Anion Sensing through Redox‐Modulated Fluorescent Halogen Bonding and Hydrogen Bonding Hosts** DOI Creative Commons
Andrew J. Taylor, Robert Hein, Sophie C. Patrick

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 136(6)

Published: Dec. 8, 2023

Abstract Anion sensing via either optical or electrochemical readouts has separately received enormous attention, however, a judicious combination of the advantages both modalities remains unexplored. Toward this goal, we herein disclose series novel, redox‐active, fluorescent, halogen bonding (XB) and hydrogen (HB) BODIPY‐based anion sensors, wherein introduction ferrocene motif induces remarkable changes in fluorescence response. Extensive titration, lifetime studies reveal binding‐induced emission modulation through intramolecular photoinduced electron transfer (PET), magnitude which is dependent on nature XB/HB donor anion. Impressively, XB sensor outperformed its HB congener terms binding strength switching magnitude, displaying significant turn‐OFF upon binding. In contrast, redox‐inactive control receptors display turn‐ON response, highlighting pronounced impact redox‐active performance. Additionally, also serves as an reporter group, enabling voltammetric competitive solvents. The combined were further exploited proof‐of‐principle, spectroelectrochemical approach, simultaneous sensitive read out responses multiple oxidation states at very low receptor concentration.

Language: Английский

Macrocyclic Conformational Switch Coupled with Pyridinium-Induced PET for Fluorescence Detection of Adenosine Triphosphate DOI
Boris S. Morozov,

Fabiano Gargiulo,

Swapnil Ghule

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(10), P. 7105 - 7115

Published: Feb. 28, 2024

The binding of nucleotides is crucial for signal transduction as it induces conformational protein changes, leading to downstream cellular responses. Synthetic receptors that bind and transduce the event into global rearrangements are highly challenging design, especially those operate in an aqueous solution. Much work focused on evaluating functionalized dyes detect nucleotides, whereas coupling a nucleotide-induced switching sensing has not been reported date. We disclose synthetic undergo rearrangement upon nucleotide binding. Integrating naphthalimide pyridinium ion structure enables stabilization folded conformation efficient fluorescence quenching. rearranges receptor alters strong enhancement. methylpyridinium-containing demonstrated high selectivity adenosine 5′-triphosphate (ATP) record 160-fold It can fluctuations ATP HeLa cells possesses low cytotoxicity. developed systems present attractive approach designing ATP-responsive artificial molecular switches water integrate response.

Language: Английский

Citations

10
Recent applications of organic cages in sensing and separation processes in solution DOI Creative Commons
Sonia La Cognata, Valeria Amendola

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(92), P. 13668 - 13678

Published: Jan. 1, 2023

Cages at work: structural tunability results in tailored properties, which makes these systems suitable for countless applications sensing and separation processes, both solution the solid state.

Language: Английский

Citations

22
Quinolinium-Based Fluorescent Probes for Dynamic pH Monitoring in Aqueous Media at High pH Using Fluorescence Lifetime Imaging DOI Creative Commons
Jorrit Bleeker,

Aron P. Kahn,

Lorenz M. Baumgartner

et al.

ACS Sensors, Journal Year: 2023, Volume and Issue: 8(5), P. 2050 - 2059

Published: April 27, 2023

Spatiotemporal pH imaging using fluorescence lifetime microscopy (FLIM) is an excellent technique for investigating dynamic (electro)chemical processes. However, probes that are responsive at high values not available. Here, we describe the development and application of dedicated based on 1-methyl-7-amino-quinolinium fluorophore. The quantum yield, (photo)stability, inherent water solubility make quinolinium fluorophore well suited FLIM probes. Due to flexible fluorophore-spacer–receptor architecture, probe lifetimes tunable in range between 5.5 11. An additional response, 11 13, achieved by deprotonation aromatic amine core. Probe hardly affected temperature presence most inorganic ions, thus making highly reliable convenient. At 0.1 mM concentrations, rates 3 images per second, a resolution 4 μm, while measuring up 12 achieved. This enables electrochemical processes involving chemical reactions mass transport.

Language: Английский

Citations

14
Anion Sensing through Redox‐Modulated Fluorescent Halogen Bonding and Hydrogen Bonding Hosts** DOI Creative Commons
Andrew J. Taylor, Robert Hein, Sophie C. Patrick

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 63(6)

Published: Dec. 8, 2023

Abstract Anion sensing via either optical or electrochemical readouts has separately received enormous attention, however, a judicious combination of the advantages both modalities remains unexplored. Toward this goal, we herein disclose series novel, redox‐active, fluorescent, halogen bonding (XB) and hydrogen (HB) BODIPY‐based anion sensors, wherein introduction ferrocene motif induces remarkable changes in fluorescence response. Extensive titration, lifetime studies reveal binding‐induced emission modulation through intramolecular photoinduced electron transfer (PET), magnitude which is dependent on nature XB/HB donor anion. Impressively, XB sensor outperformed its HB congener terms binding strength switching magnitude, displaying significant turn‐OFF upon binding. In contrast, redox‐inactive control receptors display turn‐ON response, highlighting pronounced impact redox‐active performance. Additionally, also serves as an reporter group, enabling voltammetric competitive solvents. The combined were further exploited proof‐of‐principle, spectroelectrochemical approach, simultaneous sensitive read out responses multiple oxidation states at very low receptor concentration.

