Aggregation-induced　emission　enhancement　and　aggregation-induced　chirality　inversion　are　two　individual　phenomena　for　the　enantiomerically　pure　organic　dyes　in　the　aggregates.　Herein　we　reported　for　the　first　time　that　these　two　interesting　phenomena　could　be　observed　simultaneously　in　the　aggregated　states　of　enantiomerically　pure　S/R-1,1＇-binaphthol　annulated　perylene　diimides,　in　which　two　perylene　diimides　moieties　were　bridged　by　S/R-1,1＇-binaphthol　(BINOL)　at　the　bay　positions.　Owing　to　the　rotatable　C2　axes　between　two　naphthol　annulated　perylene　diimides　moieties,　both　of　them　display　intrinsic　behaviors　of　aggregation-induced　emission　enhancements.　At　the　same　time,　due　to　the　steric　hindrances　in　the　imide　and　methoxy　positions,　the　neighboring　two　pi-systems　of　these　two　unique　polycyclic　aromatic　imides　in　poor　solvents　are　preferable　to　adopt　a　cross-stacking　mode　and　thus　form　helical　Xaggregates　of　opposite　chirality　(M/P)　with　chirality　inversion　characteristics　in　their　circular　dichroism　and　circularly　polarized　luminescence　spectroscopic　studies.　(C)　2021　Published　by　Elsevier　B.V.　on　behalf　of　Chinese　Chemical　Society　and　Institute　of　Materia　Medica,　Chinese　Academy　of　Medical　Sciences.