Abstract
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.
Highlights
Two-photon absorption (TPA) is a non-linear optical property that depends on the third-order optical susceptibility (χ3) and it scales with the square of the light intensity used in the excitation process (He et al, 2008)
Many different types of organic chromophores have been explored in an attempt to improve the TPA properties, from simple organic molecules (SOMs), to polymers, nanoparticles and composites tailored for diverse applications (Zou et al, 2011; Marcelo et al, 2015; Mariz et al, 2015; Santos et al, 2018)
Despite its simple structure, it can compete in terms of quantum yields, glum and even TPA cross sections with previously described TPA and CPL (TPCPL) emitters requiring a more demanding synthetic approach
Summary
Organic materials presenting circularly polarized luminescence (CPL) (Riehl and Richardson, 1977; Kumar et al, 2015; Sanchez-Carnerero et al, 2015; Longhi et al, 2016; Tanaka et al, 2018) have recently emerged as promising candidates for advanced optical applications (Zinna et al, 2015; Han et al, 2018; Shi et al, 2018; Zheng et al, 2018; Burrezo et al, 2019; David et al, 2019; Jiménez et al, 2019; Pop et al, 2019; Yang and Zhong, 2019). Many opportunities exist for the development of new and simple architectures combining reasonable glum values and TPA cross sections (σ2) together with good quantum yields ( F) Among such possibilities simple organic molecules (SOMs) are appreciated owing to their high solubility and processability (Kumar et al, 2015; Sanchez-Carnerero et al, 2015; Longhi et al, 2016; Tanaka et al, 2018). Despite its simple structure, it can compete in terms of quantum yields, glum and even TPA cross sections with previously described TPCPL emitters requiring a more demanding synthetic approach
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