Synthesis, Structure, Spectral, and Electrochemical Properties of New Visible to NIR Absorbing 3-Pyrrolyl BODIPY Derivatives DOI
Kanhu Charan Behera,

Pinky Chauhan,

Shubham Tiwari

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 3, 2024

This study presents 3-pyrrolyl BODIPY-based Schiff base and benzothiazole derivatives with tunable red-to-NIR properties, highlighting a Re( i ) complex distorted octahedral geometry for its potential in coordination chemistry.

Language: Английский

Synthesis and properties of covalently linked phenyl bridged 3-pyrrolyl BODIPY–BODIPY dyads DOI

Abani Sarkar,

Kanhu Charan Behera,

Ankit Tumsare

et al.

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(12), P. 5362 - 5371

Published: Jan. 1, 2024

Two different covalently linked 3-pyrrolyl BODIPY–BODIPY dyads were synthesized and their fluorescence studies indicated a possibility of singlet–singlet energy transfer from BODIPY to unit.

Language: Английский

Citations

4
Synthesis of Novel Fluorescent 3-Pyrrolyl BODIPYs and Their Derivatives DOI Creative Commons

Vratta Grover,

Mangalampalli Ravikanth

Tetrahedron Chem, Journal Year: 2025, Volume and Issue: unknown, P. 100121 - 100121

Published: Jan. 1, 2025

Language: Английский

Citations

0
N, O - Chelate Fluoroborane Dyes: Synthesis, Optical Properties in Dual Aggregate State DOI
Yangyang Liu, Debao Liu, Nuonuo Zhang

et al.

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

Published: April 23, 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
BODIPY: synthesis, modification, and applications in sensing and biomedicine DOI

Daniil Spector,

Daniil Abramchuk,

Vladislav Bykusov

et al.

Russian Chemical Reviews, Journal Year: 2024, Volume and Issue: 93(10), P. RCR5136 - RCR5136

Published: Oct. 1, 2024

BODIPY chromophores (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) are one of the most versatile fluorophores which commonly used in a variety scientific fields. The combination excellent photophysical properties with possibility easy chemical modification structure, and photostability determines application biomedicine, photocatalysis, analytical chemistry materials science. This review summarizes approaches to synthesis BODIPY, discussing both classical recently-published synthetic postfunctionalization approaches. An influence structure various methods on their potential applications science biosensorics also discussed.<br> bibliography includes 344 references.

Language: Английский

Citations

2
Chemoselective reaction of methoxyaminomethyl BODIPYs with unprotected carbohydrates: a powerful tool for accessing BODIPY neoglycosides DOI Creative Commons
Ana M. Gómez, Luis García‐Fernández, Andrés G. Santana

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(16), P. 4356 - 4365

Published: Jan. 1, 2024

The neoglycosylation of methoxyaminomethyl BODIPYs with unprotected reducing saccharides produces cyclic N -glycosyl- -methoxy-BODIPY conjugates, which display excellent photophysical characteristics in pure water, even at high dye concentrations.

Language: Английский

Citations

1
Synthesis of Pyridyl Functionalized 3-Pyrolyl BODIPY based Fluoroprobes and Application Towards Highly Selective Detection of Picric Acid DOI

Debendra Tewary,

Kanhu Charan Behera, David R. Turner

et al.

Physical Chemistry Chemical Physics, Journal Year: 2024, Volume and Issue: 26(34), P. 22479 - 22490

Published: Jan. 1, 2024

A series of pyridyl-coupled 3-pyrrolyl BODIPY fluoroprobes were synthesized by varying the position pyridyl/

Language: Английский

Citations

1
Synthesis and Properties of Tris(3‐Pyrrolyl BODIPY) on 1, 3, 5‐Triazine Scaffold DOI
Kanhu Charan Behera, Mangalampalli Ravikanth

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(42)

Published: Aug. 14, 2024

Abstract Tris(3‐pyrrolyl BODIPY) on 1,3,5‐triazine scaffold was synthesized over a sequence of steps starting from commercially available cyanuric chloride. The chloride reacted with p‐hydroxy benzaldehyde to afford tris(p‐oxybenzaldehyde) which then excess pyrrole under acid catalyzed conditions 1,3,5‐triazine‐tris(meso‐p‐oxyphenyl dipyrromethane). Subsequent in situ oxidation this compound DDQ obtain tris(meso‐oxyphenyldipyrromethene) treated followed by the addition Et 3 N/BF ⋅ OEt 2 afforded fluorescent tris(3‐pyrrolyl BODIPY). For comparison, tris(BODIPY) triazine prepared oxidizing tris(meso‐oxyphenyldipyrromethane) complexation BF . Both compounds were thoroughly characterized and studied various experimental theoretical methods. Absorption, steady state fluorescence, time‐resolved transient‐absorption studies revealed that BODIPY), excitonic interactions between two three 3‐pyrrolyl BODIPY units resulted hypsochromic shift spectral bands, reducing quantum yield singlet lifetime whereas did not show such interactions. DFT helped understanding both solution solid state. viscosity indicated fluorescence increases significantly solvent viscosity, suggesting its potential for measuring cellular during physiological processes.

Language: Английский

Citations

1
Efficient light-induced reactive oxygen species production from a far-red ER-targeting BODIPY dye DOI Creative Commons
Shawn Swavey, Arnaud Quentel,

Matthew Grzesiak

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(52), P. 38796 - 38805

Published: Jan. 1, 2024

Generation of reactive oxygen species (ROS) within the ER evokes stress leading to immunogenic cell death. A red light activated BODIPY dye capable subcellular localization producing high quantum yields ROS is reported. The ability this act as a photodynamic therapy (PDT) agent in breast cancer cells suggests promising organelle-targeted therapeutics.

Language: Английский

Citations

1
Near-Infrared Persistent Luminescence of CaTiO3:Cr,Y for Imaging of Bone Implants Using Red-Light Illumination Instead of X-ray DOI

Yicheng Xu,

Gulizhabaier Abulipizi,

Yuxin Wang

et al.

ACS Applied Materials & Interfaces, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 5, 2024

Near-infrared (NIR) persistent luminescence (PersL) materials have unique optical properties with promising applications in bioimaging and anticounterfeiting. However, their development is currently hindered by poor red-light-exciting ability. In this study, CaTiO3:Cr0.001,Y0.02 (CTCY) was synthesized 650 nm-excited 772 nm NIR PersL. The Y3+ doping the Ca2+ lattice plays a key role PersL property. A charge compensation mechanism proposed, which Cr3+ Ti4+ stabilized Y3+-doping while oxygen vacancies were generated to store excitation energy at same time. thermal ionization might elucidate red-light-excited of CTCY, benefits from perovskite structure CaTiO3. CTCY has 120 times more intense than Zn3Ga2Ge2O10:Cr. Its potential anticounterfeiting demonstrated using visible/NIR dual-channel flower painting CTCY-labeled bone screw for situ reactivable imaging red light illumination instead X-ray, respectively. This study not only provides new material but also will add our understanding developing other red-light- or even NIR-activable perovskite-like structures.

Language: Английский

Citations

0