[<i>n</i>]Radialenes

Maas, Gerhard

doi:10.1002/9783527671182.ch4

Cross Conjugation 2016

DOI: 10.1002/9783527671182.ch4

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[n]Radialenes

Gerhard Maas¹

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Cited by 9 publications

References 165 publications

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Synthesis and Structural Elucidation of Bisdibenzocorannulene in Multiple Redox States

Yang

Wang

et al. 2021

Angewandte Chemie

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We report an anti‐folded bowl‐shaped bisdibenzocorannulene (BDBC) featuring a new chair‐cyclohexane‐like hexagon as a bridge of two dibenzocorannulene moieties. The neutral compound showed multiple redox‐active properties and could be converted to the corresponding redox states through chemical reduction or oxidation. Chemical reduction of BDBC by stoichiometric addition of metallic potassium in the presence of [18]crown‐6 ether, provided a radical anion BDBC.− and a dianion BDBC2−, respectively; while chemical oxidation by silver hexafluoroantimonate(V), converted the neutral compound to an open‐shell singlet diradical dication (BDBC..)2+. The structural consequences of both electron‐reduction and oxidation were closely related to the release of ring‐strain of the bowl‐shaped π‐scaffold and imposed steric hindrance of the hexagonal bridge. In addition, the unusual open‐shell nature of the dication could mainly be attributed to the changing of localized antiaromaticity in the closed‐shell structure to delocalized character in the biradical, and thus the emergence of weakly bonded π‐electrons.

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Synthesis and Structural Elucidation of Bisdibenzocorannulene in Multiple Redox States

Yang

Wang

et al. 2021

Angewandte Chemie

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α‐Cyano Triaryl[3]radialene: Unsymmetrical Stereo‐configuration, Clustering‐enhanced Excimer Emission, and Radical‐involved Multimodal Information Switching

Liu

Zhou

et al. 2023

Angewandte Chemie

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3]Radialene has a peculiar topology and cross-conjugation system, representing a unique molecular scaffold in organic materials. Herein, we report a special class of stereoisomeric α-cyano triaryl-[3]radialenes (CTRs) that show concentration-caused quenching in solution but emit red-shifted and enhanced luminescence in the crystalline state. Clustering of multiple cyano groups and their through-space interactions with the [3]radialene ring significantly extend π-electron communication meanwhile rigidifying the propeller conformation multivalently, thus playing a key role behind the state-dependent luminescence. These radialenes with a substantial electron affinity undergo a reversible electron transfer transition to anionic radicals with good stability, showing switching of photoabsorption, photoluminescence and electron spin resonance (ESR) signal. We also established proof-of-concept applications of CTRs for multimodal information encryption and chemical sensing.

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Synthesis and Structural Elucidation of Bisdibenzocorannulene in Multiple Redox States

Yang

Wang

et al. 2021

Angew Chem Int Ed

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We report an anti-folded bowl-shaped bisdibenzocorannulene (BDBC)f eaturing an ew chair-cyclohexane-like hexagon as abridge of two dibenzocorannulene moieties.The neutral compound showed multiple redox-active properties and could be converted to the corresponding redox states through chemical reduction or oxidation.C hemical reduction of BDBC by stoichiometric addition of metallic potassium in the presence of [18]crown-6 ether,p rovided ar adical anion BDBCC À and adianion BDBC 2À ,respectively;while chemical oxidation by silver hexafluoroantimonate(V), converted the neutral compound to an open-shell singlet diradical dication (BDBCCC) 2+ .T he structural consequences of both electronreduction and oxidation were closely related to the release of ring-strain of the bowl-shaped p-scaffold and imposed steric hindrance of the hexagonal bridge.I na ddition, the unusual open-shell nature of the dication could mainly be attributed to the changing of localized antiaromaticity in the closed-shell structure to delocalized character in the biradical, and thus the emergence of weakly bonded p-electrons.

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[n]Radialenes

Cited by 9 publications

References 165 publications

Synthesis and Structural Elucidation of Bisdibenzocorannulene in Multiple Redox States

Synthesis and Structural Elucidation of Bisdibenzocorannulene in Multiple Redox States

α‐Cyano Triaryl[3]radialene: Unsymmetrical Stereo‐configuration, Clustering‐enhanced Excimer Emission, and Radical‐involved Multimodal Information Switching

Synthesis and Structural Elucidation of Bisdibenzocorannulene in Multiple Redox States

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