Fluorescence ‘reading-out’ of the molecular-recognition process

Aoki, Izuo; Harada, Takaaki; Sakaki, Takeshi; Kawahara, Yohko; Shinkai, Seiji

doi:10.1039/c39920001341

Cited by 75 publications

(82 citation statements)

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“…Benzylic hydogen peak of pyrenemethylamine hydrochloride shifted to higher magnetic field ( Figure 5) and two doublets (4.70 ppm and 4.13 ppm) due to OCH 2 CO 2 shifted to lower field. These results imply that the two OCH 2 CO 2 groups act as acceptors for RNH 3 + protons. From the NMR titration study, the binding constant of pyrenemethylamine hydrochloride to nitrobenzene modified calixarene 1 calculated as 950 M −1 .…”

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confidence: 69%

“…The compound 3 was obtained in 60% yield. Refluxing the compound 3 in acidic condition gave the hexahomotrioxacalix [3]arene 4 in 50% yield. 7 In this condition only partial cone calixarene was obtained.…”

mentioning

confidence: 99%

“…A series of chromogenic calixarene derivatives has been synthesized which exhibit a change in their UV/ VIS or fluorescence spectra in the presence of metal ions or organic guest molecules. 1 Shinkai et al reported functionalized hexahomotrioxacalix [3]arenes and calix [4]arenes which could detect ammonium ions or metal ions by means of fluorescence change in the pyrene functionalized calixarenes. They made use of intramolecular excimer fluorescence change of pyrene 2 and disturbance of quenching efficiency between pyrene and nitrobenzene.…”

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confidence: 99%

“…They made use of intramolecular excimer fluorescence change of pyrene 2 and disturbance of quenching efficiency between pyrene and nitrobenzene. 3,4 As ammonium ions play important roles in both chemistry and biology, 5,6 we designed nitrobenzene modified calixarene 1 which can detect ammonium ions carrying fluorescence group. When ammonium ions with fluorescence group bind the calixarene 1, fluorescence of the ammonium ions would be effectively quenched and change of emission intensity would provide the information of ammonium ion binding events.…”

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confidence: 99%

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Nitrobenzene Functionalized Hexahomotrioxacalix[3]arene

2002

Bulletin of the Korean Chemical Society

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The synthesis and characterization of a nitrobenzene modified hexahomotrioxacalix[3]arene 1 are described. When calixarene 1 bound with ammonium ions carrying fluorescence group, the fluorescence of ammonium ions were effectively quenched and change of emission intensity provided the information of ammonium ion binding events to the calixarene 1.Keywords : Calixarene, Ammonium ion, Fluorescence.Calixarenes are homologous cyclic compounds which are synthesized by the condensation reactions between parasubstituted phenols and formaldehydes. They usually take bowl-shaped conformation which could bind guest molecules. They form complexes with various cations and organic molecules selectively. Therefore, their usability as host and sensor has been a matter of intensive investigations. For sensor applications, the generation of optical signal as a direct result of the complexation between host and guest is desirable. A series of chromogenic calixarene derivatives has been synthesized which exhibit a change in their UV/ VIS or fluorescence spectra in the presence of metal ions or organic guest molecules.1 Shinkai et al. reported functionalized hexahomotrioxacalix[3]arenes and calix [4]arenes which could detect ammonium ions or metal ions by means of fluorescence change in the pyrene functionalized calixarenes. They made use of intramolecular excimer fluorescence change of pyrene 2 and disturbance of quenching efficiency between pyrene and nitrobenzene.3,4 As ammonium ions play important roles in both chemistry and biology, 5,6 we designed nitrobenzene modified calixarene 1 which can detect ammonium ions carrying fluorescence group. When ammonium ions with fluorescence group bind the calixarene 1, fluorescence of the ammonium ions would be effectively quenched and change of emission intensity would provide the information of ammonium ion binding events.Preparation of the calixarene 1 is summarized in Figure 1. The synthesis started from the reaction between p-tert-butylphenol 2 and formaldehyde in basic condition. The compound 3 was obtained in 60% yield. Refluxing the compound 3 in acidic condition gave the hexahomotrioxacalix[3]arene 4 in 50% yield. 7 In this condition only partial cone calixarene was obtained. This was followed by substitution reaction with the compound 5 to give the final compound 1 in 40% yield. 8The fluorescence change of ammonium ions with fluorescence group was monitored in the mixture of acetonitrile and chloroform (99 : 1). The fluorescence intensity of 3 µM solution of ammonium ions changed remarkably as the concentration of nitrobenzene modified calixarene 1 was increased (Figure 2). In case of pyrenemethylamine hydrochloride, the excitation wavelength was 343 nm. In Figure 3, a Benesi-Hildebrand plot 9 of the mixture of pyrenemethylamine hydrochloride and nitrobenzene modified calixarene 1 by use of change in the 378 nm fluorescence intensity is shown. Equilibrium constant K was calculated from the slope. Similar measurements for several amines with fluorescence probe were carried out and t...

