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Year 2015, Volume: 11 Issue: 3, 339 - 344, 23.12.2015
https://doi.org/10.18466/cbujos.03944

Abstract

References

  • (a) Moon, H.; Zeis, R.; Borkent, E. J.; Besnard, C.; Lovinger, A. J.; Siegrist, T.; Kloc, C.; Bao, Z. J. Am. Chem.Soc. 2004, 126, 15322. (b) Murphy, A. R.; Frechet, J. M. J. Chem. Rev. 2007, 107, 1066. (c) Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99. (d) Muccini, M. Nat. Mater. 2006, 5, 605. (e) Schön, J. H.; Berg S.; Kloc, C.; Batlogg, B. Science 2000, 287, 1022. (f) Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891.
  • (a) Klauk, H.; Halik, M.; Zschieschang, U.; Schmid, G.; Radlik, W.; Weber, W. J. Appl. Phys. 2002, 92, 5259. (b) Kelley, T. W.; Boardman, L. D.; Dunbar, T. D.; Muyres, D. V.; Pellerites, M. J.; Smith, T. P. J. Phys. Chem. B 2003, 107, 5877. (c) Lin, Y. Y.; Gundlach, D. J.; Nelson, S. F.; Jackson, T. N. IEEE Electron Device Lett. 1997, 18, 606. (d) Klauk, H.; Gundlach, D. J.; Nichols, J. A.; Jackson, T. N. IEEE Trans. Electron. Devices 1999, 46, 1258.
  • (a) Katz, H. E.; Z; Bao, Z; Gilat, S. L. Acc. Chem. Res. 2001, 34, 359. (b) Laquindanum, J. G.; Katz, H. E.; Lovinger, A. J. J. Am. Chem. Soc. 1998, 120, 664. (c) Herwig, P. T.; Mullen, K. Adv. Mater. 1999, 11, 480.
  • (a) Holmes, D.; Kumaraswamy, S.; Matzger, A. J.; Vollhardt, K. P. C. Chem. Eur. J. 1999, 5, 3399. (b) Bredas, J. L.; Calbert, J. P.; da Silva Filho, D. A.; Cornil, J. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5804.
  • (a) Stassen, A. F.; de Boer, R. W. I.; Iosad, N. N. Appl. Phys. Lett. 2004, 85, 3899. (b) Reese, C.; Bao, Z. J. Mater. Chem. 2006, 16, 329 (c) de Boer, R. W. I.; Gershenson, M. E.; Morpurgo, A. F. Phys. Stat. Sol. (a) 2004, 201, 1302.
  • (a) Hasegawa, T.; Mattenberger, K.; Takeya, J.; Batologg, B. Phys. Rev. 2004, B 69, 245115. (b) Takeya, J.; Goldmann, C.; Haas, S.; Pernstich, K. P.; Ketterer, B.; Batlogg, B. J. Appl. Phys. 2003, 94, 5800. (c) De Boer, R. W. I.; Klapwijk, T. M.; Morpurgo, A. M. Appl. Phys. Lett. 2003, 83, 4345.
  • (a) Sundar, V. C.; Zaumseil, J.; Podzorov, V.; Menard, E.; Willett, R. L.; Someya, T.; Gershenson, M. E.; Rogers, J. A. Science 2004, 303, 1644. (b) Podzorov, V.; Menard, E.; Borissov, A.; Kiryukhin, V.; Rogers, J. A.; Gershenson, M. E. Phys. Rev. Lett. 2004, 93, 086602.
  • Bre´das, J. L.; Calbert, J. P.; da Silva, D. A.; Cornil. J. Proc. Natl. Acad. Sci. 2002, 99, 5804-5809.
  • Cornil, J.; Beljonne, D.; Calbert, J. P.; Bre´das, J. L. AdV. Mater. 2001, 13, 1053-1067.
  • Curtis, M. D.; Cao, J.; Kampf, J. W. J. Am. Chem. Soc. 2004, 126, 4318-4328.
  • Li, X. C.; Sirringhaus, H.; Garnier, F.; Holmes, A. B.; Moratti, S. C.; Feeder, N.; Clegg, W.; Teat, S. J.; Friend, R. H. J. Am. Chem. Soc. 1998, 120, 2206.
  • Zhang, X.; Cote, A. P.; Matzger, A. J. J. Am. Chem. Soc. 2005, 127, 10502.
  • Anthony, J. E.; Brooks, J. S.; Eaton, D. L.; Parkin, S. R. J. Am. Chem. Soc. 2001, 123, 9482.
  • Yoon, M. H.; Facchetti, A.; Stern, C. E.; Marks, T. J. J. Am. Chem. Soc. 2006, 128, 5792.
  • Ando, S.; Murakami, R.; Nishida, J.; Tada, H.; Inoue, Y.; Tokito, S., Yamashita, Y. J. Am. Chem. Soc. 2005, 127, 14996.
  • M. Islam, F.Valiyev, Hsiu-Feng Lu,Ming-Yu Kuo,Y.T.Tao, Chem. Commun., 2011, 47, 2008–2010

