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Title: Curved ?-conjugated corannulene dimer diradicaloids
Authors: Wang, Q.
Hu, P. 
Tanaka, T.
Gopalakrishna, T.Y. 
Herng, T.S. 
Phan, H. 
Zeng, W. 
Ding, J. 
Osuka, A.
Chi, C. 
Siegel, J.
Wu, J.
Issue Date: 2018
Publisher: Royal Society of Chemistry
Citation: Wang, Q., Hu, P., Tanaka, T., Gopalakrishna, T.Y., Herng, T.S., Phan, H., Zeng, W., Ding, J., Osuka, A., Chi, C., Siegel, J., Wu, J. (2018). Curved ?-conjugated corannulene dimer diradicaloids. Chemical Science 9 (22) : 5100-5105. ScholarBank@NUS Repository.
Rights: Attribution-NonCommercial 4.0 International
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 singlet-triplet energy gap (?ES-T) of -8.4 and -3.0 kcal mol-1, 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. © 2018 The Royal Society of Chemistry.
Source Title: Chemical Science
ISSN: 2041-6520
DOI: 10.1039/c8sc01388h
Rights: Attribution-NonCommercial 4.0 International
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