2023
DOI: 10.1021/acs.orglett.3c02858
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Red-Shifted Emission in Multiple Resonance Thermally Activated Delayed Fluorescent Materials through Malononitrile Incorporation

Athan T. Gogoulis,
Ryoga Hojo,
Katrina Bergmann
et al.

Abstract: Multiple resonance thermally activated delayed fluorescent (MR-TADF) materials offer higher color purity than conventional TADF materials but suffer from aggregation-caused quenching (ACQ) and rarely exhibit red emission. Herein, two malononitrile-substituted emitters are synthesized from a quinolino­[3,2,1-de]­acridine-5,9-dione (QAO) MR-TADF precursor. Both materials maintain MR-TADF, while they display red-shifted fluorescence. They also overcome ACQ, displaying enhanced emission upon aggregation in solutio… Show more

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Cited by 6 publications
(2 citation statements)
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“…Meanwhile, the electrochemical characterization of (Cz−BTZ−Py) 2 Pt(OTf) 2 was conducted by cyclic voltammetry (CV) (Figure S9) in DMF. And the electrochemical energy gap Egec ${{E}_{g}^{ec}}$ for (Cz−BTZ−Py) 2 Pt(OTf) 2 were calculated to be 1.65 eV, [38,39] which had good agreement with their optical energy gap. In the fluorescence emission spectra (Figure 2b), the supramolecular dimer (Cz−BTZ−Py) 2 Pt(OTf) 2 showed good emission in the NIR region, indicating the supramolecular dimer held great potential for use in NIR imaging.…”
Section: Resultsmentioning
confidence: 81%
“…Meanwhile, the electrochemical characterization of (Cz−BTZ−Py) 2 Pt(OTf) 2 was conducted by cyclic voltammetry (CV) (Figure S9) in DMF. And the electrochemical energy gap Egec ${{E}_{g}^{ec}}$ for (Cz−BTZ−Py) 2 Pt(OTf) 2 were calculated to be 1.65 eV, [38,39] which had good agreement with their optical energy gap. In the fluorescence emission spectra (Figure 2b), the supramolecular dimer (Cz−BTZ−Py) 2 Pt(OTf) 2 showed good emission in the NIR region, indicating the supramolecular dimer held great potential for use in NIR imaging.…”
Section: Resultsmentioning
confidence: 81%
“…12–15 However, examples of orange/red MR-TADF OLEDs remain relatively rare due to the challenges in emitter design to red-shift the emission of the emitters. 6 There are currently two primary methods for shifting the emission to the red: (1) Enhancing the donor and acceptor strength by constructing systems with electron-accepting (A) and donating atoms (D) in A- para -A and D- para -D regiochemistry; 16–19 (2) Decorating the MR-TADF core with donor or acceptor substituents to tune the energy of the emissive core; 20,21 note that the use of too strong donors or acceptors results in the excited state being of long-range charge transfer (LRCT) character, resulting in less bright and broader emission. Dimerization of MR-TADF emitters is a distinct strategy for realizing red-shifted emission via extending the conjugation area.…”
Section: Introductionmentioning
confidence: 99%