Language: Английский

Citations

14
Synthesis and fluorescent properties of 2ʹ-benzyloxy flavone-a dual probe for selective detection of picric acid and pH sensing DOI Creative Commons

Vengatesh Gopal,

Jayasankar Sudhakaran,

Nirenjana Ramachandran

et al.

Sensors & Diagnostics, Journal Year: 2024, Volume and Issue: 3(8), P. 1263 - 1271

Published: Jan. 1, 2024

2′-Benzyloxy flavone as a novel dual fluorescent probe for picric acid and pH sensing.

Language: Английский

Citations

4
Thiourea-Based Receptors for Anion Recognition and Signaling DOI Creative Commons
Jancarlo Gómez-Vega,

Adrian Vasquez-Cornejo,

Octavio Juárez-Sánchez

et al.

ACS Omega, Journal Year: 2024, Volume and Issue: 9(4), P. 4412 - 4422

Published: Jan. 17, 2024

This work reports on two thiourea-based receptors with pyridine and amine units including 1-naphthyl (MT1N) 4-nytrophenyl (MT4N) as signaling units. For both compounds, their affinity ability toward various anions of different geometry basicity in DMSO were studied using UV–vis, fluorescence, 1H NMR techniques. Anion recognition studies revealed that MT1N MT4N have, general, high affinities basic anions. In this regard, a higher acidity the receptor was demonstrated. Furthermore, has for fluoride (log K1 = 5.98) than other can effectively detect it through colorimetric changes be monitored by UV–vis technique. The interaction between mainly involves hydrogens amino thiourea groups former. Complementary single-crystal X-ray diffraction molecular modeling at DFT level also performed.

Language: Английский

Citations

3
Cinchona alkaloids – acid, anion-driven fluorescent INHIBIT logic gates with a receptor1–fluorophore–spacer–receptor2 format and PET and ICT mechanisms DOI Creative Commons
Nicola’ Agius, David C. Magri

RSC Advances, Journal Year: 2023, Volume and Issue: 13(20), P. 13505 - 13510

Published: Jan. 1, 2023

The fluorescent natural products quinine, quinidine, cinchonine and cinchonidine are demonstrated as H + -enabled, halide-disabled (Cl − , Br or I ) INHIBIT logic gates in water.

Language: Английский

Citations

9
Rational Design of the β‐Bulge Gate in a Green Fluorescent Protein Accelerates the Kinetics of Sulfate Sensing** DOI
Whitney S. Y. Ong, Ke Ji, Vishaka Pathiranage

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(26)

Published: April 15, 2023

Detection of anions in complex aqueous media is a fundamental challenge with practical utility that can be addressed by supramolecular chemistry. Biomolecular hosts such as proteins used and adapted an alternative to synthetic hosts. Here, we report how the mutagenesis β-bulge residues (D137 W138) mNeonGreen, bright, monomeric fluorescent protein, unlocks tunes anion preference at physiological pH for sulfate, resulting turn-off sensor SulfOFF-1. This unprecedented sensing arises from enhancement kinetics binding, largely driven position 138. In line these data, molecular dynamics (MD) simulations capture coordinated entry gating sulfate into β-barrel eliminated upon facilitate binding fluorescence quenching.

Language: Английский

Citations

8
A Semiflexible Tetrahydrazone Macrocycle for Binding of Pyrophosphate and Smaller Anions DOI
Lau Halgreen, Aarón Torres‐Huerta, Karolis Norvaiša

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 6853 - 6864

Published: April 25, 2024

Macrocyclization has proven to be a useful design strategy in the development of efficient anion receptors. In addition ring size, overall preorganization due structural rigidity is key. To explore this context developing an pyrophosphate receptor, three macrocycles featuring 26-membered interior size and similar H-bonding motifs have been synthesized, their binding ability investigated. Computational studies nuclear magnetic resonance (NMR) data showed different degrees as result differences flexibility. The interaction with chloride, dihydrogen phosphate, was investigated solution by NMR ultraviolet–visible spectroscopy solid state X-ray crystallography. tetrahydrazone-based macrocycle intermediate flexibility exhibited best affinity for all anions Our results suggest that proper groups certain degree also required optimal target guest.

Language: Английский

Citations

2
A semi-flexible tetrahydrazone macrocycle for binding of pyrophosphate and smaller anions DOI Creative Commons
Lau Halgreen, Aarón Torres‐Huerta, Karolis Norvaiša

et al.

Published: Jan. 25, 2024

Macrocyclization has proven to be a useful design strategy in the development of efficient anion receptors. In addition ring size, overall preorganization by structural rigidity is key importance. To explore this context developing an pyrophosphate receptor, three macrocycles featuring 26-membered interior size and similar H-bonding motifs have been synthesized their binding ability investigated. Computational studies NMR data showed different degrees as result differences flexibility. The interaction with chloride, dihydrogenphosphate, dihydrogen was investigated solution UV-Vis spectroscopy, solid state X-ray crystallography. tetrahydrazone based macrocycle intermediate flexibility exhibited best affinity for all anions Our results suggest that proper groups certain degree also required optimal target guest.

Language: Английский

Citations

1