To　expand　the　properties　of　epoxy　coatings　for　emerging　technologies,　herein,　a　pillar[5]arene-based　epoxy　compound　(PAEP)　containing　unique　pillar-shaped　three　dimensional　macrocyclic　structure　was　prepared　and　cured　with　conventional　4,4′-diaminodiphenylmethane　(DDM).　Interestingly,　the　PAEP　exhibited　a　strong　host-guest　complexation　with　1,4-dibromobutane　(DBrBu),　a　potential　organic　antibacterial　agent,　with　a　complex　constant　of　215.7　±　11.02　M−1.　Furthermore,　the　PAEP/DDM　resin　possessed　enhanced　mechanical　and　thermal　properties,　probably　due　to　the　increase　of　chain-entanglement　brought　about　by　the　cyclic　structure.　Also,　the　PAEP/DDM　resin　exhibited　excellent　intrinsic　flame　retardant　properties,　including　significantly　reduced　peak　heat　release　rate　(153.5　W·g−1)　and　high　limit　oxygen　index　(LOI)　(34.7%),　and　a　V-0　rating　in　the　UL-94　test.　Moreover,　the　PAEP/DDM　resin　exhibited　a　remarkably　low　dielectric　constant　of　2.25　at　106　Hz　for　telecommunication　applications,　which　is　much　lower　than　the　current　epoxy　resins　with　nanoporous　inorganic　modifiers.　Therefore,　the　incorporation　of　pillar[5]arene　is　a　fruitful　pathway　to　expand　the　properties　of　epoxy　resins　and　provides　a　new　platform　for　decoration　for　various　applications.　©　2022　Elsevier　B.V.