Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Weir, Ron / Stohner, Jürgen

12 Issues per year


IMPACT FACTOR 2016: 2.626
5-year IMPACT FACTOR: 3.210

CiteScore 2016: 2.45

SCImago Journal Rank (SJR) 2016: 0.972
Source Normalized Impact per Paper (SNIP) 2016: 1.049

Online
ISSN
1365-3075
See all formats and pricing
More options …
Volume 86, Issue 4 (Apr 2014)

Issues

Indenofluorene congeners: Biradicaloids and beyond

Akihiro Shimizu
  • Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Shunpei Nobusue / Hirokazu Miyoshi
  • Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Yoshito Tobe
  • Corresponding author
  • Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2014-03-10 | DOI: https://doi.org/10.1515/pac-2014-5043

Abstract

Singlet biradicaloids are certainly one of the most frequently discussed topics at ISNA-15. In this review our own work on the synthesis, molecular structures, and physical properties relevant to biradical character of indenofluorene isomers are described. These include indeno[2,1-a]fluorene with an o-quinodimethane substructure, benz[c]indeno[2,1-a]fluorene which is the first 2,3-naphthoquinodimethane derivative isolated, and indeno[2,1-b]fluorene with an m-quinodimethane (m-xylylene) subunit. The observed physical properties are explained in terms of the theoretically derived biradical factors (y), HOMO-LUMO energy gaps, and singlet-triplet energy gaps in the ground state electronic configurations. In addition, we discuss here two perspectives in the biradicaloid chemistry, (i) two- and three-dimensional indenofluorene congeners arranged in a macrocyclic form and (ii) macrocyclic indenofluorenes having multiple radical characters.

Keywords: aromatic compounds; ISNA-15; indenofluorenes; quinodimethanes; singlet biradicals

Article note: A collection of invited papers based on presentations at the 15 th International Symposium on Novel Aromatic Compounds (ISNA-15), Taipei, Taiwan, 28 July – 2 August 2013.

References

  • [1]

    (a) T. J. J. Müller, U. H. F. Bunz. Functional Organic Materials, Wiley-VCH, Weinheim, (2007); (b) J. Wu, W. Pisula, K. Müllen. Chem. Rev. 107, 718 (2007); (c) M. Iyoda, J. Yamakawa, M. J. Rahman. Angew. Chem. Int. Ed. 50, 10522 (2011).Google Scholar

  • [2]

    J. Thiele, H. Balhorn. Chem. Ber. 37, 1463 (1904).Google Scholar

  • [3]

    A. E. Tschitschibabin. Chem. Ber. 40, 1810 (1907).Google Scholar

  • [4]

    (a) J. Kolc, J. Michl. J. Am. Chem. Soc. 92, 4147 (1970); (b) J. Kolc, J. Michl. J. Am. Chem. Soc. 95, 7391 (1973).CrossrefGoogle Scholar

  • [5]

    M. Bendikov, H. M. Duong, K. Starkey, K. N. Houk, E. A. Carter, F. Wudl. J. Am. Chem. Soc. 126, 7416 (2004).Google Scholar

  • [6]

    (a) T. Kubo, A. Shimizu, M. Sakamoto, M. Uruichi, K. Yakushi, M. Nakano, D. Shiomi, K. Sato, T. Takui, Y. Morita, K. Nakasuji. Angew. Chem. Int. Ed. 44, 6564 (2005); (b) T. Kubo, A. Shimizu, M. Uruichi, K. Yakushi, M. Nakano, D. Shiomi, K. Sato, T. Takui, M. Morita, K. Nakasuji. Org. Lett. 9, 81 (2007); (c) A. Shimizu, Y. Hirao, M. Matsumoto, H. Kurata, T. Kubo, M. Uruichi, K. Yakushi. Chem. Commun. 48, 5629 (2012).CrossrefGoogle Scholar

  • [7]

    (a) E. Clar, K. F. Lang, H. Sehulz-Kiesow. Chem. Ber. 88, 1520 (1955); (b) R. Umeda, D. Hibi, K. Miki, Y. Tobe. Org. Lett. 11, 4104 (2009); (c) R. Umeda, D. Hibi, K. Miki, Y. Tobe. Pure Appl. Chem. 82, 871 (2010); (d) D. Hibi, K. Kitabayashi, A. Shimizu, R. Umeda, Y. Tobe. Org. Biomol. Chem. accepted, DOI:10.1039/C3OB41674G; (e) T. Wu, C. Chen, D. Hibi, A. Shimizu, Y. Tobe, Y. Wu. Angew. Chem. Int. Ed. 49, 7059 (2010); (f) T. Wu, Y. Wu. Synllet. 0741 (2011); (g) Z. Sun, K. Huang, J. Wu. Org. Lett. 12, 4690 (2010); (h) L. Shan, Z. Liang, X. Xu, Q. Tang, Q. Miao. Chem. Sci. 4, 3294 (2013); (i) Z. Sun, K.-W. Huang, J. Wu. J. Am. Chem. Soc. 133, 11896 (2011); (j) Y. Li, W.-K. Heng, B. S. Lee, N. Aratani, J. L. Zafra, N. Bao, R. Lee, Y. M. Sung, Z. Sun, K.-W. Huang, R. D. Webster, J. T. L. Navarrete, D. Kim, A. Osuka, J. Casado, J. Ding, J. Wu. J. Am. Chem. Soc. 134, 14913 (2012).CrossrefGoogle Scholar

