Theoretical Study of the Substituent and Solvent Effects on the Molecular Structures, Absorption and Emission Spectra of Open-Form Spiropyrans

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Title:Theoretical Study of the Substituent and Solvent Effects on the Molecular Structures, Absorption and Emission Spectra of Open-Form Spiropyrans
Creators:
Sheng, Yinghong
Leszczynski, Jerzy
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 1, pp. 47-62
Uncontrolled Keywords:<i>Ab initio</i> calculations, Emission, Spiropyrans, BLA, Photochromism, Time dependent density functional, Solvent effects, DFT, AM1, UV-VIS spectroscopy, Substituent effects

Abstract

The effects of substituents and solvents on the molecular structures, excitation energies and emission energies of a series of donor-acceptor substituted spiropyrans were investigated using the density functional methods. Different donor-acceptor pairs lead to alternations of the molecular structures. A relationship between the strengths of donor-acceptor pairs and the structural parameter BLA (bond length alternation) was examined and discussed. The impact on geometrical parameters induced by the solvents is more significant than that caused by the substituents, as indicated by the larger BLA changes. The substituent and solvent effects on the UV absorption and emission spectra of open-form spiropyrans were studied by the TD-DFT method. The absorption maxima of open-form spiropyrans are expected to red shift, and the emission are expected to blue shift as the strengths of donor-acceptor pairs and the polarities of solvents increase. A simple model was adopted to mimic the substituent and solvent effects, in the framework of AM1, employing Sparkles to create an external electric field on the open-form spiropyran, in order to induce a systematical polarization of the molecular equilibrium geometry and the electronic configuration. <p>

Title:Theoretical Study of the Substituent and Solvent Effects on the Molecular Structures, Absorption and Emission Spectra of Open-Form Spiropyrans
Creators:
Sheng, Yinghong
Leszczynski, Jerzy
Uncontrolled Keywords:<i>Ab initio</i> calculations, Emission, Spiropyrans, BLA, Photochromism, Time dependent density functional, Solvent effects, DFT, AM1, UV-VIS spectroscopy, Substituent effects
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:69
Number:1
Page Range:pp. 47-62
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20040047UNSPECIFIED
ID Code:2195
Item Type:Article
Deposited On:06 Feb 2009 17:16
Last Modified:06 Feb 2009 16:16

Citation

Sheng, Yinghong; Leszczynski, Jerzy (2004) Theoretical Study of the Substituent and Solvent Effects on the Molecular Structures, Absorption and Emission Spectra of Open-Form Spiropyrans. Collection of Czechoslovak Chemical Communications, 69 (1). pp. 47-62. ISSN 0010-0765

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