Thiophene‐Fused 1,4‐Thiaborins: Synthesis, Structures and Properties

ya-nan, Yan; Sun, Zhe; Li, Chenglong; Zhang, Jinyun; Liu, Xuguang; Liu, Xiujie

doi:10.1002/ajoc.201700063

Cited by 16 publications

(8 citation statements)

References 63 publications

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“…The following starting materials were synthesized according to literature materials: bis(2-bromophenyl)amine 55 and dimethyl mesitylboronate. 56 Air-sensitive reactions were performed under a nitrogen atmosphere using Schlenk techniques; no special precautions were taken to exclude air or moisture during workup and crystallization. HPLC analysis was conducted on a Shimadzu Prominence Modular HPLC system.…”

Section: Discussionmentioning

confidence: 99%

Azaborine as a Versatile Weak Donor for Thermally Activated Delayed Fluorescence

Sudhakar

Kuila

Stavrou

et al. 2023

ACS Appl. Mater. Interfaces

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Extensive research has been devoted to the development of thermally activated delayed fluorescence emitters, especially those showing pure-blue emission for use in lighting and full-color display applications. Toward that goal, herein we report a novel weak donor, 1,4azaborine (AZB), with complementary electronic and structural properties compared to the widely used dimethylacridan (DMAC) or carbazole (Cz) donors. Coupled with a triazine acceptor, AZB-Ph-TRZ is the direct structural analogue of the high-performance and well-studied green TADF emitter DMAC-TRZ and has ΔE ST = 0.39 eV, a photoluminescence quantum yield (Φ PL ) of 27%, and λ PL = 415 nm in 10 wt % doped mCP films. The shortened analogue AZB-TRZ possesses redshifted emission with a reduced singlet−triplet gap (ΔE ST = 0.01 eV) and fast reverse intersystem crossing (k RISC of 5 × 10 6 s −1 ) in mCP. Despite a moderate Φ PL of 34%, OLEDs with AZB-TRZ in mCP showed sky-blue emission with CIE 1931 (x,y) of (0.22,0.39) and a maximum external quantum efficiency (EQE max ) of 10.5%. Expanding the chemist's toolkit for the design of blue donor− acceptor TADF materials will enable yet further advances in the future, as AZB is paired with a wider range of acceptor groups.

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Section: Discussionmentioning

confidence: 99%

Azaborine as a Versatile Weak Donor for Thermally Activated Delayed Fluorescence

Sudhakar

Kuila

Stavrou

et al. 2023

ACS Appl. Mater. Interfaces

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“…The CÀ S bond lengths (1.72-1.74 Å) and CÀ SÀ C bond angles (101-103°) are comparable to the values found in the related DBTB structures. [78] The molecule of anti-anti-BBTB-OH is essentially Scheme 1. Molecular design of bis [1]benzothieno [1,4]thiaborins and their BODIPY complexes.…”

Section: Structural and Physicochemical Characterization Of Bbtb-ohmentioning

confidence: 99%

“…[72] Subsequently, seven-membered borepins fused with thiophene rings were introduced by Tavor and further studied by Ohshita, Adachi, and others. [73][74][75][76][77] Finally, Liu and co-workers reported successful synthesis of two isomeric dithieno [1,4]thiaborins (DTTBs, Scheme 1), [78] boron-based analogues of dithieno [1,4]thiazines.…”

Section: Introductionmentioning

confidence: 99%

Bis[1]benzothieno[1,4]thiaborins as a Platform for BODIPY Singlet Oxygen Photosensitizers

Marek

Urbanowicz

Wrochna

et al. 2023

Chemistry A European J

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A synthetic approach to two regioisomeric πelectron extended [1,4]thiaborins annulated with two benzothiophene units has been developed. The central thiaborin rings of the boracycles obtained exhibit different electronic properties; this is reflected in their different aromatic characters, boron Lewis acidity and UV-vis spectroscopic behavior. Thiaborins were converted to boron dipyrromethene (BODIPY) complexes. Their emission spectra exhibit two distinct bands resulting from 1 LE and 1 CT transitions. Strong near-infrared phosphorescence in Zeonex thin films at 77 K indicates efficient intersystem crossing and the formation of triplet states. Separation of HOMO and LUMO orbitals between boracyclic and BODIPY moieties facilitates electron transfer to a 1 CT state followed by a transition to the 3 LE triplet state located on the ligand. These unique properties of spiro thiaborin-BODIPY complexes were explored for their application as singlet-oxygen photosensitizers. They show excellent photocatalytic performance with singlet oxygen quantum yields reaching 77 % and full conversion of the model organic substrate achieved after 1.5 h with only 0.05 % mol catalyst load.

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“…An important recent finding in this regard was that the combination of furan rings with strongly electron-withdrawing groups substantially improves their resistance to oxidative degradation by lowering the compound’s highest occupied molecular orbital (HOMO) energy and therefore enhancing its overall stability. ,− The doping of conjugated π systems with trivalent boron atoms has emerged as an effective strategy to produce novel compounds with intriguing properties and functions. − …”

Section: Introductionmentioning

confidence: 99%

Boron-Doped α-Oligo- and Polyfurans: Highly Luminescent Hybrid Materials, Color-Tunable through the Doping Density

et al. 2021

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Doping of π-conjugated polymers or molecular compounds with trivalent boron atoms has recently emerged as a viable strategy to produce new materials with intriguing properties and functions. The combination of boron with furan moieties has been only scarcely explored so far, although the resulting furan-based materials have several notable features, including favorable optoelectronic properties and improved sustainability. Herein, we investigate the doping of α-polyfurans with a varying number of boron atoms. A series of poly(oligofuran boranes) and oligofuran-bridged bisboranes have been prepared via microwave-assisted Stille-type catalytic cross-coupling protocols. In the solid-state structures of the molecular compounds, the furan and the borane moieties exhibit a strictly coplanar arrangement; the derivative with a pentafuran bridge forms a dimeric structure in the solid state. All new compounds show considerable absorption and emission features in the visible range that arise from π–π* transitions in the oligofurylborane backbone. They are highly luminescent with quantum yields between 89 and 97% for the bisboranes and up to 87% for the difuran-bridged polymer PB2F. Their emission colors can be effectively tuned in the visible range from blue to orange via the length of the oligofuran linker. Spectroelectrochemical investigations on the difuran-bridged bisborane BB2F and polymer PB2F revealed fully reversible stepwise reductions to the respective radical anion (polaron), with absorption features in the near-infrared (NIR) region, and subsequently to a dianion (dipolaron). Overall, the doping of α-oligofurans with boron leads to a decrease of the frontier orbital energies, a reduction of the electronic band gap, and the formation of very robust and oxidatively stable materials.

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Thiophene‐Fused 1,4‐Thiaborins: Synthesis, Structures and Properties

Cited by 16 publications

References 63 publications

Azaborine as a Versatile Weak Donor for Thermally Activated Delayed Fluorescence

Azaborine as a Versatile Weak Donor for Thermally Activated Delayed Fluorescence

Bis[1]benzothieno[1,4]thiaborins as a Platform for BODIPY Singlet Oxygen Photosensitizers

Boron-Doped α-Oligo- and Polyfurans: Highly Luminescent Hybrid Materials, Color-Tunable through the Doping Density

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