Fluorescence PET (photo-induced electron transfer) sensors for water based on anthracene–boronic acid ester

Ooyama, Yousuke; Matsugasako, Ai; Oka, Kazuyuki; Nagano, Tomoya; Sumomogi, Minako; Komaguchi, Kenji; Imae, Ichiro; Harima, Yutaka

doi:10.1039/c1cc10470e

Cited by 122 publications

(63 citation statements)

References 25 publications

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“…These materials have found great utility in sensing humidity [1][2][3][4][5][6][7][8][9][10][11][12] and measuring the water contents of organic solvents. [13][14][15][16][17][18] Designs of hydrochromic humidity sensors can be based on conjugated organic molecules that undergo color changes associated with polarity changes caused by exposure to water. [ 1,2 ] Certain periodically ordered polymer fi lms, which have refl ectance wavelengths that the interchain distance in this polymer leads to partial distortion of the arrayed p-orbitals and an associated change in the wavelength maximum for visible light absorption.…”

Section: Introductionmentioning

confidence: 99%

“…[3][4][5][6] Hydrochromic substances bearing amino-coupled fl uorophores also have been employed to determine the presence of water in organic solvents. [ 13,14 ] Sensors of this type emit only weak fl uorescence owing to the occurrence of facile quenching caused by photoinduced electron transfer (PET) from the amine moiety to the fl uorophore. However, in these systems blocking PET quenching by the formation of ammonium salt containing zwitterions when water is present in organic solvents results in the generation of strong fl uorescence.…”

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confidence: 99%

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Inkjet‐Printable Amphiphilic Polydiacetylene Precursor for Hydrochromic Imaging on Paper

Park

Jeong

Seo

et al. 2015

Adv Funct Materials

119

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Hydrochromic materials find great utility in a wide range of applications including humidity sensing and measuring the water contents of organic solvents, as well as substrates for rewritable paper and human sweat pore mapping. Herein, an inkjet printable diacetylene (DA) is described that can be transformed by UV irradiation to a hydrochromic‐conjugated polymer on conventional paper. Specifically, an amphiphilic DA that contains an imidazolium ion head‐group is found to be compatible with a common office inkjet printer. Various computer‐designed images are printed on paper using this substance. UV irradiation of the printed images results in the generation of blue‐colored images associated with formation of a polydiacetylene (PDA). The resolutions of the images are almost identical to those generated using a conventional black ink. Importantly, the printed images undergo a blue‐to‐red color change upon exposure to water and the hydrochromism is found to be temperature dependent. The facile color change that occurs near body temperatures enables use of the hydrochromic PDA‐coated paper for rapid and precise mapping of human sweat pores from fingers, palms, and feet.

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Section: Introductionmentioning

confidence: 99%

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confidence: 99%

Inkjet‐Printable Amphiphilic Polydiacetylene Precursor for Hydrochromic Imaging on Paper

Park

Jeong

Seo

et al. 2015

Adv Funct Materials

119

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“…The results demonstrated that the fluorescence behavior of Mg-dpa-HC changed noticeably in the presence of a small amount of water. Therefore, Mg-dpa-HC shows potential for use as a highly sensitive sensor for the quantitative measurement of a trace amount of water in organic solvents 23 and real time imaging sensor for Mg 2+ in the cell membrane.…”

Section: +mentioning

confidence: 99%

Solvent Effect on the Fluorescence Response of Hydroxycoumarin Bearing a Dipicolylamine Binding Site to Metal Ions

et al. 2014

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The fluorescence behavior of a probe dpa-HC, which has a coumarin derivative that acts as a fluorophore and a dipicolylamine (DPA) unit that functions as a metal ion-recognition site, was investigated with various metal ions in aqueous and several non-aqueous solvents. In aqueous solution, the fluorescence of dpa-HC was enhanced by Zn 2+ and Cd 2+ , but was quenched by other metal ions. On the other hand, in an acetonitrile solution, only Mg 2+ enhanced the fluorescence, and the addition of a small amount of water quenched this fluorescence. This dramatic selectivity change is explained by stabilization of a metal-dpa-HC complex due to acetonitrile coordination and ON-OFF switching of the intramolecular photoinduced electron transfer (PET) from the nitrogen lone pair of DPA to the coumarin derivative. Scheme 1 Synthesis of 8-(2,2′-dipicolylaminomethyl)-7-hydroxycoumarin (dpa-HC). Keywords

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“…7,8 Recently, numerous new types of boronic acid sensors have been fabricated to detect blood glucose concentrations, [9][10][11][12][13] ionic compounds, [14][15][16][17] traces of water in solvents, 18,19 hydrogen peroxide (H 2 O 2 ), [20][21][22] catecholamines, 23 as well as using boronic acids as biochemical tools for various applications, including tumor cell imaging, 24,25 enzyme inhibitors 26 and cell delivery systems. 27 Therefore, the boron-based uorescent sensor is still hot in today's research.…”

Section: 5mentioning

confidence: 99%

Recent development of boronic acid-based fluorescent sensors

et al. 2018

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As Lewis acids, boronic acids can bind with 1,2-or 1,3-diols in aqueous solution reversibly and covalently to form five or six cyclic esters, thus resulting in significant fluorescence changes. Based on this phenomenon, boronic acid compounds have been well developed as sensors to recognize carbohydrates or other substances. Several reviews in this area have been reported before, however, novel boronic acid-based fluorescent sensors have emerged in large numbers in recent years. This paper reviews new boronbased sensors from the last five years that can detect carbohydrates such as glucose, ribose and sialyl Lewis A/X, and other substances including catecholamines, reactive oxygen species, and ionic compounds. And emerging electrochemically related fluorescent sensors and functionalized boronic acid as new materials including nanoparticles, smart polymer gels, and quantum dots were also involved.By summarizing and discussing these newly developed sensors, we expect new inspiration in the design of boronic acid-based fluorescent sensors.

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Fluorescence PET (photo-induced electron transfer) sensors for water based on anthracene–boronic acid ester

Abstract: Anthracene-boronic acid ester as a new class of fluorescence PET sensors for detection of a trace amount of water in organic solvents has been designed and developed.

Cited by 122 publications

References 25 publications

Inkjet‐Printable Amphiphilic Polydiacetylene Precursor for Hydrochromic Imaging on Paper

Inkjet‐Printable Amphiphilic Polydiacetylene Precursor for Hydrochromic Imaging on Paper

Solvent Effect on the Fluorescence Response of Hydroxycoumarin Bearing a Dipicolylamine Binding Site to Metal Ions

Recent development of boronic acid-based fluorescent sensors

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