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Issue 9, 2018
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A novel symmetrically multifunctionalized dodecamethoxy-cycloparaphenylene: synthesis, photophysical, and supramolecular properties

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Abstract

In the present study, we report the synthesis of a novel symmetrically multifunctionalized cycloparaphenylene (CPP), dodecamethoxy-[9]CPP (ring[9]arene), through nickel-mediated macrocyclization and subsequent reductive aromatization reactions. The electron-donating methoxy groups were introduced onto the curved precursor at an early stage to avoid the problem of non-selective functionalization of CPPs. Compared to [9]CPP, the present dodecamethoxy-[9]CPP shows a significant red shift (>73 nm) in the fluorescence spectrum. In addition, theoretical calculations revealed its increased torsion angles and ring strain (71.01 kcal mol−1) compared with its unsubstituted counterpart.

Graphical abstract: A novel symmetrically multifunctionalized dodecamethoxy-cycloparaphenylene: synthesis, photophysical, and supramolecular properties

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The article was received on 12 Jan 2018, accepted on 02 Mar 2018 and first published on 05 Mar 2018


Article type: Research Article
DOI: 10.1039/C8QO00033F
Citation: Org. Chem. Front., 2018,5, 1446-1451
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    A novel symmetrically multifunctionalized dodecamethoxy-cycloparaphenylene: synthesis, photophysical, and supramolecular properties

    D. Lu, G. Zhuang, H. Jia, J. Wang, Q. Huang, S. Cui and P. Du, Org. Chem. Front., 2018, 5, 1446
    DOI: 10.1039/C8QO00033F

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