Effects of Cyclodextrins on Intramolecular Photoinduced Electron Transfer in a Boronic Acid Fluorophore

Hiroya, Kou; Tanoue, Daichi; Shimaoka, Hiroaki; Katano, Kohei; Hashimoto, Takeshi; Kunugita, Hideyuki; Nanbu, Shinkoh; Hayashita, Takashi; Ema, Kazuhiro

doi:10.2116/analsci.30.643

Cited by 10 publications

(9 citation statements)

References 26 publications

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“…Boronic acids have been widely used as sugar receptors for developing chemical sugar sensors; [4][5][6][7] borinates have been neglected from this perspective due to the difficulty in designing a system that can obtain a signal change through an ester formation between a borinate and sugar. Although there are some strategies for boronic acidbased sensors such as internal charge transfer (ICT), [7][8][9] photoinduced electron transfer (PET), 10,11 fluorescence resonance energy transfer, 12 excimer 13 and exciplex, 14 these systems have never been utilised to develop a sugar sensor including a borinate.…”

Section: Introductionmentioning

confidence: 99%

A red fluorophore comprising a borinate-containing xanthene analogue as a polyol sensor

et al. 2016

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A xanthene derivative containing a borinate moiety emitted red fluorescence with a high quantum yield. The interaction between the borinate and a sugar molecule induced a fluorescence change based on the change in the HOMO-LUMO gap. The response was pH-resistant in a wide range. In addition, catechol quenched through photoinduced electron transfer. The red fluorescence and polyol binding ability of dyes will pave the way for new biological applications of chemical sensors.

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Section: Introductionmentioning

confidence: 99%

A red fluorophore comprising a borinate-containing xanthene analogue as a polyol sensor

et al. 2016

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“…Not only the intramolecular PET processes were suppressed by macrocycles, but also the intermolecular ones. For example, b-CD-retarded PET between dimethyl aniline (donor) and different 7-amino coumarin derivatives (acceptor) in DMF solution was confirmed by Chakraborty et al (15) upon the binding of the acceptor molecules to the host cavity. Excited state electron/ proton transfer from lucifer yellow and/or chlorin P6 to methyl viologen in b-CD, leading to PET suppression, was studied (18).…”

Section: Encapsulation Of Acceptor Alonementioning

confidence: 84%

“…Suppression of PET through a supramolecular approach has been justified by many researchers through the encapsulation of the acceptor unit of a PET‐enabled dyad (13,14,16,17). For instance, Graham et al .…”

Section: Mechanisms To Disrupt Pet Quenching By a Supramolecular Appr...mentioning

confidence: 99%

Photoinduced Electron Transfer in Encapsulated Heterocycles by Cavitands

Bojesomo

Saleh

2021

Photochem & Photobiology

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Host−guest complexation of small heterocyclic (guest) and macrocyclic cavitands (hosts) organic molecules is still to date a very popular, inexpensive approach that bypasses the burdens of conventional covalent synthesis. Understanding the selection criteria of these chemicals is crucial to the design and potential applications of their supramolecular assemblies. This review surveys examples within the last 15 years (2005–2020) of supramolecular complexes in which the interacting photoinduced electron transfer (PET)‐based chromophore and quencher fragments are commonly used in the market with reported CAS numbers. It appears from this survey that the supramolecular effects can be directed to specifically disrupt PET when the nonemissive macrocycles separately encapsulate the fluorescent acceptor or donor molecules, among other specific factors, such as when inducing conformational changes or pKa shift of the donor. On the contrary, synergetic encapsulation of both donor and acceptor molecules, formation of ternary self‐assembly at the rim or encapsulation of one component while grafting the other onto the macrocycle, among other specific factors such as the modulation of the excited‐state structure of donor, will lead to the enhancement of PET process. In the event the donor or acceptor molecules have multitopic structures, the PET process can repeatedly be switched on and off. It is generally concluded that understanding the criteria for the combination of these available products for the purpose of manipulating their PET efficiency should pave the way for the facile alternative generation of new noncovalently bonded host−guest supramolecular assemblies with a more specific design tailored for more advanced, diverse and economic applications such as chemical sensing, molecular gates, drug delivery and biolabeling.

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“…1, soyasaponin Bb has one carboxyl group and two cis-diol groups, which react with borate anion to form a negatively charged ester. [14][15][16] In the borax solution, the borate anion would be formed according to the following reaction: B4O7 2-+ 7H2O = 2B(OH)4 -+ 2B(OH)3.…”

Section: Ce Of Standard Materials Of Soyasaponins Bb and Bamentioning

confidence: 99%

Simple and Rapid Separation of Soyasaponin Bb from a Soy Extract

et al. 2015

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Soyasaponins Ba and Bb were obtained from Funakoshi Co., Ltd., and were used as standard materials. A crude soyasaponin was purchased from Fuji Oil Co., Ltd., and used as the starting material. Other chemicals were of reagent grade, and were used 2015 © The Japan Society for Analytical Chemistry † To whom correspondence should be addressed. A simple method to separate soyasaponin Bb from a soy extract is presented. This method is based on the difference in the solubility of soyasaponin Bb and Ba and other components into 3:7 and 1:1 (v/v) acetone-water mixed solvents. The crude soyasaponin consisting of soyasaponins Aa, Ab, Ba, and Bb at the 10 wt% level and other components was examined as the soy extract. A 10 mg quantity of the crude soyasaponin was mixed with 1 mL of the 3:7 acetone-water containing 0.1 mol/L HCl, and the supernatant was removed to obtain a precipitate, which was found to contain mainly soyasaponins Bb and Ba. The precipitate was mixed with 0.4 mL of the 1:1 acetone-water containing 0.1 mol/L HCl; the supernatant was transferred, and was mixed with 0.6 mL of water to obtain a precipitate, which was found to contain mainly soyasaponin Bb. The yield was ca. 30%, which may be much higher than that by the conventional preparative chromatographic approach. The separation method is rapid and easy to carry out, and is useful for the preparation of a soyasaponin Bb sample.

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Effects of Cyclodextrins on Intramolecular Photoinduced Electron Transfer in a Boronic Acid Fluorophore

Cited by 10 publications

References 26 publications

A red fluorophore comprising a borinate-containing xanthene analogue as a polyol sensor

A red fluorophore comprising a borinate-containing xanthene analogue as a polyol sensor

Photoinduced Electron Transfer in Encapsulated Heterocycles by Cavitands

Simple and Rapid Separation of Soyasaponin Bb from a Soy Extract

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