Fluorescent 5H‐Pyrano[3,2‐c]chromenes: Synthesis, Photophysical Properties and Sensing of Nucleophilic Anions DOI
N. M. Chernov, Maxim S. Panov,

Mariya Yu. Domotskaya

et al.

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(4)

Published: Jan. 26, 2024

Abstract We report the development of a convenient organocatalytic method for synthesis 5 H ‐pyrano[3,2‐ c ]chromenes from chromone‐containing acrylates and ethyl cyanoacetate. The is characterized by simple conditions (ethanol, basic catalysis) good yields (up to 90 %). synthesized pyrano[3,2‐ are promising new class fluorescent compounds. They have intense fluorescence in yellow‐green region spectrum (495–554 nm) with high quantum 72 %) exhibit large Stokes shifts (3514–5856 cm −1 ). demonstrated possible application obtained as selective “turn‐off” sensors nucleophilic anions, such cyanide, sulfide sulfite.

Language: Английский

Organic Fluorophores with Large Stokes Shift for Bioimaging and Biosensing DOI
Hong Liu, Gangwei Jiang, Guoliang Ke

et al.

ChemPhotoChem, Journal Year: 2023, Volume and Issue: 8(5)

Published: Dec. 14, 2023

Abstract Fluorophores and fluorophores‐based probes or labels can visualize the structures content fluctuations of biomolecules, have made great progress in broad range biomedicine fields. However, many commercially available fluorophores suffer from small Stokes shift, which results insufficient signal‐to‐noise ratio self‐quenching advanced imaging techniques. Moreover, shift also hinders application some complex imaging, such as single‐excitation multicolor imaging. In past two decades, effects been to enlarge fluorophores. this review, we clarified reasons for building on structural analysis fluorophores, systematically summarize methods modification increase present representative applications with large sensing.

Language: Английский

Citations

15

Dithienoazepine‐Based Near‐Infrared Dyes: Janus‐Faced Effects of a Thiophene‐Fused Structure on Antiaromatic Azepines DOI Creative Commons
Masahito Murai, Takahiro Enoki, Shigehiro Yamaguchi

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(49)

Published: Sept. 13, 2023

We here disclose that the incorporation of thiophene rings into a seven-membered 8π azepine in fused fashion produces useful antiaromatic core for near-infrared (NIR) dyes. In contrast to dibenzazepine derivatives with bent structures, dithieno-fused electron-accepting groups adopt flat conformations ground state. The exhibited broad absorption spectra cover visible region as well sharp emission bands NIR region, which are considerably red-shifted relative those dibenzo-fused congeners. Theoretical study revealed two contradictory effects less-aromatic thiophene-fused structure, i.e., enhancement antiaromaticity adjacent ring and relief through contribution quinoidal resonance form. combination dithienoazepine cationic produced fluorescent dye an at 878 nm solution.

Language: Английский

Citations

14

Recent advances in the development of fluorescent probes for γ‐glutamyltranspeptidase DOI

Ze-Yang Hu,

Xuyang Chen, Yu‐Shun Yang

et al.

Coordination Chemistry Reviews, Journal Year: 2023, Volume and Issue: 501, P. 215562 - 215562

Published: Nov. 27, 2023

Language: Английский

Citations

11

Ultrabright Dibenzofluoran‐Based Polymer Dots with NIR‐IIa Emission Maxima and Unusual Large Stokes Shifts for 3D Rotational Stereo Imaging DOI Creative Commons
P. Chowdhury,

Zhao‐Yu Lu,

Shih‐Po Su

et al.

Advanced Healthcare Materials, Journal Year: 2024, Volume and Issue: 13(20)

Published: April 29, 2024

Emerging organic molecules with emissions in the second near-infrared (NIR-II) region are garnering significant attention. Unfortunately, achieving accountable emission intensity over NIR-IIa (1300 nm) faces challenges due to intrinsic energy gap law. Up current stage, all reported emitters belong polymethine-based dyes small Stokes shifts (<50 and low quantum yield (QY; ≤0.015%). However, such polymethines have proved cause self-absorption constrained brightness, limiting advanced development deep-tissue imaging. Here a new scaffold based on rigid highly conjugated dibenzofluoran core terminated by amino-containing moieties that reveal peaks of 1230-1305 nm is designed. The QY at least 10 times higher than synthesized or extraordinarily large 370-446 nm. DBF-BJ further prepared as polymer dot demonstrate its vivo 3D stereo imaging mouse vasculature 1400 long-pass filter.

Language: Английский

Citations

4

Molecular Engineering of 2′, 7′‐Dichlorofluorescein to Unlock Efficient Superoxide Anion NIR‐II Fluorescent Imaging and Tumor Photothermal Therapy DOI Open Access
Lizhen Xu, Xin Wang, Ling Huang

et al.

