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Efficient Narrowband Circularly Polarized Light Emitters Based on 1,4‐B,N‐embedded Rigid Donor–Acceptor Helicenes

Fangyuan Zhang, Florian Rauch, Asim Kumar Swain, Todd B. Marder, Prince Ravat

2023Angewandte Chemie International Edition104 citationsDOIOpen Access PDF

Abstract

Abstract Narrow‐band emission is essential for applicable circularly polarized luminescence (CPL) active materials in ultrahigh‐definition CP‐OLEDs. One of the most promising classes of CPL active molecules, helicenes, however, typically exhibit broad emission with a large Stokes shift. We present, herein, a design strategy capitalizing on intramolecular donor‐acceptor interactions between nitrogen and boron atoms to address this issue. 1,4‐B,N‐embedded configurationally stable single‐ and double helicenes were synthesized straightforwardly. Both helicenes show unprecedentedly narrow fluorescence and CPL bands (full width at half maximum between 17–28 nm, 0.07–0.13 eV) along with high fluorescence quantum yields (72–85 %). Quantum chemical calculations revealed that the relative localization of the natural transition orbitals, mainly on the rigid core of the molecule, and small values of root‐mean‐square displacements between S 0 and S 1 state geometries, contribute to the narrower emission.

Topics & Concepts

Intramolecular forceFluorescenceAtomic orbitalMoleculeAcceptorStokes shiftLuminescenceChemistryChromophorePhotochemistryMaterials scienceMolecular physicsOptoelectronicsPhysicsStereochemistryOpticsElectronCondensed matter physicsQuantum mechanicsOrganic chemistrySynthesis and Properties of Aromatic CompoundsLuminescence and Fluorescent MaterialsOrganic Electronics and Photovoltaics