Spectral Properties and Photochromic Characteristics of Spiropyran Dyes

Kai Hua Shen; Jian Guo Han; Gang Zhang; Dong Hoon Choi

doi:10.1016/S1005-9040(06)60151-7

Spectral Properties and Photochromic Characteristics of Spiropyran Dyes

Kai Hua Shen, Jian Guo Han, Gang Zhang, Dong Hoon Choi

Research output: Contribution to journal › Article › peer-review

3 Citations (Scopus)

Abstract

The bis-benzospiropyran (BBSP) and nitro-substituted indoline spirobenzopyrans(SBP) were prepared by following a simple procedure. The reaction mechanism of synthesizing bis-benzospiropyran is discussed. A comparative analysis of the spectral and photochromic properties between SBP and BBSP was carried out with the aid of a PMMA film. The results indicate that chemical structures and UV irradiation played an important role in the spectral and photochromic properties of SBP and BBSP, which would readily affect λ_max of the colored forms and the reversibility. The IR spectra and ¹H NMR spectra of these compounds are used to interpret the photochromic phenomena under different UV irradiations and determine the configurations of SBP and BBSP.

Original language	English
Pages (from-to)	505-509
Number of pages	5
Journal	Chemical Research in Chinese Universities
Volume	22
Issue number	4
DOIs	https://doi.org/10.1016/S1005-9040(06)60151-7
Publication status	Published - 2006 Jul
Externally published	Yes

Bibliographical note

Funding Information:
Since the last decade, a large number of works have concentrated on the photochromic behavior of in- dolinospirobenzopyran dyes"41 . Interest in these com- pounds has been concerned with the reversibility of the transformation between the colorless spiro forms and the colored merocyanines" . Structural modification of these dyes has been an active research area since these compounds were found to have potential applications, including being used as recording, copying and display materials. It was reported that merocyanine dyes, in- cluding spiropyran and merocyanine complexes (BBSP) , were capable of forming molecular aggre- gate~'~"'. A multistep synthesis has been proposed, which started from 5 -amino Fischer base through sever- al tedious steps and was involved with the preparation of bis-Fischer bases. Bis-Fischer bases then reacted with salicylaldehyde to give the corresponding BSPs[*] (Scheme 1 ). In order to control the aggregate growth and there- by prepare a novel bis-benzospiropyran, a simple pre- paration method for bis-benzospiropyran ( BBSP ) and * Supported by the Scientific Research Foundation for the Returned Overseas Chinese Scholars, Ministry of Education( No. 2004-527). * * To whom correspondence should be addressed. E-mail : shen-kh@ yahoo. com. cn

Keywords

Photochromism
Protonation
Spiropyran
UV radiation

ASJC Scopus subject areas

General Chemistry

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10.1016/S1005-9040(06)60151-7

Cite this

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title = "Spectral Properties and Photochromic Characteristics of Spiropyran Dyes",

abstract = "The bis-benzospiropyran (BBSP) and nitro-substituted indoline spirobenzopyrans(SBP) were prepared by following a simple procedure. The reaction mechanism of synthesizing bis-benzospiropyran is discussed. A comparative analysis of the spectral and photochromic properties between SBP and BBSP was carried out with the aid of a PMMA film. The results indicate that chemical structures and UV irradiation played an important role in the spectral and photochromic properties of SBP and BBSP, which would readily affect λmax of the colored forms and the reversibility. The IR spectra and 1H NMR spectra of these compounds are used to interpret the photochromic phenomena under different UV irradiations and determine the configurations of SBP and BBSP.",

keywords = "Photochromism, Protonation, Spiropyran, UV radiation",

author = "Shen, {Kai Hua} and Han, {Jian Guo} and Gang Zhang and Choi, {Dong Hoon}",