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confidence: 69%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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Nitrobenzene Functionalized Hexahomotrioxacalix[3]arene

2002

Bulletin of the Korean Chemical Society

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“…[7][8][9][10][11][12][13][14][15][16][17] Several groups have recently reported the fluorometric detection of Na + using the calix [4]arene derivatives bearing pyrenyl groups. On these calix [4]arene-based fluorescence sensors, Na + complexation can be monitored by intramolecular pyrene excimer emission and extinction, 18,19 disruption of the intramolecular photoinduced electron transfer from the pyrene to nitrobenzene, 20 and induction of the intramolecular fluorescence energy transfer from the pyrene to anthracene. Perylene exhibits a more intense fluorescence than pyrene, and the fluorescence emission band of perylene significantly overlaps with the absorption band of pyrene.…”

Section: Introductionmentioning

confidence: 99%

Effective fluorescent sensing of Na+ ion by calix[4]arene bearing pyrene and perylene based on energy transfer

Nishimura¹,

Takemura²,

Arai³

2007

Arkivoc

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A new calix [4]arene having pyrene and perylene moieties has been synthesized as a Na + detectable fluorescent ionophore. When excited at the pyrene moiety (342 nm) of the ionophore, a strong fluorescence emission of the perylene moiety (535 nm) was observed due to energy transfer from the pyrene to perylene. By addition of Na + at a low concentration in the range of 2.5-10 µM, the fluorescence was remarkably quenched. In contrast to the fluorescent behavior by the ionophore having pyrene and perylene moieties, the excimer emission of a calix[4]arene derivative having two pyrene moieties decreased by the addition of Na + with a concentration in the range of 50-200 µM.

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The Effects of Avidin on Inclusion Phenomena and Fluorescent Properties of Biotin-Appended Dansyl-Modifiedβ-Cyclodextrin

1999

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Two biotin-appended dansylmodified cyclodextrins 3 and 4 were prepared to examine the effects of avidin binding on guest-inclusion phenomena and fluorescence properties of cyclodextrin derivatives. The fluorescence intensities of hosts 3 and 4 are more than three times larger in the presence of avidin than those in the absence of avidin. The fluorescence lifetime measurements indicate that the dansyl moiety is not exposed to bulk water in the presence of avidin. The longer lifetime component, which newly appears in the presence of avidin, is likely to be that of the dansyl moiety located in the hydrophobic region of avidin. The addition of bile acids such as hyodeoxycholic acid resulted in decreases in the fluorescence intensities of 3 and 4 in accordance to the extrusion of the dansyl moiety from the hydrophobic cyclodextrin cavity to bulk water. Similar guest-induced decreases in the fluorescence intensity were observed for 3 in the presence of avidin, but under the same conditions the decreases are smaller for 4. On the other hand, the binding constants of 3 and 4 became larger in the presence of avidin. All these results demonstrate that avidin perturbs the inclusion phenomena and fluorescence properties of 3 and 4 by providing a hydrophobic environment around the host cavity.

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Fluorescence ‘reading-out’ of the molecular-recognition process

Abstract: The binding of guest molecules sensitively influences the fluorescent behaviour of barbiturate-incorporated fluorescent pyrenes, making it possible to 'read-out' the molecular-recognition process by a fluorescence spectroscopic technique.

Cited by 75 publications

References 10 publications

Nitrobenzene Functionalized Hexahomotrioxacalix[3]arene

Nitrobenzene Functionalized Hexahomotrioxacalix[3]arene

Effective fluorescent sensing of Na+ ion by calix[4]arene bearing pyrene and perylene based on energy transfer

The Effects of Avidin on Inclusion Phenomena and Fluorescent Properties of Biotin-Appended Dansyl-Modifiedβ-Cyclodextrin

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