Design of bisquinolinyl malonamides as Zn2+ ion-selective fluoroionophores based on the substituent effect

Moriuchi‐Kawakami, Takayo; Kawata, Kenji; Nakamura, Shotaro; Koyama, Yoshiaki; Shibutani, Yasuhiko

doi:10.1016/j.tet.2014.11.016

Cited by 9 publications

(3 citation statements)

References 35 publications

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“…In 2014, Moriuchi-Kawakami and co-workers synthesised a range of malonamides possessing quinoline moities used as fluoroionphores for zinc (Zn 2 + ) sensing applications (Scheme 12). [29] As the final step in their stepwise synthesis, malonyl chlorides (bearing methylene substituents) were reacted with 8-aminoquinoline to access four malonamide Scheme 10. Synthesis of malonamide derivatives from malonyl chlorides.…”

Section: Synthesis Of Malonamides From Malonyl Chlorides/acid Chloridesmentioning

confidence: 99%

“…In 2014, Moriuchi‐Kawakami and co‐workers synthesised a range of malonamides possessing quinoline moities used as fluoroionphores for zinc (Zn 2+ ) sensing applications (Scheme 12). [29] As the final step in their stepwise synthesis, malonyl chlorides (bearing methylene substituents) were reacted with 8‐aminoquinoline to access four malonamide derivatives in yields up to 46 %. The authors recommended the use of either benzene, which presents significant risk of health hazard on exposure, or toluene, documented to have serious negative air impact, as solvent.…”

Section: Synthesis Of Malonamidesmentioning

confidence: 99%

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Syntheses and Applications of Malonamide Derivatives – A Minireview

Aderibigbe

Day

2020

ChemistrySelect

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Malonamide derivatives are an important class of organic compounds utilized in an array of applications. As such, numerous research efforts have focused on ways to synthesize and decorate these molecules. This minireview is separated into sections focusing on syntheses of malonamide derivatives from key starting materials. Throughout this report, critical analysis of the routes to and applications of malonamide derivatives are documented, highlighting the adaptability across scientific fields.

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Section: Synthesis Of Malonamides From Malonyl Chlorides/acid Chloridesmentioning

confidence: 99%

Section: Synthesis Of Malonamidesmentioning

confidence: 99%

Syntheses and Applications of Malonamide Derivatives – A Minireview

Aderibigbe

Day

2020

ChemistrySelect

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“…In our previous studies, it was demonstrated that sandwich-type ion recognition compounds indicate excellent ion selectivity and that malonate is an excellent spacer for such compounds [ 48 , 49 , 50 ]. The substituents introduced into the C2-position of the malonate spacers affect the dihedral angles between the two ion recognition moieties, although the introduced substituents are spatially distant from the moieties [ 48 ]. In this study, we have designed and synthesized a new malonate possessing two pyrene moieties as a fluoroionophore.…”

Section: Introductionmentioning

confidence: 99%

Bis(1-pyrenylmethyl)-2-benzyl-2-methyl-malonate as a Cu2+ Ion-Selective Fluoroionophore

et al. 2017

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A new malonate possessing two pyrene moieties was synthesized as a fluoroionophore, and its structure and fluorescence spectroscopic properties were investigated. When excited at 344 nm in acetonitrile/chloroform (9:1, v/v), the synthesized bispyrenyl malonate has the fluorescence of intramolecular excimer (λem = 467 nm) emissions and not a pyrene monomer emission (λem = 394 nm). A large absolute fluorescence quantum yield was obtained in the solid state (ΦPL = 0.65) rather than in solution (ΦPL = 0.13). X-ray crystallography analysis clarified the molecular structure and alignment of the bispyrenyl malonate in the crystal phase, elucidating its fluorescence spectroscopic properties. Such analysis also suggests there are intramolecular C–H···π interactions and intermolecular π···π interactions between the pyrenyl rings. Interestingly, the synthesized bispyrenyl malonate exhibits excellent fluorescence sensing for the Cu2+ ion. Remarkable fluorescence intensity enhancement was only observed with the addition of the Cu2+ ion.

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Synthesis of Two Coumarin-Derived Schiff Bases and Investigation of theirs Selectivity for Zn2+

Fan¹

2017

J Fluoresc

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Design of bisquinolinyl malonamides as Zn2+ ion-selective fluoroionophores based on the substituent effect

Cited by 9 publications

References 35 publications

Syntheses and Applications of Malonamide Derivatives – A Minireview

Syntheses and Applications of Malonamide Derivatives – A Minireview

Bis(1-pyrenylmethyl)-2-benzyl-2-methyl-malonate as a Cu2+ Ion-Selective Fluoroionophore

Synthesis of Two Coumarin-Derived Schiff Bases and Investigation of theirs Selectivity for Zn2+

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