Chemistry - An Asian Journal
Chemistry - An Asian Journal
5 years ago

π-Extended Dihydrophenazines with Three-State NIR Electrochromism Involving Large Conformational Changes

π-Extended Dihydrophenazines with Three-State NIR Electrochromism Involving Large Conformational Changes
Hiroshi Shinokubo, Satoru Hiroto, Juri Nagasaki
π-Extended dihydrophenazines were successfully prepared by oxidation of 2-(N-arylamino)anthracenes. Their roof-type conformations were revealed by X-ray diffraction analysis, and the analysis of the optical properties indicated the presence of intramolecular charge-transfer processes. Upon chemical oxidation, the electronic absorption dramatically changed in a two-step fashion. The electron spin resonance (ESR) analysis revealed that, depending on the amount of oxidant added, either a paramagnetic radical cation or a diamagnetic dication was generated. The NMR analysis revealed a conformational change upon oxidation, which was supported by theoretical calculations. A three-state electrochromic behavior was observed during the electrochemical oxidation and reduction cycles, showing sequential switching between visible and near-infrared (NIR) absorption properties upon application of electrochemical stimuli. Getting a piece of the pie: π-Extended dihydrophenanzines were successfully prepared by oxidation of 2-(N-arylamino)anthracenes. They exhibited a dramatic electronic absorption change upon chemical oxidation. The spectroscopic analysis and theoretical investigation revealed a concurrent conformational change. Furthermore, sequential switching between visible and NIR absorption properties by electrochemical stimuli were demonstrated.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/asia.201700840

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.