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 journalConference article

1 Citation (Scopus)

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 dodecylbenzene-sulfonic 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 48h.

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sulfonic acid
Fluorescence
Derivatives
fluorescence
acids
Acids
Sulfonic Acids
closing
cleavage
Benzopyrans
color
irradiation
carbon
rings
Protonation
oxygen
Polymethyl Methacrylate
Ultraviolet radiation
Carbon
Irradiation

All Science Journal Classification (ASJC) codes

  • Condensed Matter Physics

Cite this

@article{df13a06cfa00458f9eb594bc22932503,
title = "Photochromic and fluorescence studies of spiropyran indoline derivatives in the presence of acids",
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 dodecylbenzene-sulfonic 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 48h.",
author = "Heekyoung Kang and Lee, {Youn Sik} and Eunkyoung Kim and Yongku Kang and Kim, {Dong Wook} and Changjin Lee",
year = "2003",
month = "12",
day = "1",
doi = "10.1080/15421400390264928",
language = "English",
volume = "406",
journal = "Molecular Crystals and Liquid Crystals",
issn = "1542-1406",
publisher = "Taylor and Francis Ltd.",
number = "PART 2",

}

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 Science and Technology Section A: Molecular Crystals and Liquid Crystals, Vol. 406, No. PART 2, 01.12.2003.

Research output: Contribution to journalConference article

TY - JOUR

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

AU - Kang, Heekyoung

AU - Lee, Youn Sik

AU - Kim, Eunkyoung

AU - Kang, Yongku

AU - Kim, Dong Wook

AU - Lee, Changjin

PY - 2003/12/1

Y1 - 2003/12/1

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 dodecylbenzene-sulfonic 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 48h.

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 dodecylbenzene-sulfonic 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 48h.

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