Introducing of an Unexplored Aza-BODIPY Diradicaloids with 4-(2,6-Ditert-butyl)phenoxyl Radicals Located in 1,7-Positions of the Aza-BODIPY Core DOI

Morris Oyelowo,

Jacob W. Schaffner,

Towhidi Illius Jeaydi

et al.

Inorganic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 27, 2024

We have prepared and characterized two diradicaloid systems 5a 5b that originated from the oxidation of a 1,7-(4-(2,6-di-tert-butyl)phenol)-substituted aza-BODIPY core. The diradicaloids were by large array experimental computational methods. diamagnetic closed-shell state was postulated as ground in solution solid-state with substantial thermal population originating both open-shell diradical triplet states observed at room temperature. Transient absorption spectroscopy indicates fast (<10 ps) excited deactivation pathways associated target compounds' character Variable-temperature 1H NMR spectra indicate solvent dependency 5b. could be stepwise reduced to mixed-valence radical-anion dianion upon consequent single-electron reductions. Similarly, deprotonated aza-BODIPYs can oxidized form. Both dianionic forms exhibit an intense NIR region. Density functional theory (DFT) time-dependent DFT calculations used explain transformations UV–Vis-NIR all compounds.

Language: Английский

Halogenated Bis(donor)‐aza‐BODIPY System for Inducing NIR Excitation: Effect of Thiophene and Aminophenyl Donors on Optical Properties and in vitro Tests for Breast Cancer DOI

A. Verónica Rodríguez-Mayor,

Mario Rodríguez, Gabriel Ramos‐Ortíz

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(3)

Published: Jan. 1, 2025

Abstract A series of near‐IR absorbing BF 2 ‐chelated aza‐boron‐dipyrromethene (AZBs) derivatives bearing aniline/thiophene electron donors were designed, synthesized, and characterized to study the effect substitution on photophysical properties. These molecules exhibit internal charge transfer (ICT) with a characteristic spectrum dual absorption bands which allows electronic excitation in wide spectral region 500–820 nm. The ICT character was stablished by its inhibition upon protonation amino groups trifluoroacetic acid (TFA) CHCl 3 , observed as visible colorimetric change from red blue accompanied an hypsofluoric shift emission band. Protonation AZB‐4 DMSO‐ d 6 addition TFA monitored 1 H, 11 B, 19 F NMR. Thiophene Aza‐BODIPY p ‐(amino) phenyl also generated singlet oxygen ( O ) under irradiation laser light (532 800 nm). generation these dyes enhanced subsequent bromination molecule favors intersystem crossing between triplet states. aza‐BODIPY developed this work have potential applicability photosensitizers photodynamic therapy, sensibility window biomedical interest (700 – 900 nm) excellent photo chemical stability even at high energy irradiation. Additionally, their dark photoinduced cytotoxic activity tested breast cancer cell line (MDA‐MB‐231 cells).

Language: Английский

Citations

0
Synergism of rotary motor and twisted framework in NIR absorbing aza-BODIPY for photothermal-photodynamic therapy DOI
Yiming Zhang, Lei Fan,

Chuang Du

et al.

Materials Today Chemistry, Journal Year: 2025, Volume and Issue: 44, P. 102547 - 102547

Published: Jan. 25, 2025

Language: Английский

Citations

0
Synthesis, Spectral, and Computational Investigation of a New Red-Emissive BOIMPY DOI
Alexander A. Ksenofontov, М. Б. Березин, Pavel S. Bocharov

et al.

Journal of Fluorescence, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 4, 2025

Language: Английский

Citations

0
NIR-II absorbing aza-BODIPY with the D-A-A’ framework for PTT/PDT co-therapy DOI
Xin Zhang,

Ziyue Xi,

Dongxiang Zhang

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111041 - 111041

Published: March 1, 2025

Language: Английский

Citations

0
Near-Infrared emitting aza-BODIPY fluorophores, impact of N,N-dialkylamino groups on the photophysical properties: synthesis, characterization, and computational studies DOI

Wassima Tajani,

Ludmilla Verrieux,

Annika Sickinger

et al.

Dyes and Pigments, Journal Year: 2025, Volume and Issue: unknown, P. 112773 - 112773

Published: March 1, 2025

Language: Английский

Citations

0
Orthogonal configurative dye 2-anthryl asymmetric aza-BODIPY enhancing SOCT-ISC for phototherapy DOI

Shu Lv,

Xiuyan Gong,

Yunsheng Xue

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 111171 - 111171

Published: April 1, 2025

Language: Английский

Citations

0
Asymmetric and Symmetric S-zig-zag-Fused BODIPYs: Synthesis and Photophysical and Oxidative Properties DOI
Ruihan Yang, Li Lu,

Shulin Gao

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 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.

Language: Английский

Citations

0
WazaGaY: An Innovative Aza-BODIPY-Derived Near-Infrared Fluorescent Probe for Enhanced Tumor Imaging DOI

Mohamed Bendellaa,

Charlotte Cave,

Amélie Godard

et al.

Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 67(18), P. 16635 - 16648

Published: Sept. 17, 2024

Aza-BODIPYs represent a class of fluorophores in which the π-conjugated system is rigidified and stabilized by boron atom. A promising strategy to enhance their fluorescence properties involves replacing atom with metal ion. Here, we describe synthesis characterization water-soluble derivative where gallium(III) ion, termed WazaGaY (water-soluble aza-GaDIPY). Water solubility ensured two ammonium substituents, inducing bathochromic shift significant increase quantum yield compared that dimethylamino analog. The cellular behavior

Language: Английский

Citations

3
NIR-II emitting B,O-chelated twisted dye aza-BODIPY for phototherapy DOI

Yaqing Niu,

Qinsiyu Ma, Yikun Li

et al.

Dyes and Pigments, Journal Year: 2025, Volume and Issue: unknown, P. 112855 - 112855

Published: April 1, 2025

Language: Английский

Citations

0
Isolable Dipyrromethene‐Based Heavier Group 14 and 15 Element Complexes DOI

Qidi Bao,

Yuyang Dai,

Chen Liu

et al.

European Journal of Inorganic Chemistry, Journal Year: 2024, Volume and Issue: 27(10)

Published: Feb. 20, 2024

Abstract Boron‐dipyrromethenes (BODIPYs) have attracted much attention owing to their unique properties and widespread applications; however, the incorporation of heavier group 14 15 elements in rigid dipyrromethene ligands remains limited. Herein, dipyrromethene‐based element complexes, tin‐dipyrromethene (SNDIPY, 1 ) arsenic‐dipyrromethene (ASDIPY, 2 ), which are direct analogues BODIPY, been facilely synthesized isolated moderate yields. Both compounds investigated by NMR, UV‐vis absorption, photoluminescence spectroscopy, cyclic voltammogram, X‐ray crystallography, as well theoretical studies. exhibit green photoluminescence. Notably, SNDIPY is air‐stable compound represents first isolable structurally characterized ASDIPY.

Language: Английский

Citations

2