Multichromophoric　macrocycles　and　cyclophanes　are　important　supramolecular　architectures　for　the　elucidation　of　interchromophoric　interactions　originating　from　precise　spatial　organization.　Herein,　by　combining　an　axially　chiral　binaphthol　bisimide　(BBI)　and　a　bay-substituted　conformationally　labile　twisted　perylene　bisimide　(PBI)　within　a　cyclophane　of　well-defined　geometry,　we　report　a　chiral　PBI　hetero-cyclophane　(BBI-PBI)　that　shows　intramolecular　energy　and　solvent-regulated　chirality　transfer　from　the　BBI　to　the　PBI　subunit.　Excellent　spectral　overlap　and　spatial　arrangement　of　BBI　and　PBI　lead　to　efficient　excitation　energy　transfer　and　subsequent　PBI　emission　with　high　quantum　yield　(80–98　%)　in　various　solvents.　In　contrast,　chirality　transfer　is　strongly　dependent　on　the　respective　solvent　as　revealed　by　circular　dichroism　(CD)　spectroscopy.　The　combination　of　energy　and　chirality　transfer　affords　a　bright　red　circularly　polarized　luminescence　(CPL)　from　the　PBI　chromophore　by　excitation　of　BBI.　©　2022　The　Authors.　Angewandte　Chemie　International　Edition　published　by　Wiley-VCH　GmbH.