  • [8]

    (a) A. Konishi, Y. Hirao, M. Nakano, A. Shimizu, E. Botek, B. Champagne, D. Shiomi, K. Sato, T. Takui, K. Matsumoto, K. Kurata, T. Kubo. J. Am. Chem. Soc. 132, 11021 (2010); (b) A. Konishi, A. Hirao, K. Matsumoto, H. Kurata, R. Kishi, S. Shigeta, M. Nakano, K. Tokunaga, K. Kamada, T. Kubo. J. Am. Chem. Soc. 135, 1430 (2013).CrossrefGoogle Scholar

  • [9]

    For reviews, see: (a) C. Lambert. Angew. Chem. Int. Ed. 50, 1756 (2011); (b) Z. Sun, J. Wu. J. Mater. Chem. 22, 4151 (2012); (c) Z. Sun, Q. Ye, C. Chi, J. Wu. Chem. Soc. Rev. 41, 7857 (2012); (d) Z. Sun, Z. Zeng, J. Wu. Chem. Asian J. 2013, DOI: 10.1002/asia.201300560.CrossrefGoogle Scholar

  • [10]

    For a review, see: A. G. Fix, D. T. Chase, M. M. Haley. Top. Curr. Chem. DOI: 10.1007/128_2012_376.CrossrefGoogle Scholar

  • [11]

    Q. Zhou, P. J. Carroll, T. M. Swager. J. Org. Chem. 59, 1294 (1994).Google Scholar

  • [12]

    (a) D. T. Chase, B. D. Rose, S. P. McClintock, L. N. Zakharov, M. M. Haley. Angew. Chem. Int. Ed. 50, 1127 (2011); (b) D. T. Chase, A. G. Fix, B. D. Rose, C. D. Weber, S. Nobusue, C. E. Stockwell, L. N. Zakharov, M. C. Lonergan, M. M. Haley. Angew. Chem. Int. Ed. 50, 11103 (2011); (c) D. T. Chase, A. G. Fix, S. J. Kang, B. D. Rose, C. D. Weber, Y. Zhong, L. N. Zakharov, M. C. Lonergan, C. Nuckolls, M. M. Haley. J. Am. Chem. Soc. 134, 10349 (2012); (d) B. D. Rose, C. L. Vonnegut, L. N. Zakharov, M. M. Haley. Org. Lett. 14, 2426 (2012).CrossrefGoogle Scholar

  • [13]

    J. Nishida, S. Tsukaguchi, Y. Yamashita. Chem. Eur. J. 18, 8964 (2012).Google Scholar

  • [14]

    A. G. Fix, P. E. Deal, C. L. Vonnegut, B. D. Rose, L. N. Zakharov, M. M. Haley. Org. Lett. 15, 1362 (2013).Google Scholar

  • [15]

    A. Le Berre. Ann. Chim. 13, 371 (1957).Google Scholar

  • [16]

    A. Shimizu, Y. Tobe. Angew. Chem. Int. Ed. 50, 6906 (2011).Google Scholar

  • [17]

    H. Miyoshi, S. Nobusue, A. Shimizu, I. Hisaki, M. Miyata, Y. Tobe. Chem. Sci. accepted: DOI:10.1039/C3SC52622D.CrossrefGoogle Scholar

  • [18]

    A. Shimizu, R. Kishi, N. Nakano, D. Shiomi, K. Sato, T. Takui, I. Hisaki, M. Miyata. Y. Tobe, Angew. Chem. Int. Ed. 52, 6076 (2013).Google Scholar

  • [19]

    (a) G. Quinkert, W. -W. Wiersdorff, M. Finke, K. Opitz. Tetrahedron Lett. 7, 2193 (1966); (b) G. Quinkert, W. -W. Wiersdorf, M. Finke, K. Opitz, F. -G. von der Haar. Chem. Ber. 101, 2302 (1968).CrossrefGoogle Scholar

  • [20]

    (a) S. Iwashita, E. Ohta, H. Higuchi, H. Kawai, K. Fujiwara, K. Ono, M. Takenaka, T. Suzuki. Chem. Commun. 2076 (2004); (b) T. Suzuki, Y. Sakano, T. Iwai, S. Iwashita, Y. Miura, R. Katoono, H. Kawai, K. Fujiwara, Y. Tsuji, T. Fukushima. Chem. Eur. J. 19, 117 (2013).CrossrefGoogle Scholar

