The “Off-On” Fluorescence Detection of Alkaline Earth Metal Ions by Using 1-Naphthylacetanilide Derivatives: New Cation Sensors Based on Oligo-ethylene Oxides Connecting 1-Naphthylacetanilide at Its Terminals

Morozumi, Tatsuya; Hama, Hiroya; Nakamura, Hiroshi

doi:10.2116/analsci.22.659

Cited by 8 publications

(3 citation statements)

References 12 publications

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“…[20][21][22][23][24][25] In earlier papers, we described several fluoroionophores based on linear polyethers having fluorescence molecules at their terminals. [20][21][22][23][26][27][28] These ionophores gave fluorescence behavior from weak to strong emission upon metal ion complexation. Recently, we also reported a new mode of PET in fluorophore connecting N-phenylamide derivatives and its applications for chemosensors based on crown ether.…”

Section: Introductionmentioning

confidence: 99%

New “Off-On” Responsible Fluoroionophores for Alkaline Earth Metal Ions Based on Benzo-15-crown-5 Bearing 9-Phenanthreneacetamide

et al. 2009

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The photochemical behaviors of a series of 9-phenanthreneacetamide (PA) derivatives were investigated using UV, fluorescence, and 1 H-NMR spectroscopy in acetonitrile solutions. To apply the electron transfer (ET) action of PA as a detecting moiety of chemosensors, 4¢-(9-phenanthreneacetamido)-benzo-15-crown-5 (1) and 3¢-methyl-4¢-(9-phenanthreneacetamido)-benzo-15-crown-5 (2) were synthesized. After metal ion complex formation, the fluorescence intensity increased with increased concentration of the guest alkaline earth metal ions. The photochemical responses of the fluorescence intensity, as defined by the fluorescence intensity ratio (Imax/I0) between free and complex of 1 for Ca 2+ , was determined to be 4.76. However, the addition of guest ions in a solution of 2 greatly enhanced the fluorescence intensity of 2. The Imax/I0 of 2 was 16.6 for Ca 2+. The efficiency of ET of PA can be tuned by adding an electron-donating group onto a suitable position; fluorescent 2 was able to read out metal ions as an "Off-On" fluorescence signal.

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Section: Introductionmentioning

confidence: 99%

New “Off-On” Responsible Fluoroionophores for Alkaline Earth Metal Ions Based on Benzo-15-crown-5 Bearing 9-Phenanthreneacetamide

et al. 2009

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“…Subsequently, a few other examples of such donor-acceptor containing oligomers have been described in the literature. 10 The use of oligooxyethylene (OE-n) segment as linkers has also been extensively studied in the context of sensors [11][12][13] and more recently with regard to foldamers. [14][15][16][17] In these systems, the complexation of the OE segment by a metal-ion leads to either a spectroscopic modulation (sensing) or it leads to the formation of a specific folded conformer.…”

Section: Introductionmentioning

confidence: 99%

Understanding the folding process of synthetic polymers by small-molecule folding agents

Ramkumar

Ramakrishnan

2008

J Chem Sci

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Two acceptor containing polyimides PDI and NDI carrying pyromellitic diimide units and 1,4,5,8-naphthalene tetracarboxy diimide units, respectively, along with hexa(oxyethylene) (EO6) segments as linkers, were prepared from the corresponding dianhydrides and diamines. These polyimides were made to fold by interaction with specifically designed folding agents containing a dialkoxynaphthalene (DAN) donor linked to a carboxylic acid group. The alkali-metal counter-ion of the donor carboxylic acid upon complexation with the EO6 segment brings the DAN unit in the right location to induce a charge-transfer complex formation with acceptor units in the polymer backbone. This two-point interaction between the folding agent and the polymer backbone leads to a folding of the polymer chain, which was readily monitored by NMR titrations. The effect of various parameters, such as structures of the folding agent and polymer, and the solvent composition, on the folding propensities of the polymer was studied.

