescence　intensity　of　the　macrocycles　can　be　modulated　in　two　intriguing　ways:　enhancement　by　adding　an　oxidant　and　quenching　by　adding　fullerenes.