Molecular design, characterization, and application of multi-information dyes for multi-dimensional optical chemical sensing. Molecular design concepts of the dyes and their fundamental spectral characteristics

Hideaki Hisamoto, Hajime Tohma, Toshiki Yamada, Ki Ichiro Yamauchi, Dwi Siswanta, Naoki Yoshioka, Koji Suzuki

Research output: Contribution to journalArticle

57 Citations (Scopus)

Abstract

The molecular design of multi-functional dyes, called 'multi-information dyes' (MIDs), and their application to several methods of optical chemical sensing were proposed. The concepts for the molecular design of the dyes were as follows: (1) the introduction of multiple (both positive and negative) charges on both ends of the large conjugated π-electron system of the dye molecule, so that the dye interacts with many chemical species or environments; (2) the introduction of different substitution (electron-donating or electron-accepting) groups in the conjugated π-electron system of the dye molecule, so that the dye has a different pK(a) and solvatochromic property; and (3) the introduction of an immobilization site in the dye molecule, so that the dye can be easily prepared as a sensing probe.Based on these concepts, sixteen kinds of dyes were synthesized, all being of the merocyanine type. The basic color-change characteristics of the MIDs were evaluated with a homogeneous system and a solvent extraction two-phase system. Some of these dyes (e.g., KD-M5) offered two-dimensional sensing information for sensing the water content in organic solvents, in which the absorbance maximum wavelength (λ(max)) shift and absorbance change were both utilized as the detecting signals.From these results, the MIDs developed in this study have several possibilities for analytical applications in optical chemical sensing such as pH sensing, ion sensing, neutral molecule sensing, and water content-sensing in organic solvents. Copyright (C) 1998 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)271-289
Number of pages19
JournalAnalytica Chimica Acta
Volume373
Issue number2-3
DOIs
Publication statusPublished - 1998 Nov 11

Fingerprint

dye
Coloring Agents
Electrons
electron
Molecules
absorbance
chemical
Organic solvents
Water content
water content
Water
Solvent extraction
Immobilization
immobilization
substitution
Substitution reactions
Color
probe
Ions
wavelength

Keywords

  • Alcohol sensor
  • Functional dye
  • Ion sensor
  • Optical sensor
  • Optode
  • pH sensor
  • Solvatochromism
  • Water-content sensor

ASJC Scopus subject areas

  • Biochemistry
  • Analytical Chemistry
  • Spectroscopy
  • Environmental Chemistry

Cite this

Molecular design, characterization, and application of multi-information dyes for multi-dimensional optical chemical sensing. Molecular design concepts of the dyes and their fundamental spectral characteristics. / Hisamoto, Hideaki; Tohma, Hajime; Yamada, Toshiki; Yamauchi, Ki Ichiro; Siswanta, Dwi; Yoshioka, Naoki; Suzuki, Koji.

In: Analytica Chimica Acta, Vol. 373, No. 2-3, 11.11.1998, p. 271-289.

Research output: Contribution to journalArticle

@article{0b090dcffeab4d7b8a24939b23a58f03,
title = "Molecular design, characterization, and application of multi-information dyes for multi-dimensional optical chemical sensing. Molecular design concepts of the dyes and their fundamental spectral characteristics",
abstract = "The molecular design of multi-functional dyes, called 'multi-information dyes' (MIDs), and their application to several methods of optical chemical sensing were proposed. The concepts for the molecular design of the dyes were as follows: (1) the introduction of multiple (both positive and negative) charges on both ends of the large conjugated π-electron system of the dye molecule, so that the dye interacts with many chemical species or environments; (2) the introduction of different substitution (electron-donating or electron-accepting) groups in the conjugated π-electron system of the dye molecule, so that the dye has a different pK(a) and solvatochromic property; and (3) the introduction of an immobilization site in the dye molecule, so that the dye can be easily prepared as a sensing probe.Based on these concepts, sixteen kinds of dyes were synthesized, all being of the merocyanine type. The basic color-change characteristics of the MIDs were evaluated with a homogeneous system and a solvent extraction two-phase system. Some of these dyes (e.g., KD-M5) offered two-dimensional sensing information for sensing the water content in organic solvents, in which the absorbance maximum wavelength (λ(max)) shift and absorbance change were both utilized as the detecting signals.From these results, the MIDs developed in this study have several possibilities for analytical applications in optical chemical sensing such as pH sensing, ion sensing, neutral molecule sensing, and water content-sensing in organic solvents. Copyright (C) 1998 Elsevier Science B.V.",
keywords = "Alcohol sensor, Functional dye, Ion sensor, Optical sensor, Optode, pH sensor, Solvatochromism, Water-content sensor",
author = "Hideaki Hisamoto and Hajime Tohma and Toshiki Yamada and Yamauchi, {Ki Ichiro} and Dwi Siswanta and Naoki Yoshioka and Koji Suzuki",
year = "1998",
month = "11",
day = "11",
doi = "10.1016/S0003-2670(98)00421-8",
language = "English",
volume = "373",
pages = "271--289",
journal = "Analytica Chimica Acta",
issn = "0003-2670",
publisher = "Elsevier",
number = "2-3",