  • [21]

    S. Nobusue, A. Shimizu, K. Hori, I. Hisaki, M. Miyata, Y. Tobe. Angew. Chem. Int. Ed. 52, 4184 (2013).Google Scholar

  • [22]

    (a) M. Gisin, J. Wirz. Helv. Chim. Acta 59, 2273 (1976); (b) R. P. Steiner, R. D. Miller, H. L. Dewey, J. Michl. J. Am. Chem. Soc. 101, 1820 (1979); (c) W. P. Cofino, M. Engelsma, D. A. Kamminga, Ph, G. Hoornweg, C. Gooijer, C. MacLean, N. H. Velthost. Spectrochim. Acta 40A, 269 (1984).Google Scholar

  • [23]

    D. W. Jones, A. Pomfret, R. L. Eife. J. Chem. Soc., Perkin Trans. 1459 (1983).Google Scholar

  • [24]

    (a) B. B. Wright, M. S. Platz. J. Am. Chem. Soc. 105, 628 (1983); (b) P. G. Wenthold , J. B. Kim, W. C. Lineberger. J. Am. Chem. Soc. 119, 1354 (1977).CrossrefGoogle Scholar

  • [25]

    (a) D. Döhnert, J. Koutecký. J. Am. Chem. Soc. 102, 1789 (1980); b) Y. Jung, M. Head-Gordon. ChemPhysChem 4, 522 (2003).Google Scholar

  • [26]

    K. Yamaguchi. Chem. Phys. Lett. 33, 330 (1975).Google Scholar

  • [27]

    T. Uto, T. Nishinaga, A. Matsuura, R. Inoue, K. Komatsu. J. Am. Chem. Soc. 127, 10162 (2005).Google Scholar

  • [28]

    (a) W. E. Barth, R. G. Lawton. J. Am. Chem. Soc. 88, 380 (1966); (b) L. T. Scott, M. M. Hashemi, D. T. Meyers, H. B. Warren. J. Am. Chem. Soc. 113, 7082 (1991); (c) T. J. Seiders, K. K. Baldridge, J. S. Siegel. J. Am. Chem. Soc. 118, 2754 (1996).CrossrefGoogle Scholar

  • [29]

    H. Sakurai, T. Daiko, T. Hirao. Science 301, 1878 (2003).Google Scholar

  • [30]

    For a review: Fragments of Fullerenes and Carbon Nanotubes (M. A. Petrukhina, L. T. Scott, Eds.), John Wiley & Sons, Hoboken (2012).Google Scholar

  • [31]

    D. Hellwinckel, G. Reiff. Angew. Chem. Int. Ed. 9, 527 (1970).Google Scholar

About the article

Corresponding author: Yoshito Tobe, Division of Frontier Materials Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560-8531, Japan, e-mail:


Published Online: 2014-03-10

Published in Print: 2014-04-17


Citation Information: Pure and Applied Chemistry, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1515/pac-2014-5043.

Export Citation

©2014 by IUPAC & De Gruyter Berlin/Boston. Copyright Clearance Center

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

[1]
Soumyajit Das and Jishan Wu
Physical Sciences Reviews, 2017, Volume 2, Number 5
[2]
Xuefeng Lu, Sangsu Lee, Jun Oh Kim, Tullimilli Y. Gopalakrishna, Hoa Phan, Tun Seng Herng, Zhenglong Lim, Zebing Zeng, Jun Ding, Dongho Kim, and Jishan Wu
Journal of the American Chemical Society, 2016, Volume 138, Number 39, Page 13048
[3]
Soumyajit Das, Tun Seng Herng, José L. Zafra, Paula Mayorga Burrezo, Masaaki Kitano, Masatoshi Ishida, Tullimilli Y. Gopalakrishna, Pan Hu, Atsuhiro Osuka, Juan Casado, Jun Ding, David Casanova, and Jishan Wu
Journal of the American Chemical Society, 2016, Volume 138, Number 24, Page 7782
[4]
Jonathan L. Marshall, Nathaniel J. O’Neal, Lev N. Zakharov, and Michael M. Haley
The Journal of Organic Chemistry, 2016, Volume 81, Number 9, Page 3674
[5]
Pan Hu, Sangsu Lee, Kyu Hyung Park, Soumyajit Das, Tun Seng Herng, Théo P. Gonçalves, Kuo-Wei Huang, Jun Ding, Dongho Kim, and Jishan Wu
The Journal of Organic Chemistry, 2016, Volume 81, Number 7, Page 2911
[6]
Akihiro Shimizu, Shunpei Nobusue, Hirokazu Miyoshi, and Yoshito Tobe
ChemInform, 2015, Volume 46, Number 15, Page no

Comments (0)

Please log in or register to comment.
Log in