Curved -conjugated corannulene dimer diradicaloidsElectronic supplementary information (ESI) available: Synthetic procedures and characterization data of all new compounds; details for all physical characterization and theoretical calculations; and additional spectroscopic data. CCDC 1570628, 1819178 and 1819179. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc01388h

Curved -conjugated corannulene dimer diradicaloidsElectronic supplementary information (ESI)... So far, most reported open-shell singlet diradicaloids are based on planar -conjugated molecules. Herein, we report the bridged corannulene dimer diradicaloids, Cor-D1 and Cor-D2, both showing a three-dimensional curved -conjugated structure. Cor-D1 has a small diradical character (y0 = 5.4%) and behaves more like a closed-shell quinoidal compound at room temperature, while Cor-D2 is a typical open-shell diradicaloid with a larger diradical character (y0 = 16.9%). Both compounds exhibited paramagnetic activity at elevated temperatures, with a singlettriplet energy gap (EST) of 8.4 and 3.0 kcal mol1, respectively. X-ray crystallographic analysis revealed that both molecules have a dumbbell-shaped geometry, with the two terminal corannulene bowls bent to opposite directions. The spin is largely delocalized onto the two bowls in Cor-D2 and there are multiple [CH] interactions between the neighboring bowls. Chemical oxidation/reduction to their respective dications/dianions results in global aromaticity with [4n + 2] -electrons delocalized through the periphery of the whole framework. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemical Science Royal Society of Chemistry

Curved -conjugated corannulene dimer diradicaloidsElectronic supplementary information (ESI) available: Synthetic procedures and characterization data of all new compounds; details for all physical characterization and theoretical calculations; and additional spectroscopic data. CCDC 1570628, 1819178 and 1819179. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc01388h

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Publisher
Royal Society of Chemistry
Copyright
This journal is © The Royal Society of Chemistry
ISSN
2041-6520
D.O.I.
10.1039/c8sc01388h
Publisher site
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Abstract

So far, most reported open-shell singlet diradicaloids are based on planar -conjugated molecules. Herein, we report the bridged corannulene dimer diradicaloids, Cor-D1 and Cor-D2, both showing a three-dimensional curved -conjugated structure. Cor-D1 has a small diradical character (y0 = 5.4%) and behaves more like a closed-shell quinoidal compound at room temperature, while Cor-D2 is a typical open-shell diradicaloid with a larger diradical character (y0 = 16.9%). Both compounds exhibited paramagnetic activity at elevated temperatures, with a singlettriplet energy gap (EST) of 8.4 and 3.0 kcal mol1, respectively. X-ray crystallographic analysis revealed that both molecules have a dumbbell-shaped geometry, with the two terminal corannulene bowls bent to opposite directions. The spin is largely delocalized onto the two bowls in Cor-D2 and there are multiple [CH] interactions between the neighboring bowls. Chemical oxidation/reduction to their respective dications/dianions results in global aromaticity with [4n + 2] -electrons delocalized through the periphery of the whole framework.

Journal

Chemical ScienceRoyal Society of Chemistry

Published: May 23, 2018

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