}

TY - JOUR

T1 - Molecular design, characterization, and application of multi-information dyes for multi-dimensional optical chemical sensing. Molecular design concepts of the dyes and their fundamental spectral characteristics

AU - Hisamoto, Hideaki

AU - Tohma, Hajime

AU - Yamada, Toshiki

AU - Yamauchi, Ki Ichiro

AU - Siswanta, Dwi

AU - Yoshioka, Naoki

AU - Suzuki, Koji

PY - 1998/11/11

Y1 - 1998/11/11

N2 - The molecular design of multi-functional dyes, called 'multi-information dyes' (MIDs), and their application to several methods of optical chemical sensing were proposed. The concepts for the molecular design of the dyes were as follows: (1) the introduction of multiple (both positive and negative) charges on both ends of the large conjugated π-electron system of the dye molecule, so that the dye interacts with many chemical species or environments; (2) the introduction of different substitution (electron-donating or electron-accepting) groups in the conjugated π-electron system of the dye molecule, so that the dye has a different pK(a) and solvatochromic property; and (3) the introduction of an immobilization site in the dye molecule, so that the dye can be easily prepared as a sensing probe.Based on these concepts, sixteen kinds of dyes were synthesized, all being of the merocyanine type. The basic color-change characteristics of the MIDs were evaluated with a homogeneous system and a solvent extraction two-phase system. Some of these dyes (e.g., KD-M5) offered two-dimensional sensing information for sensing the water content in organic solvents, in which the absorbance maximum wavelength (λ(max)) shift and absorbance change were both utilized as the detecting signals.From these results, the MIDs developed in this study have several possibilities for analytical applications in optical chemical sensing such as pH sensing, ion sensing, neutral molecule sensing, and water content-sensing in organic solvents. Copyright (C) 1998 Elsevier Science B.V.

AB - The molecular design of multi-functional dyes, called 'multi-information dyes' (MIDs), and their application to several methods of optical chemical sensing were proposed. The concepts for the molecular design of the dyes were as follows: (1) the introduction of multiple (both positive and negative) charges on both ends of the large conjugated π-electron system of the dye molecule, so that the dye interacts with many chemical species or environments; (2) the introduction of different substitution (electron-donating or electron-accepting) groups in the conjugated π-electron system of the dye molecule, so that the dye has a different pK(a) and solvatochromic property; and (3) the introduction of an immobilization site in the dye molecule, so that the dye can be easily prepared as a sensing probe.Based on these concepts, sixteen kinds of dyes were synthesized, all being of the merocyanine type. The basic color-change characteristics of the MIDs were evaluated with a homogeneous system and a solvent extraction two-phase system. Some of these dyes (e.g., KD-M5) offered two-dimensional sensing information for sensing the water content in organic solvents, in which the absorbance maximum wavelength (λ(max)) shift and absorbance change were both utilized as the detecting signals.From these results, the MIDs developed in this study have several possibilities for analytical applications in optical chemical sensing such as pH sensing, ion sensing, neutral molecule sensing, and water content-sensing in organic solvents. Copyright (C) 1998 Elsevier Science B.V.

KW - Alcohol sensor

KW - Functional dye

KW - Ion sensor

KW - Optical sensor

KW - Optode

KW - pH sensor

KW - Solvatochromism

KW - Water-content sensor

UR - http://www.scopus.com/inward/record.url?scp=0032508955&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032508955&partnerID=8YFLogxK

U2 - 10.1016/S0003-2670(98)00421-8

DO - 10.1016/S0003-2670(98)00421-8

M3 - Article

AN - SCOPUS:0032508955

VL - 373

SP - 271

EP - 289

JO - Analytica Chimica Acta

JF - Analytica Chimica Acta

SN - 0003-2670

IS - 2-3

ER -