The　photoactive　macrocyclic　molecules　attract　attention　because　of　their　important　roles　in　supramolecular　chemistry　as　well　as　photoelectronic　applications.　Herein,　two　D-A　conjugated　macrocycles　containing　two　maleimide　nodes　have　been　successfully　obtained　via　an　one-pot　cascade　reaction　of　Perkin　and　imidization　condensations.　Owing　to　the　incorporation　of　two　bulky　1,4-dimethoxybenzene　moieties　at　the　narrow　maleimide　corners,　the　obtained　conjugated　macrocycles　have　been　equipped　with　two　adaptive　clamps,　which　can　adjust　to　the　guest　sizes　to　capture　the　guest　molecules.　Interestingly,　the　co-crystallization　with　larger-sized　polycyclic　aromatic　hydrocarbons　(PAHs)　leads　to　the　1:1　host-guest　complexes,　while　with　smaller-sized　solvents　results　in　the　1:2　complexes.　Furthermore,　the　rotatable　1,4-dimethoxybenzene　moieties　endowed　such　macrocyclic　fluorophores　with　pronounced　solvatochromic　and　aggregation-induced　emission　enhancement　(AIEE)　phenomena.　©　2024　Elsevier　Ltd