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Bowl-Shaped Symmetric and Non-symmetric Bis-functionalized Indacenopicenes

Bowl-Shaped Symmetric and Non-symmetric Bis-functionalized Indacenopicenes

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BAYER, Johannes, Thomas HUHN, 2022. Bowl-Shaped Symmetric and Non-symmetric Bis-functionalized Indacenopicenes. In: The Journal of Organic Chemistry. American Chemical Society (ACS). 87(8), pp. 5257-5278. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/acs.joc.2c00040

@article{Bayer2022-04-15BowlS-57651, title={Bowl-Shaped Symmetric and Non-symmetric Bis-functionalized Indacenopicenes}, year={2022}, doi={10.1021/acs.joc.2c00040}, number={8}, volume={87}, issn={0022-3263}, journal={The Journal of Organic Chemistry}, pages={5257--5278}, author={Bayer, Johannes and Huhn, Thomas} }

2022-05-25T12:31:52Z Bayer, Johannes 2022-05-25T12:31:52Z Huhn, Thomas eng 2022-04-15 Bayer, Johannes Bowl-Shaped Symmetric and Non-symmetric Bis-functionalized Indacenopicenes Regioselective arrangement of two groups of orthogonal reactivity in bowl-shaped as-indaceno[3,2,1,8,7,6-pqrstuv]picene (Idpc) was key for the synthesis of hetero-bis-functionalized Idpc derivatives. Halogen and methyl groups were positioned at specific positions in the rim area of Idpc at an early stage during the synthesis by functionalization of suitable precursors. Regioselective functionalization of the bowl’s rim was then finally achieved either via consecutive Cu(I)-catalyzed azide–alkyne coupling (CuAAC) and C–C cross-coupling reactions or by C–C cross-coupling alone, giving access to either symmetric or non-symmetric bis-functionalized Idpc derivatives. The self-aggregation behavior of 9c in solution was investigated by recording a series of concentration-dependent NMR spectra. The aggregation constant of 9c was determined by a nonlinear least-squares treatment of the 1H NMR shift data to be 2.9 ± 0.2 M<sup>–1</sup>, and the formation of dimers was found to be the prevailing process. Huhn, Thomas

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