Preparation, regulation and biological application of a Schiff base fluorescence probe

Two new Macroacyclic Schiff base chemosensors (L1 and L2) were synthesized by the one pot condensation reaction of 2‐[3‐(2‐formyl phenoxy)propoxy]benzaldehyde and aminophenol in a 1:2 molar ratio and were characterized by IR, NMR spectroscopy. Both Schiff bases displayed high selectivity and sensitivity towards Fe3+ over other metal ions in H2O‐DMF solution (Ag+,Cu2+, Ni2+, Zn2+, Mg+2, Mn+2, Pb+2, Co+2, Hg+2, Cr+3, Na+, Ba+2 and Cd2+) due to their structure including oxygen donor atoms. The test results showed fluorescence quenching of the fluorophores when Fe3+ was bound to the recognition units. From test results, a high selectivity for Fe3+ were discovered in this type of sensors, especially, the probe based on 2‐aminophenol exhibited more significant quenching in fluorescence intensity compared with 4‐aminophenol‐based due to its rigidity structure. In addition, the structure of ligands and their antibacterial properties was investigated.

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Selective and Sensitive Two New Macroacyclic Schiff base Fluorescent Turn‐Off Receptors for Fe³⁺, DFT Calculation and Their Antibacterial Activity

Ooshall

Golbedaghi

Jamehbozorgi

2020

Applied Organom Chemis

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A highly selective and sensitive turn‐on fluorescent probe for the detection of Al³⁺ and its bioimaging

et al. 2016

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A novel fluorescent sensor, 1-((2-hydroxynaphthalen-1-yl)methylene)urea (ocn) has been designed and applied as a highly selective and sensitive fluorescent probe for recognition of Al in Tris-HCl (pH = 7.20) solution. The probe ocn exhibits an excellent selectivity to Al over other examined metal ions, anions and amino acids with a prominent fluorescence 'turn-on' at 438 nm. ocn binds to Al with a 2:1 binding stoichiometry and the detection limit was 0.3 μM. Furthermore, its capability of biological application was evaluated and the results showed that the sensor could be used to detect Al in living cells.

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Influences of polarizability effect of alkyl group and homoring competition effect of substituents on the fluorescence emission spectra of salen‐type Schiff bases

Wei¹,

Cao²

2021

J of Physical Organic Chem

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To explore the effect of substituent attached to aromatic ring and the length of diamine chain in salen-type Schiff base molecules on the fluorescence emission spectra (FL em ), the FL em of 63 diamine-salicylaldehyde condensates in an ethanol solution were obtained. The influence of substituent electronic effects and chain lengths on the wavenumber (ν em ) of fluorescence emission wavelengths (λ em ) was subsequently studied. The results show that the length of the diamine chain in the target compound has an effect on the ν em , which can be quantified by the alkyl polarizability effect index (PEI), where compounds with alkyl of higher PEI have lower ν em . Second, the λ em of salen-type Schiff bases can be quantified by an equation of the seven parameters, PEI, σ(X) ─OH , σ(X) ─CH═N , σ ex CC X ð Þ ─OH , σ ex CC X ð Þ ─CH═N , Δσ 2 p and Δσ 2 m , form where the stability and predictive ability of the obtained equation was confirmed by leave-one-out cross validation. Lastly, it was observed that the influence on the λ em of substituent X attached to the aromatic ring is related to its position relative to OH or CH═N groups as reference, whose Hammett constants (σ(X) ─OH , σ(X) ─CH═N ) and the excited-state substituent constants (σ ex CC X ð Þ ─OH , σ ex CC X ð Þ ─CH═N ) of the substituents X with varying locating methods have different effects on the λ em ;and that there is a "homoring competition effect" of substituent.

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Preparation, regulation and biological application of a Schiff base fluorescence probe

Cited by 11 publications

References 23 publications

Selective and Sensitive Two New Macroacyclic Schiff base Fluorescent Turn‐Off Receptors for Fe³⁺, DFT Calculation and Their Antibacterial Activity

Selective and Sensitive Two New Macroacyclic Schiff base Fluorescent Turn‐Off Receptors for Fe³⁺, DFT Calculation and Their Antibacterial Activity

A highly selective and sensitive turn‐on fluorescent probe for the detection of Al³⁺ and its bioimaging

Influences of polarizability effect of alkyl group and homoring competition effect of substituents on the fluorescence emission spectra of salen‐type Schiff bases

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Preparation, regulation and biological application of a Schiff base fluorescence probe

Cited by 11 publications

References 23 publications

Selective and Sensitive Two New Macroacyclic Schiff base Fluorescent Turn‐Off Receptors for Fe3+, DFT Calculation and Their Antibacterial Activity

Selective and Sensitive Two New Macroacyclic Schiff base Fluorescent Turn‐Off Receptors for Fe3+, DFT Calculation and Their Antibacterial Activity

A highly selective and sensitive turn‐on fluorescent probe for the detection of Al3+ and its bioimaging

Influences of polarizability effect of alkyl group and homoring competition effect of substituents on the fluorescence emission spectra of salen‐type Schiff bases

Contact Info

Product

Resources

About

Selective and Sensitive Two New Macroacyclic Schiff base Fluorescent Turn‐Off Receptors for Fe³⁺, DFT Calculation and Their Antibacterial Activity

Selective and Sensitive Two New Macroacyclic Schiff base Fluorescent Turn‐Off Receptors for Fe³⁺, DFT Calculation and Their Antibacterial Activity

A highly selective and sensitive turn‐on fluorescent probe for the detection of Al³⁺ and its bioimaging