A　class　of　side-chain　type　ferrocene　macrocycles　with　a　radially　conjugated　system　is　introduced　in　this　study.　The　stereo　configurations　of　these　ferrocene　rings　were　determined　through　single-crystal　X-ray　diffraction　analysis.　Notably,　in　the　solid　state,　the　ferrocene　rings　exhibit　a　distinctive　herringbone　stacking　pattern　imposed　by　a　ferrocene-to-ring　host-guest　interaction.　Through　UV-vis　absorption　spectroscopy,　electrochemical　measurements,　and　theoretical　calculations,　valuable　insights　into　the　electronic　properties　of　these　rings　were　obtained.　In　addition,　the　single　crystal　of　macrocycle　A(2)B　demonstrates　a　second-order　nonlinear　optical　response.　As　a　class　of　organometallic　nanorings,　this　work　holds　great　potential　for　further　exploration　in　the　fields　of　organometallic　chemistry,　molecular　electronics,　and　host-guest　chemistry.