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

Masoud Kazem-Rostami, Novruz G. Akhmedov, Sadegh Faramarzi

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)538-543
Number of pages6
JournalJournal of Molecular Structure
Volume1178
DOIs
StatePublished - Feb 15 2019

Bibliographical note

Funding Information:
This article is dedicated to Associate Professor Ahmad Reza Moosavi-Zare for his invaluable comments and great companionship. Professor Barbara Messerle and Dr Yuling Wang are thanked for the provided isotope enriched reagents and access to Raman spectrometer, respectively. This work was supported by the Australian Government [ IPRS-2014004 ], and Macquarie University [ HDR43010477 , and PGRF2016R2-1672525 ].

Publisher Copyright:
© 2018 Elsevier B.V.

Keywords

  • Azo compound
  • Light-driven
  • Molecular machine
  • Photoisomerization
  • Photoswitch
  • Tröger base
  • URINXLRVGTUPLS-SWRFNBSLSA-N
  • URINXLRVGTUPLS-ZCSLVFMRSA-N

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