Simple Perylene Diimide Cyclohexane Derivative With Combined CPL and TPA Properties
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AuthorReiné 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 absorptionNon-linear emission
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]
SponsorshipMinisterio de Ciencia, Innovacion y Universidades PG2018-101181-B-I00; Spanish Government CTQ2017-85454-C2-1-P; European Research Council (ERC) ERC-2015-STG-677023; MINECO RyC-2013-12943; Spanish Government; Portuguese Foundation for Science and Technology; POCI; European Union (EU) PTDC/NAN-MAT/29317/2017 PTDC/QUI-QFI/29319/2017 UIDB/00100/2020
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.