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Issue 40, 2018
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Alternating oligo(o,p-phenylenes) via ruthenium catalyzed diol–diene benzannulation: orthogonality to cross-coupling enables de novo nanographene and PAH construction

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Abstract

Ruthenium(0) catalyzed diol–diene benzannulation is applied to the conversion of oligo(p-phenylene vinylenes) 2a–c, 5 and 6 to alternating oligo(o,p-phenylenes) 10a–c, 11–13. Orthogonality with respect to conventional palladium catalyzed biaryl cross-coupling permits construction of p-bromo-terminated alternating oligo(o,p-phenylenes) 10b, 11–13, which can be engaged in Suzuki cross-coupling and Scholl oxidation. In this way, structurally homogeneous nanographenes 16a–f are prepared. Nanographene 16a, which incorporates 14 fused benzene rings, was characterized by single crystal X-ray diffraction. In a similar fashion, p-bromo-terminated oligo(p-phenylene ethane diol) 9, which contains a 1,3,5-trisubstituted benzene core, is converted to the soluble, structurally homogeneous hexa-peri-hexabenzocoronene 18. A benzothiophene-terminated pentamer 10c was prepared and subjected to Scholl oxidation to furnish the helical bis(benzothiophene)-fused picene derivative 14. The steady-state absorption and emission properties of nanographenes 14, 16a,b,d,e,h and 18 were characterized. These studies illustrate how orthogonality of ruthenium(0) catalyzed diol–diene benzannulation with respect to classical biaryl cross-coupling streamlines oligophenylene and nanographene construction.

Graphical abstract: Alternating oligo(o,p-phenylenes) via ruthenium catalyzed diol–diene benzannulation: orthogonality to cross-coupling enables de novo nanographene and PAH construction

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Publication details

The article was received on 21 Jul 2018, accepted on 17 Aug 2018 and first published on 30 Aug 2018


Article type: Edge Article
DOI: 10.1039/C8SC03236J
Citation: Chem. Sci., 2018,9, 7866-7873
  • Open access: Creative Commons BY license
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    Alternating oligo(o,p-phenylenes) via ruthenium catalyzed diol–diene benzannulation: orthogonality to cross-coupling enables de novo nanographene and PAH construction

    Z. A. Kasun, H. Sato, J. Nie, Y. Mori, J. A. Bender, S. T. Roberts and M. J. Krische, Chem. Sci., 2018, 9, 7866
    DOI: 10.1039/C8SC03236J

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