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“…Their photochemical action of complexation suggested that the most likely relaxation pathway was twisted intramolecular charge transfer (TICT). To extend these investigations, we synthesized novel chemosensors based on benzo-crown ether 4 and linear polyether 5 possessing N-phenyl-1-naphthalenelacetamide. These sensors indicated that the binding of alkaline earth metal ions is signaled by a switching "on" of the naphthalene fluorescence.…”

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confidence: 99%

Anomalous Fluorescent Responses of 9-Fluorenecarboxamide Derivatives Possessing Benzo-15-crown-5

2007

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The importance of electron-transfer reactions has attracted many researchers to investigate the fundamental steps of the processes. Especially, many studies have been devoted to photo-induced electron transfer (PET) in electron donoracceptors linked by a covalent bond system. 1 In that context, we have reported photochemical behavior of a series of donoracceptor systems. Recently, we reported that some aromatic amide derivatives that have fluorescent active groups in the molecules showed quite weak emission. The presence of Nphenyl-amide groups caused the formation of charge separation at the excited state through electron transfer between fluorescence-active groups and a benzene ring via the amide bond. Using results of a previous study, new fluorescent ionophores based on an ethyleneoxy chain containing N-phenyl-9-anthracenecarboxamide 2 and N-phenyl-1-pyrenylcarboxamide 3 were synthesized and characterized. These fluoroionophores showed weak emission corresponding to their monomers in the absence of metal ions, although their alkaline earth metal ion complexes indicated strong emissions. Their photochemical action of complexation suggested that the most likely relaxation pathway was twisted intramolecular charge transfer (TICT). To extend these investigations, we synthesized novel chemosensors based on benzo-crown ether 4 and linear polyether 5 possessing N-phenyl-1-naphthalenelacetamide. These sensors indicated that the binding of alkaline earth metal ions is signaled by a switching "on" of the naphthalene fluorescence. Fluorescence spectroscopic data suggest that their quenching process was intermolecular charge transfer involving a TICT character. These results might be construed to mean that TICT has occurred not only through the amide bond but also over the CH2 group. The concept of TICT usually emphasizes the torsion of a single bond, although the CT action of these cases was obtained over the two bonds (amide and CH2 group). The charge-transfer behavior of N-phenyl-1-naphthaleneacetamide was unique.We used 9-fluorenecarboxamide as a comparison to confirm that this CT action is peculiar to naphthalene. Fluorene has a similar UV absorption band to that of naphthalene, in addition to a unique bridge carbon out of the conjugation constructed by the biphenyl moiety. A similar UV absorption spectrum would probably use the same excited-state. The nine-positioned carbon should provide evidence for considering of the effects of the donor-acceptor distance. Fluorene is also a promising material for organic light-emitting devices because of its good chemical stability and high photoluminescence quantum efficiency, both in solution and in the solid state. 6 In addition, in the biochemical field, it has been used as "molecular beacons" for detecting nucleic acid hybridization. 7,8 Despite their advantages, applications for analytical use and signaling purposes using fluorene are rather limited.In this communication, using fluorescence, UV, and NMR spectrometries, we describe the photochemical behaviors A new fluore...

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The “Off-On” Fluorescence Detection of Alkaline Earth Metal Ions by Using 1-Naphthylacetanilide Derivatives: New Cation Sensors Based on Oligo-ethylene Oxides Connecting 1-Naphthylacetanilide at Its Terminals

Cited by 8 publications

References 12 publications

New “Off-On” Responsible Fluoroionophores for Alkaline Earth Metal Ions Based on Benzo-15-crown-5 Bearing 9-Phenanthreneacetamide

New “Off-On” Responsible Fluoroionophores for Alkaline Earth Metal Ions Based on Benzo-15-crown-5 Bearing 9-Phenanthreneacetamide

Understanding the folding process of synthetic polymers by small-molecule folding agents

Anomalous Fluorescent Responses of 9-Fluorenecarboxamide Derivatives Possessing Benzo-15-crown-5

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