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Dibenzopentalenes and Related Compounds

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Chemical Science of π-Electron Systems

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Abstract

Conjugated hydrocarbons with polycyclic frameworks have attracted much attention because of their utility in organic electronic devices. Although dibenzopentalenes possess a 4nπ-electron system, they are fairly stable compounds with a planar structure. Thus, appropriate modification would provide them with desirable electronic properties. Recently, we have developed a novel reaction yielding dibenzopentalene derivatives from readily available o-bromoethynylbenzenes using commercially available nickel complexes. The method is accessible to π-extended pentalene derivatives bearing various functional groups and aromatic ring systems. Among them, a dinaphthylpentalene derivative showed a very high hole mobility as amorphous materials. Furthermore, it was employed as a p-type material for organic heterojunction photovoltaic cells. The results indicate that π-extended pentalenes would serve as a good platform for materials applicable to organic electronics.

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References

  1. Anthony JE (2008) Angew Chem Int Ed 47:452–483

    Article  CAS  Google Scholar 

  2. Yamamoto T, Takimiya K (2007) J Am Chem Soc 129:2224–2225

    Article  CAS  Google Scholar 

  3. Takimiya K et al (2011) Adv Mater 23:4347–4370

    Article  CAS  Google Scholar 

  4. Hafner K et al (1973) Angew Chem Int Ed Engl 12:337–339

    Article  Google Scholar 

  5. Hopf H (2000) Classics in hydrocarbon chemistry. Wiley-VCH, Weinheim, New York, Chichester, Brisbane, Singapore, Toronto, pp 277–290

    Google Scholar 

  6. Saito M et al (2008) Chem Eur J 14:6062–6068

    Article  CAS  Google Scholar 

  7. Saito M (2010) Symmetry 2:950–969

    Article  CAS  Google Scholar 

  8. Kawase T et al (2009) Chem Eur J 15:2653–2661

    Article  CAS  Google Scholar 

  9. Kawase T, Takimiya K et al (2010) Angew Chem Int Ed 49:7728–7732

    Article  CAS  Google Scholar 

  10. Brand K (1912) Ber Dtsch Chem Ges 45:3071

    Article  Google Scholar 

  11. Kawase T et al. (2011) Eur J Org Chem 4885–4891; Kawase T (2012) J Synth Org Chem Jan 70:354–365

    Google Scholar 

  12. Youngs WJ et al (1999) J Org Chem 64:2947–2949

    Article  Google Scholar 

  13. Iyoda M et al (2011) Angew Chem Int Ed 50:10522–10553

    Article  CAS  Google Scholar 

  14. Hassan J et al (2002) Chem Rev 102:1359–1470

    Article  CAS  Google Scholar 

  15. Iyoda M, Oda M et al (1990) Bull Chem Soc Jpn 63:80–87

    Article  CAS  Google Scholar 

  16. Ittel SD, Springer W et al (1990) Inorg Synth 28:98–104

    CAS  Google Scholar 

  17. Lee HB, Sharp PR (2005) Organometallics 24:4875–4877

    Article  CAS  Google Scholar 

  18. Levi ZU, Don Tilley T (2009) J Am Chem Soc 131:2796–2797

    Article  CAS  Google Scholar 

  19. Li Y, Zhu D et al (2011) Org Lett 13:1520–1523

    Article  Google Scholar 

  20. Kawase T et al (2010) Chem Lett 39:300–301

    Article  Google Scholar 

  21. Li ZY et al (2007) Synth Commun 37:71–78

    Article  Google Scholar 

  22. The molecular geometries of the dibenzopentalenes were fully optimized at the RB3LYP/6-31G** level of theory embedded in the Gaussian 03 software package

    Google Scholar 

  23. Nishida J, Kawase T et al. unpublished results

    Google Scholar 

  24. Takimiya K et al (2006) J Am Chem Soc 128:12604–12605

    Article  CAS  Google Scholar 

  25. Anthony JE et al (2005) Org Lett 7:3163–3166

    Article  Google Scholar 

  26. Tokito S et al (2004) J Am Chem Soc 126:8138–8140

    Article  Google Scholar 

  27. Takimiya K et al (2010) Bull Chem Soc Jpn 83:120–130

    Article  Google Scholar 

  28. (a) Böuerle P et al (2007) Angew Chem Int Ed 46:1679–1683, (b) Tolbert SH, Schwartz BJ, Rubin Y et al (2008) J Am Chem Soc 130:17290–17292; (c) Matsuo Y, Nakamura E et al (2009) J Am Chem Soc 131:16048–16050

    Google Scholar 

  29. (a) Swager TM et al (2010) Org Lett 12:5302–5305; (b) Kato S, Diederich F (2010) Chem Commun 46:1994–2006; (c) Diederich F et al (2012) J Am Chem Soc 134:18139 − 18146

    Google Scholar 

  30. Heeger AJ, Wudl F et al (2010) Angew Chem Int Ed 49:532–536

    Article  Google Scholar 

  31. (a) Shimizu A, Tobe Y (2011) Angew Chem Int Ed 50:6906–6910; (b) Tobe Y et al (2013) Angew Chem Int Ed 52:6076–6079; (c) Tobe Y et al (2012) Chem Sci 5:163–168

    Google Scholar 

  32. (a) Haley MM et al (2011) Angew Chem Int Ed 50:1127–1162; (b) Haley MM et al (2011) Angew Chem Int Ed 50:11103–11106; (c) Nuckolls C, Haley MM et al (2012) J Am Chem Soc 134:10349 − 10352; (d) Haley MM et al (2014) Chem Sci 5:1008–1014

    Google Scholar 

  33. Nishida J, Yamashita Y et al (2012) Chem Eur J 18:8964–8970

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This study was partly supported by a Grant-in-Aid for Scientific Research on Innovative Areas (Nos. 21108521, 23108718, and 25109515) from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

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Authors and Affiliations

  1. Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo, 671-2280, Japan

    Takeshi Kawase

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  1. Takeshi Kawase
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Correspondence to Takeshi Kawase .

Editor information

Editors and Affiliations

  1. Foundation for Advancement of International Science, Tsukuba, Japan

    Takeshi Akasaka

  2. Kyoto University, Kyoto, Japan

    Atsuhiro Osuka

  3. Department of Chemistry and Nano Science,, Ewha Womans University, Seoul, Korea (Republic of)

    Shunichi Fukuzumi

  4. Nagoya Institute of Technology, Nagoya, Japan

    Hideki Kandori

  5. Osaka University, Suita, Japan

    Yoshio Aso

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Kawase, T. (2015). Dibenzopentalenes and Related Compounds. In: Akasaka, T., Osuka, A., Fukuzumi, S., Kandori, H., Aso, Y. (eds) Chemical Science of π-Electron Systems. Springer, Tokyo. https://doi.org/10.1007/978-4-431-55357-1_1

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