note = "Funding Information: Since the last decade, a large number of works have concentrated on the photochromic behavior of in- dolinospirobenzopyran dyes{"}41 . Interest in these com- pounds has been concerned with the reversibility of the transformation between the colorless spiro forms and the colored merocyanines{"} . Structural modification of these dyes has been an active research area since these compounds were found to have potential applications, including being used as recording, copying and display materials. It was reported that merocyanine dyes, in- cluding spiropyran and merocyanine complexes (BBSP) , were capable of forming molecular aggre- gate~'~{"}'. A multistep synthesis has been proposed, which started from 5 -amino Fischer base through sever- al tedious steps and was involved with the preparation of bis-Fischer bases. Bis-Fischer bases then reacted with salicylaldehyde to give the corresponding BSPs[*] (Scheme 1 ). In order to control the aggregate growth and there- by prepare a novel bis-benzospiropyran, a simple pre- paration method for bis-benzospiropyran ( BBSP ) and * Supported by the Scientific Research Foundation for the Returned Overseas Chinese Scholars, Ministry of Education( No. 2004-527). * * To whom correspondence should be addressed. E-mail : shen-kh@ yahoo. com. cn",

year = "2006",

month = jul,

doi = "10.1016/S1005-9040(06)60151-7",

language = "English",

volume = "22",

pages = "505--509",

journal = "Chemical Research in Chinese Universities",

issn = "1005-9040",

publisher = "Springer International Publishing AG",

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T1 - Spectral Properties and Photochromic Characteristics of Spiropyran Dyes

AU - Shen, Kai Hua

AU - Han, Jian Guo

AU - Zhang, Gang

AU - Choi, Dong Hoon

N1 - Funding Information: Since the last decade, a large number of works have concentrated on the photochromic behavior of in- dolinospirobenzopyran dyes"41 . Interest in these com- pounds has been concerned with the reversibility of the transformation between the colorless spiro forms and the colored merocyanines" . Structural modification of these dyes has been an active research area since these compounds were found to have potential applications, including being used as recording, copying and display materials. It was reported that merocyanine dyes, in- cluding spiropyran and merocyanine complexes (BBSP) , were capable of forming molecular aggre- gate~'~"'. A multistep synthesis has been proposed, which started from 5 -amino Fischer base through sever- al tedious steps and was involved with the preparation of bis-Fischer bases. Bis-Fischer bases then reacted with salicylaldehyde to give the corresponding BSPs[*] (Scheme 1 ). In order to control the aggregate growth and there- by prepare a novel bis-benzospiropyran, a simple pre- paration method for bis-benzospiropyran ( BBSP ) and * Supported by the Scientific Research Foundation for the Returned Overseas Chinese Scholars, Ministry of Education( No. 2004-527). * * To whom correspondence should be addressed. E-mail : shen-kh@ yahoo. com. cn

PY - 2006/7

Y1 - 2006/7

N2 - The bis-benzospiropyran (BBSP) and nitro-substituted indoline spirobenzopyrans(SBP) were prepared by following a simple procedure. The reaction mechanism of synthesizing bis-benzospiropyran is discussed. A comparative analysis of the spectral and photochromic properties between SBP and BBSP was carried out with the aid of a PMMA film. The results indicate that chemical structures and UV irradiation played an important role in the spectral and photochromic properties of SBP and BBSP, which would readily affect λmax of the colored forms and the reversibility. The IR spectra and 1H NMR spectra of these compounds are used to interpret the photochromic phenomena under different UV irradiations and determine the configurations of SBP and BBSP.

AB - The bis-benzospiropyran (BBSP) and nitro-substituted indoline spirobenzopyrans(SBP) were prepared by following a simple procedure. The reaction mechanism of synthesizing bis-benzospiropyran is discussed. A comparative analysis of the spectral and photochromic properties between SBP and BBSP was carried out with the aid of a PMMA film. The results indicate that chemical structures and UV irradiation played an important role in the spectral and photochromic properties of SBP and BBSP, which would readily affect λmax of the colored forms and the reversibility. The IR spectra and 1H NMR spectra of these compounds are used to interpret the photochromic phenomena under different UV irradiations and determine the configurations of SBP and BBSP.

KW - Photochromism

KW - Protonation

KW - Spiropyran

KW - UV radiation

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SN - 1005-9040

VL - 22

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JO - Chemical Research in Chinese Universities

JF - Chemical Research in Chinese Universities

IS - 4

ER -

Spectral Properties and Photochromic Characteristics of Spiropyran Dyes

Abstract

Bibliographical note

Keywords

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