Nonadditive Substituent Effects on Expanding Prestrained C–C Bond in Crystal: X-ray Analyses on Unsymmetrically Substituted Tetraarylpyracenes Prepared by a Flow Microreactor Method

• Takanori Suzuki

  Department of Chemistry, Faculty of Science, Hokkaido University

• Yasuto Uchimura

  Department of Chemistry, Faculty of Science, Hokkaido University

• Yusuke Ishigaki

  Department of Chemistry, Faculty of Science, Hokkaido University

• Takashi Takeda

  Department of Chemistry, Faculty of Science, Hokkaido University

• Ryo Katoono

  Department of Chemistry, Faculty of Science, Hokkaido University

• Hidetoshi Kawai

  Department of Chemistry, Faculty of Science, Hokkaido University

• Kenshu Fujiwara

  Department of Chemistry, Faculty of Science, Hokkaido University

• Aiichiro Nagaki

  Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University

• Jun-ichi Yoshida

  Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University

Abstract

Based on space integration using a flow microreactor system, the title unsymmetrically substituted pyracenes with an extremely long C–C bond [1.714(2)–1.739(4) Å] are readily accessible, whose structures demonstrate nonadditive substituent effects on expanding the polyarylated C1–C2 bond in crystal. The bond lengths rather exhibit correlation with the eclipsing degree of the Csp3–Csp3 bond, which is more affected by the intermolecular factors such as crystal packing.

Journal

• Chemistry Letters

  Chemistry Letters 41 (5), 541-543, 2012-04-28

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360283694088408448
• NII Article ID: 10030619852
• NII Book ID: AA00603318
• DOI: 10.1246/cl.2012.541
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/41/5/541/55634664/cl.2012.541.pdf
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