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Doubly boron-doped thermally activated delayed fluorescence (TADF) emitters based on a 9,10-diboraanthracene (DBA) acceptor decorated with ortho-donor groups (Cz2oDBA, 2; BuCz2oDBA, 3; DMAC2oDBA, 4) are prepared to realize high-efficiency green-to-red organic light-emitting diodes (OLEDs). X-ray diffraction analyses of 2 and 4 reveal the symmetrical and highly twisted ortho-donor-acceptor-donor (D-A-D) structure of the emitters. The twisted conformation leads to a very small energy splitting (ΔE <0.08 eV) between the excited singlet and triplet states that gives rise to strong TADF, as supported by theoretical studies. Depending on the strength of the donor moieties, the emission color is fine-tuned in the visible region from green (2) to yellow (3) to red (4). Carbazole-containing 2 and 3 exhibit high photoluminescence quantum yields (PLQYs) approaching 100 %, whereas DMAC-substituted 4 is moderately emissive (PLQY=44 %) in a doped host film. Highly efficient green-to-red TADF-OLEDs are realized with the proposed ortho-D-A-D compounds as emitters. The green and yellow OLEDs incorporating Cz2oDBA (2) and BuCz2oDBA (3) emitters exhibit high external quantum efficiencies (EQEs) of 26.6 % and 21.6 %, respectively. In particular, the green device shows an excellent power efficiency above 100 lm W . A red OLED fabricated with a DMAC2oDBA (4) emitter exhibits a maximum EQE of 10.1 % with an electroluminescence peak at 615 nm.
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http://dx.doi.org/10.1002/chem.202002968 | DOI Listing |
Dalton Trans
February 2025
Laboratory for Chemical Computation and Modeling, Institute for Computational Science and Artificial Intelligence, Van Lang University, Ho Chi Minh City, Vietnam.
A theoretical investigation, employing density functional theory with the PBE functional and the Def2-TZVP basis set, comprehensively explores the geometric and electronic structures and properties of the boron doped scandium clusters BSc with = 2-3 and = 3-13. Introduction of B atoms significantly enhances the stability of the resulting clusters with respect to the initial counterparts. As the number of B atoms increases, the stability of the doped clusters improves, following the order: BSc > BSc > BSc > Sc.
View Article and Find Full Text PDFChem Sci
May 2023
Institut für Anorganische und Analytische Chemie, Goethe-Universität Frankfurt Max-von-Laue-Straße 7 D-60438 Frankfurt am Main Germany
9,10-Diboratatriptycene salts M[RB(μ-CH)BR] (R = H, Me; M = Li, K, [-BuN]) have been synthesized [4 + 2] cycloaddition between doubly reduced 9,10-dihydro-9,10-diboraanthracenes M[DBA] and benzyne, generated from CHF and CHLi or LiN(-Pr). [HB(μ-CH)BH] reacts with CHCl to form quantitatively the bridgehead-derivatized [ClB(μ-CH)BCl], while twofold H abstraction with B(CF) in the presence of SMe leads cleanly to the diadduct (MeS)B(μ-CH)B(SMe). Photoisomerization of K[HB(μ-CH)BH] (THF, medium-pressure Hg lamp) provides facile access to diborabenzo[]fluoranthenes, a little explored form of boron-doped polycyclic aromatic hydrocarbons.
View Article and Find Full Text PDFJ Phys Chem A
November 2022
Schulich Department of Chemistry, Technion, Haifa 3200003, Israel.
Qualitative aromaticity-based arguments are often used to explain singlet fission (SF) properties in polycyclic conjugated systems. It has been shown by Fowler and collaborators that magnetically induced ring currents are associated with transitions between occupied and unoccupied molecular orbitals (MOs). Since SF has to do with relative energies of electronic states, it was hypothesized that induced currents may indicate SF properties.
View Article and Find Full Text PDFChemistry
September 2022
Institute for Inorganic Chemistry, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
The reaction of a cyclic alkyl(amino)carbene (CAAC)-stabilized thiazaborolo[5,4-d]thiazaborole (TzbTzb) with strong Brønsted acids, such as HCl, HOTf (Tf=O SCF ) and [H(OEt ) ][BAr ] (Ar =3,5-(CF ) C H ), results in the protonation of both TzbTzb nitrogen atoms. In each case X-ray crystallographic data show coordination of the counteranions (Cl , OTf , BAr ) or solvent molecules (OEt ) to the doubly protonated fused heterocycle via hydrogen-bonding interactions, the strength of which strongly influences the H NMR shift of the NH protons, enabling tuning of both the visible (yellow to red) and fluorescence (green to red) colors of these salts. DFT calculations reveal that the hydrogen bonding of the counteranion or solvent to the protonated nitrogen centers affects the intramolecular TzbTzb-to-CAAC charge transfer character involved in the S →S transition, ultimately enabling fine-tuning of their absorption and emission spectral features.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
February 2022
Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
Herein we devise and execute a new synthesis of a pristine boron-doped nanographene. Our target boron-doped nanographene was designed based on DFT calculations to possess a low LUMO energy level and a narrow band gap derived from its precise geometry and B-doping arrangement. Our synthesis of this target, a doubly B-doped hexabenzopentacene (B -HBP), employs six net C-H borylations of an alkene, comprising consecutive hydroboration/electrophilic borylation/dehydrogenation and BBr /AlCl /2,6-dichloropyridine-mediated C-H borylation steps.
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