Small, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 12, 2025

Abstract Although classical fluorescent dyes feature advantages of high quantum yield, tunable “OFF‐ON” fluorescence, and modifiable chemical structures, etc., their bio‐applications in deep tissue remains challenging due to excessively short emission wavelength (that may lead superficial penetration depth). Therefore, there is a pressing need for pushing the from visible region NIR‐II window. As representative dye, 2′,7′‐Dichlorofluorescein ( DCF ), derivative Fluorescein, selected rationally engineered develop novel platform, CR‐OH , which exhibits substantial red‐shift region. This achievement attributed molecular modification strategies that include extending π‐conjugation, enhancing rigidity, incorporating strong electron‐withdrawing groups. Furthermore, based on this developed fluorescence probe photothermal nanoagent are successfully constructed unlock its bio‐application imaging endogenous O 2 ·– fluctuations CIRI model first time, as well effective therapy 4T1 tumors with conversion efficiency (44.0%). Significantly, work overcomes limitation dyes, effectively unlocking applications diagnosis treatment early disease

Language: Английский

Citations

0

Design, Synthesis, and In Vivo Imaging of a Stable Xanthene-Based Dye with NIR-II Emission up to 1450 nm DOI
Xi Gao, Jinyu Wang,

Yufei Qin

et al.

Analytical Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 15, 2025

The development of long-wavelength near-infrared II (NIR-II, 900–1700 nm) dyes is highly desirable but challenging. To achieve both red-shifted absorption/emission and superior in vivo imaging capabilities, a donor–acceptor–donor (D–A–D) xanthene core was strategically modified by extending π-conjugated double bonds enhancing electron-donating properties. Two named VIX-1250 VIX-1450 were synthesized exhibited notably peaks at 942/1250 1098/1450 nm, respectively. Among them, demonstrated chemo- photostability even such long wavelengths. Fluorescent angiography using micelles enabled high-clarity blood vessel with remarkable signal-to-noise ratio (SNR), underscoring that the dye's large Stokes shift (352 nm), good brightness (13 M–1 cm–1), wavelength served as key factors for high-quality biosensing. Additionally, combined ICG dual-color achieved near-zero optical cross talk, enabling different organ labeling. This study provides new direction design organic dyes.

Language: Английский

Citations

0

Paper and Pencil Design of Color-Pure Organic Emitters: The Curious Case of Xanthene Dyes DOI

Morteza Eskandari,

Liangxuan Wang, Begoña Milián‐Medina

et al.

The Journal of Physical Chemistry A, Journal Year: 2025, Volume and Issue: 129(6), P. 1599 - 1608

Published: Jan. 31, 2025

The quest for color-pure emitters multicolor bioimaging as well ultrahigh definition organic light-emitting diodes demands facile design concepts to avoid tedious synthetic or computational trial-and-error procedures. We have recently presented a simple recipe construct blue emitters, which combines basic resonance structure and frontier molecular orbital treatments; this applies multiresonant type allows enlarge the chemical space toward novel structural motifs. In current work, we show that such fundamental considerations further apply structurally entirely different family of xanthene dyes. Opposite related polymethine dye with small bond length alternation (BLA) in ground excited state (S0, S1), however, dyes display large BLA S0 S1, so overall change BLA, ΔBL, is small. This gives equally rise emission; underlying reasons curious behavior are carved out study. generalization fact constitutes desired "paper pencil" strategy, spanning now whole visible range.

Language: Английский

Citations

0

Architecture design of improved near-infrared hemicyanine dyes for biosensing and bioimaging DOI

Guohui Deng,

Gangwei Jiang, Lin Yuan

et al.

Chinese Science Bulletin (Chinese Version), Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Language: Английский

Citations

0

A cyanine fluorophore for imaging-guided tumor photodynamic and photothermal therapy under NIR-II light activation DOI
Wenkai Liu,

Chengyuan Lv,

Yanxian Hou

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 10, 2025

Language: Английский

Citations

0

Development and Application of Organic Sonosensitizers in Cancer Therapy DOI Creative Commons
Yuhan Ding,

Yuchen Yang,

Ömer Aras

et al.

Aggregate, Journal Year: 2025, Volume and Issue: unknown

Published: April 11, 2025

ABSTRACT Sonodynamic therapy (SDT) is an innovative cancer modality that harnesses the energy of ultrasound to activate sonosensitizers for producing reactive oxygen species (ROS), culminating in eradication tumor cells. Compared with photodynamic therapy, SDT has capacity penetrate deeply into biological tissues, thereby holding significant promise addressing situated or surgically inaccessible tumors. The effectiveness greatly dependent on characteristics sonosensitizers, and unlike inorganic organic offer a more controlled synthesis process have excellent biocompatibility. This review presents meticulous undertaking categorize elucidate their mechanisms action therapeutic effects context SDT. Design strategies are also summarized, we emphasize critical role nanotechnology localization, imaging, multimodal synergistic offering approach achieving precise targeting. In addition, impact delineated when integrated other oncological modalities, such as photothermal enhance efficacy. Finally, discusses challenges future perspectives advancement clinical within realm oncology.

Language: Английский

Citations

0