Synthesis and Crystal Structure of 4,5,12,13Tetraaza-Dibenzo[b,k]Chrysene

Year 2015, Volume: 11 Issue: 3, 339 - 344, 23.12.2015
https://doi.org/10.18466/cbujos.03944

Abstract

New synthetic methodology of fused aromatic hydrocarbons with nitrogen heterocyclic of 4,5,12,13-Tetraaza-dibenzo[b,k]chrysene(4) were designed and synthesized by chemical methods. Compound 4 fully characterized by 1H NMR, 13C NMR, EI-mass spectral, elemental and single crystal X-ray analysis. Molecules of 4 are completely planar and form face-to-face π-stacking. Shortest distances between fused rings of π- π interactions are 3.346 Å. Compound (4) is a potential candidate for high mobility single crystal organic field effect transistors (OFET’s).

 

References

  • (a) Moon, H.; Zeis, R.; Borkent, E. J.; Besnard, C.; Lovinger, A. J.; Siegrist, T.; Kloc, C.; Bao, Z. J. Am. Chem.Soc. 2004, 126, 15322. (b) Murphy, A. R.; Frechet, J. M. J. Chem. Rev. 2007, 107, 1066. (c) Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99. (d) Muccini, M. Nat. Mater. 2006, 5, 605. (e) Schön, J. H.; Berg S.; Kloc, C.; Batlogg, B. Science 2000, 287, 1022. (f) Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891.
  • (a) Klauk, H.; Halik, M.; Zschieschang, U.; Schmid, G.; Radlik, W.; Weber, W. J. Appl. Phys. 2002, 92, 5259. (b) Kelley, T. W.; Boardman, L. D.; Dunbar, T. D.; Muyres, D. V.; Pellerites, M. J.; Smith, T. P. J. Phys. Chem. B 2003, 107, 5877. (c) Lin, Y. Y.; Gundlach, D. J.; Nelson, S. F.; Jackson, T. N. IEEE Electron Device Lett. 1997, 18, 606. (d) Klauk, H.; Gundlach, D. J.; Nichols, J. A.; Jackson, T. N. IEEE Trans. Electron. Devices 1999, 46, 1258.
  • (a) Katz, H. E.; Z; Bao, Z; Gilat, S. L. Acc. Chem. Res. 2001, 34, 359. (b) Laquindanum, J. G.; Katz, H. E.; Lovinger, A. J. J. Am. Chem. Soc. 1998, 120, 664. (c) Herwig, P. T.; Mullen, K. Adv. Mater. 1999, 11, 480.
  • (a) Holmes, D.; Kumaraswamy, S.; Matzger, A. J.; Vollhardt, K. P. C. Chem. Eur. J. 1999, 5, 3399. (b) Bredas, J. L.; Calbert, J. P.; da Silva Filho, D. A.; Cornil, J. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5804.
  • (a) Stassen, A. F.; de Boer, R. W. I.; Iosad, N. N. Appl. Phys. Lett. 2004, 85, 3899. (b) Reese, C.; Bao, Z. J. Mater. Chem. 2006, 16, 329 (c) de Boer, R. W. I.; Gershenson, M. E.; Morpurgo, A. F. Phys. Stat. Sol. (a) 2004, 201, 1302.
  • (a) Hasegawa, T.; Mattenberger, K.; Takeya, J.; Batologg, B. Phys. Rev. 2004, B 69, 245115. (b) Takeya, J.; Goldmann, C.; Haas, S.; Pernstich, K. P.; Ketterer, B.; Batlogg, B. J. Appl. Phys. 2003, 94, 5800. (c) De Boer, R. W. I.; Klapwijk, T. M.; Morpurgo, A. M. Appl. Phys. Lett. 2003, 83, 4345.
  • (a) Sundar, V. C.; Zaumseil, J.; Podzorov, V.; Menard, E.; Willett, R. L.; Someya, T.; Gershenson, M. E.; Rogers, J. A. Science 2004, 303, 1644. (b) Podzorov, V.; Menard, E.; Borissov, A.; Kiryukhin, V.; Rogers, J. A.; Gershenson, M. E. Phys. Rev. Lett. 2004, 93, 086602.
  • Bre´das, J. L.; Calbert, J. P.; da Silva, D. A.; Cornil. J. Proc. Natl. Acad. Sci. 2002, 99, 5804-5809.
  • Cornil, J.; Beljonne, D.; Calbert, J. P.; Bre´das, J. L. AdV. Mater. 2001, 13, 1053-1067.
  • Curtis, M. D.; Cao, J.; Kampf, J. W. J. Am. Chem. Soc. 2004, 126, 4318-4328.
  • Li, X. C.; Sirringhaus, H.; Garnier, F.; Holmes, A. B.; Moratti, S. C.; Feeder, N.; Clegg, W.; Teat, S. J.; Friend, R. H. J. Am. Chem. Soc. 1998, 120, 2206.
  • Zhang, X.; Cote, A. P.; Matzger, A. J. J. Am. Chem. Soc. 2005, 127, 10502.
  • Anthony, J. E.; Brooks, J. S.; Eaton, D. L.; Parkin, S. R. J. Am. Chem. Soc. 2001, 123, 9482.
  • Yoon, M. H.; Facchetti, A.; Stern, C. E.; Marks, T. J. J. Am. Chem. Soc. 2006, 128, 5792.
  • Ando, S.; Murakami, R.; Nishida, J.; Tada, H.; Inoue, Y.; Tokito, S., Yamashita, Y. J. Am. Chem. Soc. 2005, 127, 14996.
  • M. Islam, F.Valiyev, Hsiu-Feng Lu,Ming-Yu Kuo,Y.T.Tao, Chem. Commun., 2011, 47, 2008–2010
There are 16 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Famil Valiyev This is me

