Molecular design, characterization, and application of multiinformation dyes for optical chemical sensing: IV. Multiinformation dyes with extended spectral sensitivity in the near-infrared spectral range

Daniel Citterio, Takashi Kawada, Jun Yagi, Tomonori Ishigaki, Hideaki Hisamoto, Shin Ichi Sasaki, Koji Suzuki

研究成果: Article

17 引用 (Scopus)

抄録

In this paper, new "multiinformation dyes" (MIDs) with extended spectral sensitivity reporting on both changes in solvent polarity (solvatochromism) and in pH (halochromism) by changes in their visible absorption spectra, are presented. The merocyanine dyes 2,6-dibromo-4-[4-(1-dodecyl-4(1H)-pyridinylidene)-2-butenylidene]-2,5- cyclohexadien-1-one (KD-M301) and 2,6-dibromo-4-[4-(1-dodecyl-4(1H)-quinolinylidene)-2-butenylidene]-2,5- cyclohexadien-1-one (KD-M402) were designed, synthesized, and characterized regarding analytical applications. The spectral sensitivity for the MIDs was extended into the near-infrared (NIR) wavelength range (λmax = 800 nm in CHCl3 for KD-M402) and at the same time, the degree of solvent polarity-induced spectral shifts was strongly enhanced (Δλmax = 202 nm for KD-M402 between tetrahydrofuran (THF) and methanol), reaching similar values to the standard solvatochromic dye Dimroth-Reichardt's betaine on which the empirical ET(30) classification of solvent polarity is based. Compared to Dimroth-Reichardt's betaine dye, the molar absorption coefficient ε, is increased more than 10-fold (ε of KD-M402 in THF: 7.7 × 104 M-1 cm-1), allowing sensitive measurements at low concentrations of the dye. The dodecyl-substituted KD-M402 is suitable as a lipophilic pH indicator in ion-exchange type optical sensors (optodes) with optical detection in the near-infrared wavelength range.

元の言語English
ページ(範囲)19-28
ページ数10
ジャーナルAnalytica Chimica Acta
482
発行部数1
DOI
出版物ステータスPublished - 2003 4 10
外部発表Yes

Fingerprint

Betaine
dye
near infrared
Coloring Agents
Infrared radiation
Ion Exchange
Wavelength
Methanol
Optical sensors
wavelength
Absorption spectra
Ion exchange
absorption coefficient
absorption spectrum
methanol
chemical
ion exchange
sensor
fold
2,6-diphenyl-4-(2,4,6-triphenyl-1-pyridinio)phenolate

ASJC Scopus subject areas

  • Biochemistry
  • Analytical Chemistry
  • Spectroscopy
  • Environmental Chemistry

これを引用

Molecular design, characterization, and application of multiinformation dyes for optical chemical sensing : IV. Multiinformation dyes with extended spectral sensitivity in the near-infrared spectral range. / Citterio, Daniel; Kawada, Takashi; Yagi, Jun; Ishigaki, Tomonori; Hisamoto, Hideaki; Sasaki, Shin Ichi; Suzuki, Koji.

:: Analytica Chimica Acta, 巻 482, 番号 1, 10.04.2003, p. 19-28.

研究成果: Article

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T1 - Molecular design, characterization, and application of multiinformation dyes for optical chemical sensing

T2 - IV. Multiinformation dyes with extended spectral sensitivity in the near-infrared spectral range

AU - Citterio, Daniel

AU - Kawada, Takashi

AU - Yagi, Jun

AU - Ishigaki, Tomonori

AU - Hisamoto, Hideaki

AU - Sasaki, Shin Ichi

AU - Suzuki, Koji

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N2 - In this paper, new "multiinformation dyes" (MIDs) with extended spectral sensitivity reporting on both changes in solvent polarity (solvatochromism) and in pH (halochromism) by changes in their visible absorption spectra, are presented. The merocyanine dyes 2,6-dibromo-4-[4-(1-dodecyl-4(1H)-pyridinylidene)-2-butenylidene]-2,5- cyclohexadien-1-one (KD-M301) and 2,6-dibromo-4-[4-(1-dodecyl-4(1H)-quinolinylidene)-2-butenylidene]-2,5- cyclohexadien-1-one (KD-M402) were designed, synthesized, and characterized regarding analytical applications. The spectral sensitivity for the MIDs was extended into the near-infrared (NIR) wavelength range (λmax = 800 nm in CHCl3 for KD-M402) and at the same time, the degree of solvent polarity-induced spectral shifts was strongly enhanced (Δλmax = 202 nm for KD-M402 between tetrahydrofuran (THF) and methanol), reaching similar values to the standard solvatochromic dye Dimroth-Reichardt's betaine on which the empirical ET(30) classification of solvent polarity is based. Compared to Dimroth-Reichardt's betaine dye, the molar absorption coefficient ε, is increased more than 10-fold (ε of KD-M402 in THF: 7.7 × 104 M-1 cm-1), allowing sensitive measurements at low concentrations of the dye. The dodecyl-substituted KD-M402 is suitable as a lipophilic pH indicator in ion-exchange type optical sensors (optodes) with optical detection in the near-infrared wavelength range.

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KW - Ion optode

KW - Near-infrared

KW - Optical sensor

KW - pH indicator

KW - Solvatochromism

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