biostudies-literatureKasun ZADivision of ChemistryChina Scholarship CouncilAmerican Chemical SocietyWelch FoundationJapan Student Services Organization7866-7873https://www.ebi.ac.uk/biostudies/studies/S-EPMC6194800biostudies-literatureUnknown9(40)Ruthenium(0) catalyzed diol-diene benzannulation is applied to the conversion of oligo(<i>p</i>-phenylene vinylenes) <b>2a-c</b>, <b>5</b> and <b>6</b> to alternating oligo(<i>o</i>,<i>p</i>-phenylenes) <b>10a-c</b>, <b>11-13</b>. Orthogonality with respect to conventional palladium catalyzed biaryl cross-coupling permits construction of <i>p</i>-bromo-terminated alternating oligo(<i>o</i>,<i>p</i>-phenylenes) <b>10b</b>, <b>11-13</b>, which can be engaged in Suzuki cross-coupling and Scholl oxidation. In this way, structurally homogeneous nanographenes <b>16a-f</b> are prepared. Nanographene <b>16a</b>, which incorporates 14 fused benzene rings, was characterized by single crystal X-ray diffraction. In a similar fashion, <i>p</i>-bromo-terminated oligo(<i>p</i>-phenylene ethane diol) <b>9Chemical scienceAlternating oligo(<i>o</i>,<i>p</i>-phenylenes) <i>via</i> ruthenium catalyzed diol-diene benzannulation: orthogonality to cross-coupling enables <i>de novo</i> nanographene and PAH construction.PMC6194800CHE-1565688F-1885F-0038Bender JAKrische MJKasun ZAMori YNie JRoberts STSato HfalseAlternating oligo(<i>o</i>,<i>p</i>-phenylenes) <i>via</i> ruthenium catalyzed diol-diene benzannulation: orthogonality to cross-coupling enables <i>de novo</i> nanographene and PAH construction.Ruthenium(0) catalyzed diol-diene benzannulation is applied to the conversion of oligo(<i>p</i>-phenylene vinylenes) <b>2a-c</b>, <b>5</b> and <b>6</b> to alternating oligo(<i>o</i>,<i>p</i>-phenylenes) <b>10a-c</b>, <b>11-13</b>. Orthogonality with respect to conventional palladium catalyzed biaryl cross-coupling permits construction of <i>p</i>-bromo-terminated alternating oligo(<i>o</i>,<i>p</i>-phenylenes) <b>10b</b>, <b>11-13</b>, which can be engaged in Suzuki cross-coupling and Scholl oxidation. In this way, structurally homogeneous nanographenes <b>16a-f</b> are prepared. Nanographene <b>16a</b>, which incorporates 14 fused benzene rings, was characterized by single crystal X-ray diffraction. In a similar fashion, <i>p</i>-bromo-terminated oligo(<i>p</i>-phenylene ethane diol) <b>92018-01-01T00:00:00Z2018 Oct2025-04-22T15:59:47.028Z2019-03-27T00:07:30ZS-EPMC61948003042999610.1039/c8sc03236j