Abstract
Although aromaticity is a key concept in chemistry that is frequently used to explain the structure and reactivity of organic compounds, it remains challenging to actually measure this property. Proper probes allow for an experimental quantification of aromaticity using nuclear magnetic resonance (NMR) spectroscopy and in this study 15,16-dimethyl-15,16-dihydropyrene (DHP) is demonstrated to be particularly well suited for this purpose. DHP has two internal methyl groups, which are positioned within the π cloud of this bridged, planar, and rigid [14]annulene, and are therefore shifted to higher field in proton NMR spectra owing to ring-current effects. A specific DHP derivative bearing strongly electron-donating dimethylamino and strongly electron-accepting nitro groups in a relative pseudo-para orientation has been synthesized and characterized with respect to its quinoid character. Solvatochromism as well as a reduced ring current show that the partial quinoid character in this push-pull DHP derivative is about 12 %. This study extends the scope of DHP as an aromaticity probe and aids in the better understanding of the phenomenon of aromaticity.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
