Synthesis and Crystal Structure of 4,5,12,13-tetraaza-dibenzo[b,k]chrysene

Famil Valiyev [1]

255 919

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).

 

4, 5, 12, 13-Tetraaza-dibenzo[b, k]chrysene, heterocyclic aromatic hydrocarbons, organic semiconductors, crystal structure
  • (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
Primary Language en
Journal Section Articles
Authors

Author: Famil Valiyev

Dates

Publication Date: December 23, 2015

Bibtex @ { cbayarfbe238087, journal = {Celal Bayar University Journal of Science}, issn = {1305-130X}, eissn = {1305-1385}, address = {Celal Bayar University}, year = {2015}, volume = {11}, pages = {0 - }, doi = {10.18466/cbujos.03944}, title = {Synthesis and Crystal Structure of 4,5,12,13-tetraaza-dibenzo[b,k]chrysene}, key = {cite}, author = {Valiyev, Famil} }
APA Valiyev, F . (2015). Synthesis and Crystal Structure of 4,5,12,13-tetraaza-dibenzo[b,k]chrysene. Celal Bayar University Journal of Science, 11 (3), . Retrieved from http://dergipark.org.tr/cbayarfbe/issue/22162/238087
MLA Valiyev, F . "Synthesis and Crystal Structure of 4,5,12,13-tetraaza-dibenzo[b,k]chrysene". Celal Bayar University Journal of Science 11 (2015): <http://dergipark.org.tr/cbayarfbe/issue/22162/238087>
Chicago Valiyev, F . "Synthesis and Crystal Structure of 4,5,12,13-tetraaza-dibenzo[b,k]chrysene". Celal Bayar University Journal of Science 11 (2015):
RIS TY - JOUR T1 - Synthesis and Crystal Structure of 4,5,12,13-tetraaza-dibenzo[b,k]chrysene AU - Famil Valiyev Y1 - 2015 PY - 2015 N1 - DO - T2 - Celal Bayar University Journal of Science JF - Journal JO - JOR SP - 0 EP - VL - 11 IS - 3 SN - 1305-130X-1305-1385 M3 - UR - Y2 - 2019 ER -
EndNote %0 Celal Bayar University Journal of Science Synthesis and Crystal Structure of 4,5,12,13-tetraaza-dibenzo[b,k]chrysene %A Famil Valiyev %T Synthesis and Crystal Structure of 4,5,12,13-tetraaza-dibenzo[b,k]chrysene %D 2015 %J Celal Bayar University Journal of Science %P 1305-130X-1305-1385 %V 11 %N 3 %R %U
ISNAD Valiyev, Famil . "Synthesis and Crystal Structure of 4,5,12,13-tetraaza-dibenzo[b,k]chrysene". Celal Bayar University Journal of Science 11 / 3 (December 2015): 0-.
AMA Valiyev F . Synthesis and Crystal Structure of 4,5,12,13-tetraaza-dibenzo[b,k]chrysene. Celal Bayar Univ J Sci. 2015; 11(3): 0-.
Vancouver Valiyev F . Synthesis and Crystal Structure of 4,5,12,13-tetraaza-dibenzo[b,k]chrysene. Celal Bayar University Journal of Science. 2015; 11(3): -0.