Simple Perylene Diimide Cyclohexane Derivative With Combined CPL and TPA Properties Reiné Díaz, Pablo Ortuño Guzmán, Ana María Mariz, Inês F. A. Ribagorda, María Cuerva Carvajal, Juan Manuel González Campaña, Araceli Maçôas, Ermelinda Miguel Álvarez, Delia Perylene diimide (PDI) Electronic circular dichroism (ECD) Circularly polarized luminiscence (CPL) Two-photon absorption Non-linear emission The Supplementary Material for this article can be found online at: https://www.frontiersin.org/articles/10.3389/fchem. 2020.00306/full#supplementary-material In this work we describe the linear and non-linear (chiro)optical properties of an enantiopure bis-perylenediimide (PDI) cyclohexane derivative. This compound exhibits upconversion based on a two-photon absorption (TPA) process with a cross-section value of 70 GM together with emission of circularly polarized luminescence (CPL), showing a glum in the range of 10−3. This simple structure represents one of the scarce examples of purely organic compounds combining both TPA and CPL responses, together with large values of molar absorptivity and fluorescence quantum yield with emission in the 500–600 nm. Self-assembly induced by introduction of a poor solvent allows for a spectacular shift of the emission into the near-infrared (NIR, 650–750 nm) by formation of well-defined rotationally displaced dimers. Therefore, we are here presenting a versatile platform whose optical properties can be simply tuned by self-assembly or by functionalization of the electron-deficient aromatic core of PDIs. 2020-06-02T12:12:05Z 2020-06-02T12:12:05Z 2020-04-21 info:eu-repo/semantics/article Reine P, Ortuño AM, Mariz IFA, Ribagorda M, Cuerva JM, Campaña AG, Maçôas E and Miguel D (2020) Simple Perylene Diimide Cyclohexane Derivative With Combined CPL and TPA Properties. Front. Chem. 8:306. [doi: 10.3389/fchem.2020.00306] http://hdl.handle.net/10481/62335 10.3389/fchem.2020.00306 eng http://creativecommons.org/licenses/by/3.0/es/ info:eu-repo/semantics/openAccess Atribución 3.0 España Frontiers Media