Photochromic and fluorescence studies of spiropyran indoline derivatives in the presence of acids

Heekyoung Kang, Youn Sik Lee, Eunkyoung Kim, Yongku Kang, Dong Wook Kim, Changjin Lee

Research output: Contribution to journalArticle

Abstract

We synthesized 3′, 3′-dimethyl-1′-octadecyl-6-nitrospiro-[2H-1-benzopyran-2, 2′-indoline] (SP-18) and examined its photochromic behavior and fluorescence in the presence of acid. When strong acids such as HCl and dodecylbenzenesulfonic acid (DBSA) were present, the merocyanine (MC) form generated via heterolytic cleavage of oxygen-carbon bond of the spiropyran (SP) by the irradiation of UV light was protonated to produce the complex MCH +. The MCH+ had a yellow color with the absorption maxima at between 410∼ 430 nm. Since ring-closing reaction of the MC form to produce the SP form was retarded by the protonation of the phenolate in the MC form, MCH+had better stability than the MC. Emission peak of the MCH+form was observed at 645 nm with HCl and 600 nm with DBSA, respectively. Polymethylmethacrylate (PMMA) films containing the MCH + retained about 75% of its original absorbance even after 48 h.

Original languageEnglish
JournalMolecular Crystals and Liquid Crystals
Volume406
DOIs
Publication statusPublished - 2003 Jan 1

Fingerprint

Fluorescence
Derivatives
fluorescence
acids
Acids
Benzopyrans
Protonation
Polymethyl Methacrylate
closing
Ultraviolet radiation
cleavage
Carbon
Irradiation
Oxygen
Color
color
irradiation
indoline
merocyanine
spiropyran

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

Cite this

Kang, Heekyoung ; Lee, Youn Sik ; Kim, Eunkyoung ; Kang, Yongku ; Kim, Dong Wook ; Lee, Changjin. / Photochromic and fluorescence studies of spiropyran indoline derivatives in the presence of acids. In: Molecular Crystals and Liquid Crystals. 2003 ; Vol. 406.
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abstract = "We synthesized 3′, 3′-dimethyl-1′-octadecyl-6-nitrospiro-[2H-1-benzopyran-2, 2′-indoline] (SP-18) and examined its photochromic behavior and fluorescence in the presence of acid. When strong acids such as HCl and dodecylbenzenesulfonic acid (DBSA) were present, the merocyanine (MC) form generated via heterolytic cleavage of oxygen-carbon bond of the spiropyran (SP) by the irradiation of UV light was protonated to produce the complex MCH +. The MCH+ had a yellow color with the absorption maxima at between 410∼ 430 nm. Since ring-closing reaction of the MC form to produce the SP form was retarded by the protonation of the phenolate in the MC form, MCH+had better stability than the MC. Emission peak of the MCH+form was observed at 645 nm with HCl and 600 nm with DBSA, respectively. Polymethylmethacrylate (PMMA) films containing the MCH + retained about 75{\%} of its original absorbance even after 48 h.",
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Photochromic and fluorescence studies of spiropyran indoline derivatives in the presence of acids. / Kang, Heekyoung; Lee, Youn Sik; Kim, Eunkyoung; Kang, Yongku; Kim, Dong Wook; Lee, Changjin.

In: Molecular Crystals and Liquid Crystals, Vol. 406, 01.01.2003.

Research output: Contribution to journalArticle

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T1 - Photochromic and fluorescence studies of spiropyran indoline derivatives in the presence of acids

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AU - Lee, Youn Sik

AU - Kim, Eunkyoung

AU - Kang, Yongku

AU - Kim, Dong Wook

AU - Lee, Changjin

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N2 - We synthesized 3′, 3′-dimethyl-1′-octadecyl-6-nitrospiro-[2H-1-benzopyran-2, 2′-indoline] (SP-18) and examined its photochromic behavior and fluorescence in the presence of acid. When strong acids such as HCl and dodecylbenzenesulfonic acid (DBSA) were present, the merocyanine (MC) form generated via heterolytic cleavage of oxygen-carbon bond of the spiropyran (SP) by the irradiation of UV light was protonated to produce the complex MCH +. The MCH+ had a yellow color with the absorption maxima at between 410∼ 430 nm. Since ring-closing reaction of the MC form to produce the SP form was retarded by the protonation of the phenolate in the MC form, MCH+had better stability than the MC. Emission peak of the MCH+form was observed at 645 nm with HCl and 600 nm with DBSA, respectively. Polymethylmethacrylate (PMMA) films containing the MCH + retained about 75% of its original absorbance even after 48 h.

AB - We synthesized 3′, 3′-dimethyl-1′-octadecyl-6-nitrospiro-[2H-1-benzopyran-2, 2′-indoline] (SP-18) and examined its photochromic behavior and fluorescence in the presence of acid. When strong acids such as HCl and dodecylbenzenesulfonic acid (DBSA) were present, the merocyanine (MC) form generated via heterolytic cleavage of oxygen-carbon bond of the spiropyran (SP) by the irradiation of UV light was protonated to produce the complex MCH +. The MCH+ had a yellow color with the absorption maxima at between 410∼ 430 nm. Since ring-closing reaction of the MC form to produce the SP form was retarded by the protonation of the phenolate in the MC form, MCH+had better stability than the MC. Emission peak of the MCH+form was observed at 645 nm with HCl and 600 nm with DBSA, respectively. Polymethylmethacrylate (PMMA) films containing the MCH + retained about 75% of its original absorbance even after 48 h.

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