ABSTRACT
Typical aggregation-induced emission enhancement fluorogens (AIEEgens) generally are designed as propeller-shaped molecules with multiple aromatic rotors. Described herein are 1,4-dihydropyridines, which have the minimum size necessary for AIEE, containing only a single ring, synthesized through a facile biocatalysis procedure. Owing to the AIEE property, intramolecular motion can be restrained by the surrounding environment, causing the radiative channel to open up. Both the fluorescence intensities and the lifetimes of the 1,4-dihydropyridine representatives increased with increasing viscosity, and high sensitivities were observed. On the basis of the single crystal X-ray structures, density functional theory (DFT) calculations were performed to explain the mechanism of the single-ring AIEE behaviour. Moreover, a few of the neutral AIEEgens were found to possess a high specificity towards mitochondria. As an example, one of the AIEEgens exhibited superior photostability and excellent storage tolerance, allowing for real-time imaging, viscosity mapping, and long-term tracking of the dynamics of the mitochondrial morphology.
ABSTRACT
We presented a novel approach for pyrophosphate (PPi) sensing. Two tetraphenylethene (TPE)-functionalised pyridine salts (TPM and TPH) were designed and synthesized. Both of them exhibited weak emission in the solution state that originates from intramolecular charge transfer (ICT) from TPE to the pyridine; the addition of PPi into the TPM aqueous solution would enhance the fluorescence intensity, which eliminates the emission quenching effect of the iodide ion by the formation of PPi-sensor nanoparticles. The detection limit of TPM was determined to be as low as 133 nM. Meanwhile, a thin solid film of TPM that could detect PPi rapidly was conveniently prepared.
Subject(s)
Diphosphates/analysis , Fluorescent Dyes/chemistry , Pyridines/chemistry , Salts/chemistry , Stilbenes/chemistry , Chemistry Techniques, Analytical , Diphosphates/chemistry , HeLa Cells , Humans , Limit of Detection , Spectrometry, FluorescenceABSTRACT
The terpyridine anthracene ligand was synthesized and characterized. is a ratiometric fluorescent probe for Cd(2+) with a recognition mechanism based on intramolecular charge transfer (ICT). An complex was isolated, and its structure was established using single-crystal XRD. The complex was able to serve as a novel reversible chemosensing ensemble to allow ratiometric response to pyrophosphate (PPi) in aqueous media. Moreover, the fluorescence imaging in living cells from these two emission channels suggested that was a ratiometric probe for Cd(2+), and the in situ generated complex was also a ratiometric ensemble for PPi detection in living cells.
Subject(s)
Cadmium/chemistry , Coordination Complexes/chemistry , Diphosphates/analysis , Fluorescent Dyes/chemistry , Microscopy, Confocal , Spectrometry, Fluorescence , Animals , Cell Line , Coordination Complexes/chemical synthesis , Coordination Complexes/metabolism , Crystallography, X-Ray , Mice , Molecular Conformation , Pyridines/chemistry , Solutions/chemistryABSTRACT
An in situ generated BINOL-DPA-Zn(ii) complex is presented as a chemo-sensing ensemble for the recognition of phosphate-based molecules. The ensemble showed high sensitivity and selectivity for pyrophosphates (PPi), and it could be successfully applied in imaging PPi in living cells. Notably, the ensemble exhibited a very low detection limit (95 nM) for PPi and could realize the real time detection of PPi by the naked eye through precipitate experiments. The ensemble also showed good selectivity towards ATP, and the selectivity coefficient for PPi and ATP was calculated to be 4.1/2.8.
Subject(s)
Diphosphates/analysis , Fluorescent Dyes/chemistry , Organometallic Compounds/chemistry , Fluorescent Dyes/chemical synthesis , HeLa Cells , Humans , Models, Molecular , Molecular Structure , Organometallic Compounds/chemical synthesis , Particle Size , Solutions , Surface Properties , Time Factors , Water/chemistry , Zinc/chemistryABSTRACT
A novel BINOL-based ratiometric fluorescent sensor (R2) is presented, which can selectively respond to Zn(2+) over Cd(2+) and other metal ions with fluorescence enhancement in aqueous solution. The R2 was successfully applied in the imaging of Zn(2+) in living cells. Additionally, the in situ generated R2-Zn(II) ensemble could further serve as a probe to distinguish histidine from other amino acids via a displacement mode.
