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Synthesis and properties of azonaphtharylamide pigments having arylamide groups at 2- and 7-positions.

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Title: Synthesis and properties of azonaphtharylamide pigments having arylamide groups at 2- and 7-positions.
Authors: Otani, Junji1, Kikuchi, Takeshi2, Higashida, Suguru3, Harada, Takashi1, Matsumura, Michio1
Source: Journal of Molecular Structure. Mar2015, Vol. 1084, p28-35. 8p.
Subjects: Amide synthesis, Naphthol, Ring formation (Chemistry), Hyperchromic effect, Chromophores, Substituents (Chemistry)
Abstract: We studied two azonaphtharylamide pigments having arylamide groups at the 2- and 7-positions on the naphthol ring. Presence of the 7-substited amide group distinguishes the pigments from conventional azonaphtharylamide pigments derived from 3-hydroxy-2-naphthoic acid. The 7-substituent caused a hyperchromic effect but did not produce bathochromic shift in the optical absorption spectra in solution compared with the corresponding 7-unsubstituted counterparts. Molecular geometry optimizations through semi-empirical MO calculations showed that extent of the chromophore systems in the pigments with and without the 7-substituent is nearly the same, which is consistent with absence of the bathochromic shift. The MO calculations also showed that the MOs localized in the 7-substituents are involved in the electronic transitions in the longest wavelength bands of the pigments, which is responsible for the hyperchromic effect. The 7-substituted pigments exhibited better resistivity to light and heat than the 7-unsubstituted ones. [ABSTRACT FROM AUTHOR]
Copyright of Journal of Molecular Structure is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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DbLabel: Engineering Source
An: 100849987
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  Data: Synthesis and properties of azonaphtharylamide pigments having arylamide groups at 2- and 7-positions.
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  Data: <searchLink fieldCode="AR" term="%22Otani%2C+Junji%22">Otani, Junji</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Kikuchi%2C+Takeshi%22">Kikuchi, Takeshi</searchLink><relatesTo>2</relatesTo><br /><searchLink fieldCode="AR" term="%22Higashida%2C+Suguru%22">Higashida, Suguru</searchLink><relatesTo>3</relatesTo><br /><searchLink fieldCode="AR" term="%22Harada%2C+Takashi%22">Harada, Takashi</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Matsumura%2C+Michio%22">Matsumura, Michio</searchLink><relatesTo>1</relatesTo>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Molecular+Structure%22">Journal of Molecular Structure</searchLink>. Mar2015, Vol. 1084, p28-35. 8p.
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  Data: <searchLink fieldCode="DE" term="%22Amide+synthesis%22">Amide synthesis</searchLink><br /><searchLink fieldCode="DE" term="%22Naphthol%22">Naphthol</searchLink><br /><searchLink fieldCode="DE" term="%22Ring+formation+%28Chemistry%29%22">Ring formation (Chemistry)</searchLink><br /><searchLink fieldCode="DE" term="%22Hyperchromic+effect%22">Hyperchromic effect</searchLink><br /><searchLink fieldCode="DE" term="%22Chromophores%22">Chromophores</searchLink><br /><searchLink fieldCode="DE" term="%22Substituents+%28Chemistry%29%22">Substituents (Chemistry)</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: We studied two azonaphtharylamide pigments having arylamide groups at the 2- and 7-positions on the naphthol ring. Presence of the 7-substited amide group distinguishes the pigments from conventional azonaphtharylamide pigments derived from 3-hydroxy-2-naphthoic acid. The 7-substituent caused a hyperchromic effect but did not produce bathochromic shift in the optical absorption spectra in solution compared with the corresponding 7-unsubstituted counterparts. Molecular geometry optimizations through semi-empirical MO calculations showed that extent of the chromophore systems in the pigments with and without the 7-substituent is nearly the same, which is consistent with absence of the bathochromic shift. The MO calculations also showed that the MOs localized in the 7-substituents are involved in the electronic transitions in the longest wavelength bands of the pigments, which is responsible for the hyperchromic effect. The 7-substituted pigments exhibited better resistivity to light and heat than the 7-unsubstituted ones. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
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  Group: Ab
  Data: <i>Copyright of Journal of Molecular Structure is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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      – Type: doi
        Value: 10.1016/j.molstruc.2014.12.011
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      – Code: eng
        Text: English
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        PageCount: 8
        StartPage: 28
    Subjects:
      – SubjectFull: Amide synthesis
        Type: general
      – SubjectFull: Naphthol
        Type: general
      – SubjectFull: Ring formation (Chemistry)
        Type: general
      – SubjectFull: Hyperchromic effect
        Type: general
      – SubjectFull: Chromophores
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      – SubjectFull: Substituents (Chemistry)
        Type: general
    Titles:
      – TitleFull: Synthesis and properties of azonaphtharylamide pigments having arylamide groups at 2- and 7-positions.
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            NameFull: Otani, Junji
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            NameFull: Kikuchi, Takeshi
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            NameFull: Higashida, Suguru
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            NameFull: Harada, Takashi
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            NameFull: Matsumura, Michio
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              Text: Mar2015
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              Y: 2015
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              Value: 1084
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