Fluorescence quenching of versatile fluorescent probes based on strongly electron-donating distyrylbenzenes responsive to aromatic chlorinated and nitro compounds, boronic acid and Ca2+

Abstract

The fluorescence quenching behavior of two distyrylbenzenes (DSBs) newly prepared bearing strongly electron-donating groups was investigated. Several chlorinated and nitro compounds quench the fluorescence of both DSBs with various efficiencies depending on the electron-withdrawing properties; the strongly electron-withdrawing compound, such as 2,4,5-trichlorophenol and 2,4-dinitrofluorobenzene, effectively diminish the fluorescence intensities of the DSBs. Since the fluorescence quenching constants and the reduction potentials of the quenchers are linearly related, these quenching phenomena are attributed to the photo-induced electron transfer (PET) process. The fluorescence quenching was also detected in the interaction between the azacrown DSB and phenylboronic acid, while the fluorescence recovers by adding triethylamine. On the other hand, the azacrown DSB selectively interacts with Ca 2+ to decrease its fluorescence intensity, but the DSB with the dimethylamino groups did not. These results suggest a potential use of these types of compounds as sensors for strongly electron-withdrawing substances and a suitable metal cation.

Design and Applications of Small Molecular Probes for Calcium Detection

“…[53] Motoyoshiya et al reported distyrylbenzenes based derivative 40 linked with an electron donating group for the binding of Ca 2 + ions ( Figure 13). [54] In THF, 40 showeds trong emission at 485 nm (F = 0.51). However, upon incremental addition of Ca 2 + ions into the solution of receptor 40 resulted in the decrease of fluorescencei ntensity.T his was ascribed to the binding of Ca 2 + ions with azacrown ether moiety.I na ddition to these examples, dinuclearc alcium complexes of oxa-azamacrocyclic receptors have also been reported.…”

“…Motoyoshiya et al. reported distyrylbenzenes based derivative 40 linked with an electron donating group for the binding of Ca 2+ ions (Figure ) . In THF, 40 showed strong emission at 485 nm ( Φ =0.51).…”

Real‐Time Probe for the Efficient Sensing of Inorganic Fluoride and Copper Ions in Aqueous Media

“…This color enhancement could be attributed to “through bond energy transfer” (TBET) phenomenon . The absence of fluorescent property of probe P3 was attributed to the presence of highly electron withdrawing nitro groups which will quench the fluorescence of probe P3 …”

Novel Linear Bis-Crown Receptors with Cross-Conjugated and Conjugated Central Cores

“…[60][61][62] These and a number of other properties have recently made 1,4-distyrylbenzenes attractive objects for the creation of photoactive materials: organic light-emitting diodes, materials for solar batteries, nonlinear optical materials and chemical sensors. [63][64][65][66][67][68] The first representative of bis-crown 1,4-distyrylbenzenes, bis(15-crown-5)-1,4-distyrylbenzene (3i), was obtained earlier, [69] using the Wittig-Horner reaction by condensation of bisphosphonate 5 with 4'-formylbenzo-15-crown-5-ester 6i under the action of 85 % aqueous KOH solution when refluxing in benzene with a yield of 53 %. One of the drawbacks of this approach, discovered when reproducing the procedure, was the need for additional purification of 3i by recrystallization from dioxane, which resulted in a significant decrease in yield.…”