Near-Infrared Twisted Polycyclic Arene-Fused BisBODIPYs through a Tandem Inter- and Intramolecular Scholl Reaction

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 25, 2025

Five novel polyaromatic-ring-fused bisBODIPYs have been synthesized from corresponding readily available α-arylBODIPYs through a FeCl3-mediated tandem inter- and intramolecular oxidative aromatic coupling reaction. These resultant show twisted planar conformations, strong absorptions (ε up to 1.8 × 105 M-1 cm-1), good fluorescence emissions in the near-infrared region (NIR, 660-734 nm) intersystem crossing efficiencies (ΦΔ = 18.9% for dimer 2d toluene), demonstrating their promising potential applications as heavy-atom-free photosensitizers.

Язык: Английский

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Dibenzothieno and dibenzothieno[2,3-d]thieno [a]-fused BODIPYs: synthesis, unique structure and photophysical properties

Materials Chemistry Frontiers, Год журнала: 2024, Номер 8(20), С. 3266 - 3271

Опубликована: Янв. 1, 2024

A simple synthetic approach to aromatic heterocyclic [ a ]-fused BODIPYs, which exhibit “butterfly-shaped” crystal structures, high Φ F , and tunable HOMO levels.

Язык: Английский

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B←N Lewis Pair-Functionalized Perylenes: Tuning Optoelectronic Properties via Regioisomerization

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 14, 2025

Herein, we report two peri-regioisomers of B←N Lewis pair-functionalized perylenes: the centrosymmetric PBNPf1 and mirror-symmetric PBNPf2. Mirror-symmetric functionalization more effectively tunes photoelectronic properties. The LUMO energy levels PBNPf2 are stabilized to -3.00 eV -3.30 eV. Additionally, emission maxima shifted 574 628 nm, with fluorescence quantum yields up 96% 87%, respectively.

Язык: Английский

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Asymmetric and Symmetric S-zig-zag-Fused BODIPYs: Synthesis and Photophysical and Oxidative Properties

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 18, 2025

We present a new, straightforward, and versatile approach that utilizes regioselective brominated precursors to synthesize both asymmetric symmetric S-zig-zag-fused BODIPYs (s-TFB bis-TFB) in moderate yields (45% 40%, respectively). X-ray structure analyses reveal the planar rigidity of BODIPY skeleton is progressively enhanced with an increasing number thiopyran rings. The annulation S-heteroaromatic rings at zig-zag edge core results blue-shifted absorption emission spectra, bis-TFB exhibiting maxima 530 539 nm elevated LUMO energy levels. In contrast, oxidation s-TFB m-CPBA demonstrates significant site selectivity, affording four products, namely s-s-SFB, s-bis-SFB, bis-s-SFB, bis-bis-SFB, ranging from 22% 36%. These oxidated derivatives display large red-shifted spectra (e.g., 648 735 for s-bis-SFB), along more stable HOMO levels reduced HOMO-LUMO gaps. This cyclization/oxidation strategy enables precise tuning optoelectronic properties, opening new avenues dye design application.

Язык: Английский

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Oxa-phenalene [b]-fused BODIPY Dyes: Synthesis, Structures, and Photophysical Properties

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134728 - 134728

Опубликована: Май 1, 2025

Язык: Английский

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Diarenofuran[b]-fused BODIPYs: One-Pot S_NAr-Suzuki Synthesis and Properties

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 15, 2024

We present a streamlined methodology that integrates regioselective tetrahalogen-BODIPY and

Язык: Английский

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N-Bridged BODIPY Dimers: Exploring the Electron-Rich and Electron-Poor Coupling Limit via Pyrrole and Pyridine Annulation

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 17, 2024

A facile access to N-heteroaryl-fused bis-BODIPY scaffolds has been developed. BODIPY dimer with an α,α-amine linker serves as a starting material obtain pyrrole- and pyridine-fused BODIPYs, either by direct oxidation or oxidative condensation aldehyde building block. Both species mark antipodal conjugative coupling conditions that result in distinct spectral outcomes. In stark contrast the pyrrole fusion, pyridine-coupled show unique panchromatic absorption profiles.

Язык: Английский

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Adjustable Regioselectivity for the Diels–Alder Reactions of Sulfolenodipyrrins upon Molecular Engineering on H-Bonds

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(21), С. 15678 - 15685

Опубликована: Окт. 15, 2024

The Diels–Alder reactions of sulfolenodipyrrins prove to be an efficient way construct aromatic ring-fused dipyrrins. However, adjustable annulation is still hard achieve. To address this, molecular engineering on the H-bond has been employed. α-position aryl group-modified have synthesized react with various dienophiles in reactions, affording monoannulation products different regioselectivity good yields (45–76%). remaining sulfolenopyrrole monoadducts can undergo further fusion presence and TEMPO, giving bisadducts a lactam subunit appropriate yield. According crystal structures theoretical calculations, intramolecular H-bonds between α-substituent nearby pyrrole confine conjugation pathway dipyrrin core. With respect normal NH-sulfolenopyrrole, imino-type one features low aromaticity, from which SO2 extrusion generates more stable dipyrrin-diene, achieving regioselectivity. In addition, ring results red-shifted absorption emission spectra, units regulate intensity. This work shows versatility regulating reaction through confinement system.

Язык: Английский

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Multicomponent Diversity-Oriented Access to Boronic-Acid-Derived Pyrrolide Salicyl-Hydrazone Fluorophores with Strong Solid-State Emission

Inorganic Chemistry, Год журнала: 2024, Номер 63(45), С. 21397 - 21409

Опубликована: Окт. 31, 2024

Fluorescent molecular platforms are highly sought after for their applications in biology and optoelectronics but face challenges with solid-state emission quenching. To address this, bulky substituents or aggregation-induced luminogens to restrict intramolecular motion used enhance the brightness. Here, we have successfully engineered a novel class of boron complexed pyrrolide salicyl-hydrazone fluorophores named BPSHY. These dyes were synthesized through diversity-oriented condensation pyrrole salicylaldehyde derivatives combined various aromatic boronic acids. The resulting 3D structures, owing axially substituted aryl groups, impart excellent solubility variety solvents. Significantly, BPSHY exhibit strong absorption visible region remarkably large Stokes shifts. Crucially, they demonstrate intense aqueous solutions due effects. In solid-states, these achieve high quantum yields, reaching up 58%. Further expanding utility, developed two new probes: one incorporating morpholine another containing triphenylphosphine salt. Both them found specifically label subcellular organelles such as lysosomes mitochondria within live cells. Notably, probes exceptional staining efficacy two-photon fluorescence feature. This highlights considerable promise monitoring visualizing dynamic transformations organelles.

Язык: Английский

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Emission‐Tunable B←N Lewis Pair‐Functionalized Naphthalenes

Chemistry - A European Journal, Год журнала: 2024, Номер 31(8)

Опубликована: Дек. 4, 2024

Abstract Herein, we simultaneously synthesized three different double B←N Lewis pair‐functionalized naphthalenes including the asymmetric BNNY and BNNO mirror‐symmetric BNNR , via a one‐pot method. The annulation modes of pairs substituents on boron atoms efficiently tune molecular frontier orbitals emission colors. α‐Position fusion leads to significant enhancement HOMO energy level decrease in HOMO‐LUMO gap, while electron‐withdrawing groups attached atom make LUMO more stable. In particular, is as low −3.12 eV. emit cyan, green, red fluorescence at 509, 534, 620 nm, respectively, with quantum yields 24 %, 49 30 respectively.

Язык: Английский

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