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To what extent are the photophysical properties of quinoxaline- and quinoxalinone-based chromophores predictable?

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Title: To what extent are the photophysical properties of quinoxaline- and quinoxalinone-based chromophores predictable?
Authors: Burganov, Timur I.1 (AUTHOR) timk90@mail.ru, Katsyuba, Sergey A.1 (AUTHOR), Islamova, Liliya N.1 (AUTHOR), Fazleeva, Guzyal M.1 (AUTHOR), Sharipova, Sirina M.1 (AUTHOR), Kalinin, Alexey A.1 (AUTHOR), Monari, Antonio2 (AUTHOR), Assfeld, Xavier2 (AUTHOR)
Source: Dyes & Pigments. Nov2019, Vol. 170, p107580-107580. 1p.
Subjects: Chemical models, Absorption spectra, Intramolecular proton transfer reactions, Chemical structure, Molecular spectra, Chromophores
Abstract: A series of chromophores containing quinoxaline or quinoxalinone electron-acceptor (A) and dialkylaminostyryl electron-donor (D) units linked by π electronic bridge has been synthesized. Electronic emission and absorption spectra of the novel D-π-A, D-π-A-π-D or D-π-A-π-A-π-D systems cover a broad range from ultraviolet to near infrared. Positions and relative intensities of their absorption bands are shown to depend strongly on structural modifications of the molecules, while emission in solution strongly depends on both the structure of the solute and the solvent polarity. Quantum chemical modeling provided a reliable description of the observed absorption spectra and reproduced the positions of the emission bands. Quantum yields of emission are shown to be qualitatively predictable on the basis of empirical rules connecting the luminescence intensity with the chemical structures of both quinoxaline- and quinoxalinone-based luminopohores and the polarity of the solvents used. Theoretical assessment of the character of the main electronic transitions suggests that simultaneous presence of D and A units conjugated via π-bridges ensures the intramolecular charge-transfer effects probably underlying the observed similar solvatochromism for all the studied systems irrespective of their polarity. • A series of novel quinoxaline- and quinoxalinone-based chromophores is synthesized. • Absorption/emission of the chromophores span from the UV to the NIR. • The absorption spectra are reliably simulated quantum chemically. • The positions of the emission bands are also reproduced by the computations. • Quantum yields of emission are qualitatively predictable by empirical rules. [ABSTRACT FROM AUTHOR]
Copyright of Dyes & Pigments 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.)
Database: Engineering Source
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DbLabel: Engineering Source
An: 137625220
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
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  Data: To what extent are the photophysical properties of quinoxaline- and quinoxalinone-based chromophores predictable?
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  Data: <searchLink fieldCode="AR" term="%22Burganov%2C+Timur+I%2E%22">Burganov, Timur I.</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> timk90@mail.ru</i><br /><searchLink fieldCode="AR" term="%22Katsyuba%2C+Sergey+A%2E%22">Katsyuba, Sergey A.</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Islamova%2C+Liliya+N%2E%22">Islamova, Liliya N.</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Fazleeva%2C+Guzyal+M%2E%22">Fazleeva, Guzyal M.</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Sharipova%2C+Sirina+M%2E%22">Sharipova, Sirina M.</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Kalinin%2C+Alexey+A%2E%22">Kalinin, Alexey A.</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Monari%2C+Antonio%22">Monari, Antonio</searchLink><relatesTo>2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Assfeld%2C+Xavier%22">Assfeld, Xavier</searchLink><relatesTo>2</relatesTo> (AUTHOR)
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  Data: <searchLink fieldCode="JN" term="%22Dyes+%26+Pigments%22">Dyes & Pigments</searchLink>. Nov2019, Vol. 170, p107580-107580. 1p.
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  Data: <searchLink fieldCode="DE" term="%22Chemical+models%22">Chemical models</searchLink><br /><searchLink fieldCode="DE" term="%22Absorption+spectra%22">Absorption spectra</searchLink><br /><searchLink fieldCode="DE" term="%22Intramolecular+proton+transfer+reactions%22">Intramolecular proton transfer reactions</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+structure%22">Chemical structure</searchLink><br /><searchLink fieldCode="DE" term="%22Molecular+spectra%22">Molecular spectra</searchLink><br /><searchLink fieldCode="DE" term="%22Chromophores%22">Chromophores</searchLink>
– Name: Abstract
  Label: Abstract
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  Data: A series of chromophores containing quinoxaline or quinoxalinone electron-acceptor (A) and dialkylaminostyryl electron-donor (D) units linked by π electronic bridge has been synthesized. Electronic emission and absorption spectra of the novel D-π-A, D-π-A-π-D or D-π-A-π-A-π-D systems cover a broad range from ultraviolet to near infrared. Positions and relative intensities of their absorption bands are shown to depend strongly on structural modifications of the molecules, while emission in solution strongly depends on both the structure of the solute and the solvent polarity. Quantum chemical modeling provided a reliable description of the observed absorption spectra and reproduced the positions of the emission bands. Quantum yields of emission are shown to be qualitatively predictable on the basis of empirical rules connecting the luminescence intensity with the chemical structures of both quinoxaline- and quinoxalinone-based luminopohores and the polarity of the solvents used. Theoretical assessment of the character of the main electronic transitions suggests that simultaneous presence of D and A units conjugated via π-bridges ensures the intramolecular charge-transfer effects probably underlying the observed similar solvatochromism for all the studied systems irrespective of their polarity. • A series of novel quinoxaline- and quinoxalinone-based chromophores is synthesized. • Absorption/emission of the chromophores span from the UV to the NIR. • The absorption spectra are reliably simulated quantum chemically. • The positions of the emission bands are also reproduced by the computations. • Quantum yields of emission are qualitatively predictable by empirical rules. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Dyes & Pigments 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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        Value: 10.1016/j.dyepig.2019.107580
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      – Code: eng
        Text: English
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      – SubjectFull: Absorption spectra
        Type: general
      – SubjectFull: Intramolecular proton transfer reactions
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      – SubjectFull: Chemical structure
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      – SubjectFull: Molecular spectra
        Type: general
      – SubjectFull: Chromophores
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      – TitleFull: To what extent are the photophysical properties of quinoxaline- and quinoxalinone-based chromophores predictable?
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              M: 11
              Text: Nov2019
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              Y: 2019
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