Publication Date December 23, 2015
Published in Issue Year 2015 Volume: 11 Issue: 3

Cite

APA Valiyev, F. (2015). Synthesis and Crystal Structure of 4,5,12,13Tetraaza-Dibenzo[b,k]Chrysene. Celal Bayar Üniversitesi Fen Bilimleri Dergisi, 11(3), 339-344. https://doi.org/10.18466/cbujos.03944
AMA Valiyev F. Synthesis and Crystal Structure of 4,5,12,13Tetraaza-Dibenzo[b,k]Chrysene. CBUJOS. December 2015;11(3):339-344. doi:10.18466/cbujos.03944
Chicago Valiyev, Famil. “Synthesis and Crystal Structure of 4,5,12,13Tetraaza-Dibenzo[b,k]Chrysene”. Celal Bayar Üniversitesi Fen Bilimleri Dergisi 11, no. 3 (December 2015): 339-44. https://doi.org/10.18466/cbujos.03944.
EndNote Valiyev F (December 1, 2015) Synthesis and Crystal Structure of 4,5,12,13Tetraaza-Dibenzo[b,k]Chrysene. Celal Bayar Üniversitesi Fen Bilimleri Dergisi 11 3 339–344.
IEEE F. Valiyev, “Synthesis and Crystal Structure of 4,5,12,13Tetraaza-Dibenzo[b,k]Chrysene”, CBUJOS, vol. 11, no. 3, pp. 339–344, 2015, doi: 10.18466/cbujos.03944.
ISNAD Valiyev, Famil. “Synthesis and Crystal Structure of 4,5,12,13Tetraaza-Dibenzo[b,k]Chrysene”. Celal Bayar Üniversitesi Fen Bilimleri Dergisi 11/3 (December 2015), 339-344. https://doi.org/10.18466/cbujos.03944.
JAMA Valiyev F. Synthesis and Crystal Structure of 4,5,12,13Tetraaza-Dibenzo[b,k]Chrysene. CBUJOS. 2015;11:339–344.
MLA Valiyev, Famil. “Synthesis and Crystal Structure of 4,5,12,13Tetraaza-Dibenzo[b,k]Chrysene”. Celal Bayar Üniversitesi Fen Bilimleri Dergisi, vol. 11, no. 3, 2015, pp. 339-44, doi:10.18466/cbujos.03944.
Vancouver Valiyev F. Synthesis and Crystal Structure of 4,5,12,13Tetraaza-Dibenzo[b,k]Chrysene. CBUJOS. 2015;11(3):339-44.