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Molecular lambda shape light-driven dual switches: Spectroscopic and computational studies of the photoisomerization of bisazo Tröger base analogs.

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Title: Molecular lambda shape light-driven dual switches: Spectroscopic and computational studies of the photoisomerization of bisazo Tröger base analogs.
Authors: Kazem-Rostami, Masoud1 masoud.kazem-rostami@hdr.mq.edu.au, Akhmedov, Novruz G.1,2, Faramarzi, Sadegh2
Source: Journal of Molecular Structure. Feb2019, Vol. 1178, p538-543. 6p.
Subjects: Photoisomerization, Stereoisomerism, Crystallography, Molecular structure, Thermal analysis
Abstract: Abstract Bisazo Tröger base analogs are claw-looking molecules that carry two identical but independent photoswitching groups. These bisazo compounds, like dual switches, can be at EE , EZ , and ZZ photoisomerization states while the ∧-shape void of Tröger base scaffold may also introduce an additional possibility of stereoisomerism by holding the photoisomerizable groups in endo or exo positions. To date, the exact molecular geometries of the isomerizable analogs of Tröger's base have not been elaborated. Owing to the special features and potential applications of these molecules, herein their photoisomerization is probed. The gleaned data from 15N isotope labeling and a variety of spectroscopic, spectrophotometric, crystallographic, and computational techniques have revealed the structure of the studied photoisomers and suggested their use in the design of molecular pull and push mechanisms, light driven actuators, and artificial muscles. Graphical abstract Image 1 Highlights • Bisazo Tröger base analogs as dual switches have EE , EZ , and ZZ states. • X-ray analysis of the EE revealed an extended ∧-shape structure of Tröger base. • TLC and 1H NMR confirmed the stepwise conversion of EE–EZ and EZ–ZZ. • FT-IR, 15N NMR and UV–vis displayed photonic E–Z and thermal Z–E conversions. • QM calculations showed that the EE contraction to ZZ is about 60% lengthwise. [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.)
Database: Engineering Source
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DbLabel: Engineering Source
An: 133068000
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  Data: Molecular lambda shape light-driven dual switches: Spectroscopic and computational studies of the photoisomerization of bisazo Tröger base analogs.
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  Data: <searchLink fieldCode="AR" term="%22Kazem-Rostami%2C+Masoud%22">Kazem-Rostami, Masoud</searchLink><relatesTo>1</relatesTo><i> masoud.kazem-rostami@hdr.mq.edu.au</i><br /><searchLink fieldCode="AR" term="%22Akhmedov%2C+Novruz+G%2E%22">Akhmedov, Novruz G.</searchLink><relatesTo>1,2</relatesTo><br /><searchLink fieldCode="AR" term="%22Faramarzi%2C+Sadegh%22">Faramarzi, Sadegh</searchLink><relatesTo>2</relatesTo>
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  Data: <searchLink fieldCode="JN" term="%22Journal+of+Molecular+Structure%22">Journal of Molecular Structure</searchLink>. Feb2019, Vol. 1178, p538-543. 6p.
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  Data: <searchLink fieldCode="DE" term="%22Photoisomerization%22">Photoisomerization</searchLink><br /><searchLink fieldCode="DE" term="%22Stereoisomerism%22">Stereoisomerism</searchLink><br /><searchLink fieldCode="DE" term="%22Crystallography%22">Crystallography</searchLink><br /><searchLink fieldCode="DE" term="%22Molecular+structure%22">Molecular structure</searchLink><br /><searchLink fieldCode="DE" term="%22Thermal+analysis%22">Thermal analysis</searchLink>
– Name: Abstract
  Label: Abstract
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  Data: Abstract Bisazo Tröger base analogs are claw-looking molecules that carry two identical but independent photoswitching groups. These bisazo compounds, like dual switches, can be at EE , EZ , and ZZ photoisomerization states while the ∧-shape void of Tröger base scaffold may also introduce an additional possibility of stereoisomerism by holding the photoisomerizable groups in endo or exo positions. To date, the exact molecular geometries of the isomerizable analogs of Tröger's base have not been elaborated. Owing to the special features and potential applications of these molecules, herein their photoisomerization is probed. The gleaned data from 15N isotope labeling and a variety of spectroscopic, spectrophotometric, crystallographic, and computational techniques have revealed the structure of the studied photoisomers and suggested their use in the design of molecular pull and push mechanisms, light driven actuators, and artificial muscles. Graphical abstract Image 1 Highlights • Bisazo Tröger base analogs as dual switches have EE , EZ , and ZZ states. • X-ray analysis of the EE revealed an extended ∧-shape structure of Tröger base. • TLC and 1H NMR confirmed the stepwise conversion of EE–EZ and EZ–ZZ. • FT-IR, 15N NMR and UV–vis displayed photonic E–Z and thermal Z–E conversions. • QM calculations showed that the EE contraction to ZZ is about 60% lengthwise. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  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.2018.10.071
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      – Code: eng
        Text: English
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        PageCount: 6
        StartPage: 538
    Subjects:
      – SubjectFull: Photoisomerization
        Type: general
      – SubjectFull: Stereoisomerism
        Type: general
      – SubjectFull: Crystallography
        Type: general
      – SubjectFull: Molecular structure
        Type: general
      – SubjectFull: Thermal analysis
        Type: general
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      – TitleFull: Molecular lambda shape light-driven dual switches: Spectroscopic and computational studies of the photoisomerization of bisazo Tröger base analogs.
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            NameFull: Kazem-Rostami, Masoud
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            NameFull: Akhmedov, Novruz G.
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            NameFull: Faramarzi, Sadegh
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              Text: Feb2019
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              Y: 2019
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              Value: 1178
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