6533b821fe1ef96bd127adcc
RESEARCH PRODUCT
A crystalline radical cation derived from Thiele’s hydrocarbon with redox range beyond 1 V
Simon AldridgeCaitilín McmanusAndreas HeilmannYing Kai LohPetra VaskoWilliam K. Myerssubject
Electronic materialsRadicalScienceGeneral Physics and Astronomy010402 general chemistryPhotochemistryvapaat radikaalit01 natural sciencesRedoxArticleGeneral Biochemistry Genetics and Molecular Biologychemistry.chemical_compoundhapetus-pelkistysreaktiochemistry.chemical_classificationRange (particle radiation)kemiallinen synteesiMultidisciplinary010405 organic chemistryQkationitfood and beveragesGeneral Chemistryhiilivedyt0104 chemical sciencesDicationHydrocarbonRadical ionchemistryYield (chemistry)CarbeneInorganic chemistrydescription
Thiele’s hydrocarbon occupies a central role as an open-shell platform for new organic materials, however little is known about its redox behaviour. While recent synthetic approaches involving symmetrical carbene substitution of the CPh2 termini yield isolable neutral/dicationic analogues, the intervening radical cations are much more difficult to isolate, due to narrow compatible redox ranges (typically 1 V), permitting its isolation in crystalline form. Further single-electron oxidation affords borenium dication 12+, thereby establishing an organoboron redox system fully characterized in all three redox states. We perceive that this strategy can be extended to other transient organic radicals to widen their redox stability window and facilitate their isolation.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2021-12-01 |