Incorporating Cobalt Carbonyl Moieties onto Ethynylthiophene-Based Dithienylcyclopentene Switches. 1. Photochemistry

Emma C. Harvey, Jetsuda Areephong, Attilio A. Cafolla, Conor Long, Wesley R. Browne, Mary T. Pryce*, Bernard Feringa

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

The synthesis and characterization of a series of dithienyl perhydro- and perfluorocyclopentene photochromic molecular switches appended with cobalt carbonyl binding 3-ethynylthiophene and phenyl-3-ethynylthiophene substituents are reported. Their photochromic properties, fatigue resistance, and thermal stability were examined to establish the effect of substituents on their performance as molecular photoswitches. The photochemical properties of the dithienylethene core were retained to the greatest extent by the inclusion of phenyl units and a hexafluorocyclopentene ring. The alkyne units of the switches were used to coordinate cobalt carbonyl moieties: i.e., Co-2(CO)(6) and Co-2(CO)(4)(dppm). The cobalt carbonyl moieties were found to reduce the efficiency of cyclization and cycloreversion of the dithienylethene unit. Density functional theory was used to identify the excited states responsible for cyclization.

Original languageEnglish
Pages (from-to)447-456
Number of pages10
JournalOrganometallics
Volume33
Issue number2
DOIs
Publication statusPublished - 27-Jan-2014

Keywords

  • MOLECULAR-ORBITAL METHODS
  • BY-PRODUCT FORMATION
  • PHOTOCHROMIC DITHIENYLETHENES
  • OPTOELECTRONIC PROPERTIES
  • ENERGY-TRANSFER
  • BASIS-SET
  • PART 2
  • DIARYLETHENE
  • COMPLEXES
  • LIGANDS

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