Dataset Information

Brominated B₁-Polycyclic Aromatic Hydrocarbons for the Synthesis of Deep-Red to Near-Infrared Delayed Fluorescence Emitters.

ABSTRACT: Bromo-functionalized B₁-polycyclic aromatic hydrocarbons (PAHs) with LUMOs of less than -3.0 eV were synthesized and used in cross-couplings to form donor-acceptor materials. These materials spanned a range of S₁ energies, with a number showing thermally activated delayed fluorescence and significant emission in the near-infrared region of the spectrum. These B₁-PAHs represent a useful family of acceptors that can be readily synthesized and functionalized.

SUBMITTER: Yuan K

PROVIDER: S-EPMC10425980 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature

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Publications

Brominated B1-Polycyclic Aromatic Hydrocarbons for the Synthesis of Deep-Red to Near-Infrared Delayed Fluorescence Emitters.

Yuan Kang K Gupta Abhishek Kumar AK Si Changfeng C Uzelac Marina M Zysman-Colman Eli E Ingleson Michael James MJ

Organic letters 20230727 31

Bromo-functionalized B1-polycyclic aromatic hydrocarbons (PAHs) with LUMOs of less than -3.0 eV were synthesized and used in cross-couplings to form donor-acceptor materials. These materials spanned a range of S1 energies, with a number showing thermally activated delayed fluorescence and significant emission in the near-infrared region of the spectrum. These B1-PAHs represent a useful family of acceptors that can be readily synthesized and functionalized. ...[more]

PMID: 37498083

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Project description:Nitrogen substitutions have shown a great impact for the development of thermally activated delayed fluorescence (TADF)-based organic light-emitting diode (OLED) materials. In particular, much focus has been devoted to nitrogen-substituted polycyclic aromatic hydrocarbons (PAHs) for TADF emitters. In this context, we provide here a molecular design approach for symmetric nitrogen substitutions in fused benzene ring PAHs based on the dibenzo[a,c]picene (DBP) molecule. We designed possible donor-acceptor (D-A) compounds with dimethylcarbazole (DMCz) and dimethyldiphenylamine (DMDPA) donors and studied the structure and photophysics of the designed D-A compounds. The twisted and extended D-A-type PAH emitters demonstrate red and near-infrared (NIR) TADF emission. Nitrogen substitutions lead to significant LUMO stabilization and reduced HOMO-LUMO energy gaps as well. Additionally, we computed significantly smaller singlet-triplet energy splittings (ΔEST) in comparison to non-nitrogen-substituted compounds. The investigated ortho-linked D-A compounds show relatively large donor-acceptor twisting separation and small ΔEST compared to their para-linked counterparts. For higher number nitrogen (4N)-substituted emitters, we predict small adiabatic ΔEST (ΔESTadia) in the range 0.01-0.13 eV, and with the tert-butylated donors, we even obtained ΔESTadia values as small as 0.007 eV. Computed spin-orbit coupling (SOC) for the T1 triplet state on the order of 0.12-2.28 cm-1 suggests significant repopulation of singlet charge transfer (1CT) excitons from the triplet CT and locally excited (3CT+LE) states. Importantly, the small ΔESTadia and large SOC values induce a reverse intersystem crossing (RISC) rate as high as 1 × 106 s-1, which will cause red and NIR delayed fluorescence in the 4N-substituted D-A emitters. Notably, we predict red TADF emission for the para-linked compound B4 at 670 nm and the ortho-linked compound D4 at 713 nm and delayed NIR emission at 987 and 1217 nm for the ortho-linked compounds D3 and E3, respectively.

Dataset Information

Brominated B₁-Polycyclic Aromatic Hydrocarbons for the Synthesis of Deep-Red to Near-Infrared Delayed Fluorescence Emitters.

Publications

Brominated B<sub>1</sub>-Polycyclic Aromatic Hydrocarbons for the Synthesis of Deep-Red to Near-Infrared Delayed Fluorescence Emitters.

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