5 years ago

Synthesis and Properties of Covalently Linked AzaBODIPY–BODIPY Dyads and AzaBODIPY-(BODIPY)2 Triads

Synthesis and Properties of Covalently Linked AzaBODIPY–BODIPY Dyads and AzaBODIPY-(BODIPY)2 Triads
Sunit Kumar, Kishor G. Thorat, Mangalampalli Ravikanth
The azaBODIPYs containing one and two formyl functional groups on the 1,7-aryl groups present at the azaBODIPY core were synthesized over sequence of steps and characterized by mass, NMR, absorption, and electrochemical techniques. The monoformylated and diformylated azaBODIPYs are very useful synthons to prepare a wide variety of new fluorescent compounds. The mono- and diformylated azaBODIPYs were treated with pyrrole under mild acidic conditions followed by column chromatographic purification to afford azaBODIPYs appended with one and two dipyrromethanyl groups. The dipyrramethanyl groups of azaBODIPYs were oxidized with DDQ and complexed with BF3·Et2O to obtain covalently linked azaBODIPY–BODIPY dyads and azaBODIPY-(BODIPY)2 triads. The dyads and triads were characterized in detail by HR-MS, 1D and 2D NMR, absorption, fluorescence, and electrochemical techniques and the structure of one of the triads was deduced by X-ray crystallography. The crystal structure of azaBODIPY-(BODIPY)2 triad revealed that the two BODIPY units were in perpendicular orientation with azaBODIPY unit. The absorption and electrochemical studies indicated a weak interaction among the BODIPY and azaBODIPY moieties and the moieties retain their independent characteristic features in dyads and triads. The preliminary fluorescence studies supported an efficient energy transfer from BODIPY unit(s) to azaBODIPY unit in dyads and triads.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00542

DOI: 10.1021/acs.joc.7b00542

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.