3,3'-[(E)-eten-1,2-diil]di(9-heksil-9H-karbazol) bileşiğinin sentezi, X-ışını yapı tayini ve teorik yapı tahmini

Erol Asker; Orhan Zeybek; Fahrettin Filiz

doi:10.16984/saufenbilder.70389

Araştırma Makalesi

Synthesis, X-ray structural characterization and theoretical prediction of 3,3'- [(E)-ethene-1,2-diyl]di(9-hexyl-9H-carbazole)

Yıl 2016, Cilt: 20 Sayı: 2, 317 - 324, 01.08.2016

Erol Asker Orhan Zeybek Fahrettin Filiz

https://doi.org/10.16984/saufenbilder.70389

Öz

3,3'-[(E)-ethene-1,2-diyl]di(9-hexyl-9H-carbazole]compound was synthesized in three steps beginning from 9H-carbazole and its structure was characterized via spectroscopic techniques. Its crystal structure was solved in monoclinic space group P2₁/c and geometrical properties were compared with data obtained from PM7 and DFT/B3LYP theoretical calculations. High correlation between DFT computational and X-ray diffraction experimental results has been determined. Intermolecular associations in crystal structure have been attempted to be explained using the calculated frontier orbitals.

Anahtar Kelimeler

crystal structure, DFT and PM7 computations, 1.2-dicarbazolylethene

Kaynakça

D. F. O’Brien, M. A. Baldo, M. E. Thompson, and S. R. Forrest, “Improved energy transfer in electrophosphorescent devices” Appl. Phys. Lett., vol. 74, pp. 442-444, 1999.
S. Grigalevicius, G. Buika, J. V. Grazulevicius, V. Gaidelis, V. Jankauskas, and E. Montrimas, “3,6-Di(diphenylamino)-9-alkylcarbazoles: novel hole-transporting molecular glasses” Synthetic Met., vol. 122, pp. 311-314, 2001.
W. Zhu, M. Hu, R. Yao, and H. Tian, “A novel family of twisted molecular luminescent materials containing carbazole unit for single-layer organic electroluminescent devices” J. Photochem. Photobiol A: Chemistry, vol. 154, pp. 169-177, 2003.
A. Tomkeviciene and J. V. Grazulevicius, “Glass-forming organic semiconductors for optoelectronics” Mater. Sci., vol. 17, pp. 335-342, 2011.
D. E. Lynch, U. Geissler, J. Kwiatkowski, and A. K. Whittaker, “An investigation into the synthesis of polycarbazole squaraine derivatives” Polym. Bull., vol. 38, pp. 493-499, 1997.
Bruker (2012). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
R. H. Blessing, "An empirical correction for absorption anisotropy" Acta Crystallogr., vol. A 51.1, pp. 33-38, 1995.
A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, "SIR92, Altomare. "program for crystal structure solution" J. Appl. Crystallogr., vol. 26, pp. 343, 1993.
G. M. Sheldrick, “A short history of SHELX” Acta Crystallogr. A, vol. A64, pp. 112-122, 2008.
L. J. Farrugia, "WinGX and ORTEP for Windows: an update" J. Appl. Crystallogr., vol. 45.4, pp. 849-854, 2012.
C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, P. A. Wood, "Mercury CSD 2.0–new features for the visualization and investigation of crystal structures" J. Appl. Crystallogr., vol. 41.2, pp. 466-470, 2008.
L. J. Farrugia, "WinGX and ORTEP for Windows: an update" J. Appl. Crystallogr., vol. 45.4, pp. 849-854, 2012.
M. D. Hanwell, D. E. Curtis, D. C. Lonie, T. Vandermeersch, E. Zurek, G. R. Hutchison, "Avogadro: An advanced semantic chemical editor, visualization, and analysis platform" J. Cheminformatics, vol. 4.1, pp. 17, 2012.
A. D. Becke, "Density-functional exchange-energy approximation with correct asymptotic behavior" Phys. rev. A, vol. 38.6, pp. 3098-3100, 1988.
A. D. Becke, "Density‐functional thermochemistry. I. The effect of the exchange‐only gradient correction" J. chem. phys., vol. 96.3, pp. 2155-2160, 1992.
C. Lee, W. Yang, R. G. Parr, "Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density" Phys. rev. B, vol. 37.2, pp. 785, 1988.
M. S. Gordon, W. S. Michael. "Advances in Electronic Structure Theory: Gamess A Decade Later" (2005).
M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, "General atomic and molecular electronic structure system" J. Comput. Chem., vol. 14.11, pp. 1347-1363, 1993.
W. Humphrey, A. Dalke, K. Schulten. "VMD: visual molecular dynamics" J. mol. graphics, vol. 14.1, pp. 33-38, 1996.
C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler, J. van de Streek, J. V. D. "Mercury: visualization and analysis of crystal structures" J. Appl. Crystallogr., 39(3), 453-457, 2006.
E. Asker, J. Masnovi, “1,3-Bis(9-ethylcarbazol-3-yl)propane,” Acta Cryst. E, vol. E61, pp. o2781-o2783, 2005.
E. Asker, F. Filiz, “Synthesis and charge-transfer complex formations of 1,n-bis(3,6-diethylcarbazol-9-yl)alkanes with three π-acceptors” J. Mol. Struct., vol. pp. 65-74, 2013.
K. Fukui, Theory of orientation and stereoselection. Vol. 2. Springer Science & Business Media, pp. 40, 2013.
Y. Shirota, "Photo-and electroactive amorphous molecular materials-molecular design, syntheses, reactions, properties, and applications" J. Mater. Chem., vol. 15.1 75-93, 2005.