Tuning of Redox Potentials and LUMO Levels of BODIPYs via Site-Selective Direct Cyanation DOI

Huiquan Zuo,

Qinghua Wu, Xing Guo

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(45), P. 8150 - 8155

Published: Nov. 3, 2023

Through a strong oxidant Pb(OAc)4 promoted oxidative nucleophilic hydrogen substitution, site-selective direct and stepwise cyanation of BODIPYs using tetrabutylammonium cyanide was developed to give α-cyanated BODIPY derivatives. Characterization optical electrochemical properties these dyes provides substantial enhancement the electron affinity, with reduction potential LUMO level as low -0.04 V -4.43 eV, respectively. Radical anions electron-deficient 3,5-dicyanated were characterized by absorption EPR spectroscopy.

Language: Английский

Oxidation-State-Dependent Photochemistry of Sulfur-Bridged Aza-Anthracenes DOI
Ryoga Hojo, H. Noguchi, Jéssica Toigo

et al.

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

Published: April 16, 2025

Aromatic systems with bridged sulfur units in varying oxidation states have enabled photoresponsive materials for anticounterfeiting and supramolecular assembly. However, only a few sulfoxide-bridged chromophores exhibit photoinduced extrusion, leading to drastic photophysical changes that make them useful as stimuli-responsive materials. Here, we present nitrogen-substituted anthracene (aza-anthracene) bridge different states. Overall, aza-anthracene produces red-shifted green-to-red similar sulfoxide photoconversion behavior compared the analog.

Language: Английский

Citations

0

Developments of the mDZ-RhoBAST Probe for Super-Resolution Imaging of FTO Demethylation in Live Cells DOI
Xiaolu Zhou,

Huihui Gao,

Limin Xiang

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 28, 2025

Single-molecule localization microscopy (SMLM) provides precise, high-resolution visualization of target biomolecules in cellular imaging. Fluorescent light-up aptamers (FLAPs) offer a versatile approach for labeling RNA interest live cells by binding to fluorogens through adaptive recognition. Several FLAPs can generate blinking fluorescent signals conjunction with fluorogens, enabling single-molecule imaging living cells. An example this is RhoBAST, which has been successfully used due its fast exchange kinetics fluorogens. However, activities regulated proteins presents greater challenge. Here, we introduce mDZ-RhoBAST, nucleic acid probe, visualize the demethylation process fat mass and obesity-associated protein (FTO) This probe combines 6mA-modified DNAzyme RhoBAST FLAP, activated FTO, restoring DNAzyme's cleavage activity releasing bind fluorogen. Our achieved super-resolution endogenous providing real-time insights into processes vivo.

Language: Английский

Citations

0

Visible-Light-Induced Direct Photoamination of BODIPY Dyes with Aqueous Ammonia DOI
Dandan Wang, Long Wang, Xing Guo

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(42), P. 7650 - 7655

Published: Oct. 13, 2023

By taking advantage of their strong absorption ability, visible-light-induced direct photoamination BODIPY dyes with aqueous ammonia was developed to give structurally diverse α-amino BODIPYs. The excited state BODIPYs possessed higher electron affinity than the ground and thus showed largely enhanced reactivity toward weak nucleophile ammonia. Those are valuable synthetic intermediates have been successfully demonstrated in several post-transformation reactions. work indicates that photoreaction is an excellent alternative conventional functionalization this popular fluorophore.

Language: Английский

Citations

9

Tuning Directed Photooxidation‐Induced Conversion of Pyrrole‐Based Styryl Coumarin Dual‐Color Photoconverters DOI Creative Commons
Lazare Saladin, Ophélie Dal Pra, Andrey S. Klymchenko

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(20)

Published: Jan. 31, 2023

Dual-emissive photoconvertible fluorophores (DPCFs) are powerful tools to unambiguously track labeled cells in bioimaging. We recently introduced a new rational mechanism called directed photooxidation-induced conversion (DPIC) enabling efficient DPCFs be obtained by conjugating coumarin aromatic singlet-oxygen reactive moieties (ASORMs). Pyrrole was found suitable ASORM as it provided high hypsochromic shift along with fast and conversion. By synthesizing various pyrrole-based styryl dyes, we showed that the photoconversion properties, including quantum yield of chemical can tuned modification pyrrole. These modifications led an improved dual emissive converter, SCP-Boc, which displayed brightness enhanced 63 %. SCP-Boc successfully used sequentially photoconvert laser scanning confocal microscopy.

Language: Английский

Citations

8

Tuning of Redox Potentials and LUMO Levels of BODIPYs via Site-Selective Direct Cyanation DOI

Huiquan Zuo,

Qinghua Wu, Xing Guo

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(45), P. 8150 - 8155

Published: Nov. 3, 2023

Through a strong oxidant Pb(OAc)4 promoted oxidative nucleophilic hydrogen substitution, site-selective direct and stepwise cyanation of BODIPYs using tetrabutylammonium cyanide was developed to give α-cyanated BODIPY derivatives. Characterization optical electrochemical properties these dyes provides substantial enhancement the electron affinity, with reduction potential LUMO level as low -0.04 V -4.43 eV, respectively. Radical anions electron-deficient 3,5-dicyanated were characterized by absorption EPR spectroscopy.

Language: Английский

Citations

8