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

Year 2016, Volume: 20 Issue: 2, 317 - 324, 01.08.2016

Erol Asker Orhan Zeybek Fahrettin Filiz

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

Abstract

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.

Keywords

crystal structure, DFT and PM7 computations, 1.2-dicarbazolylethene

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

Abstract

3,3'-[(E)-eten-1,2-diil]di(9-heksil-9H-karbazol) bileşiği 9H-karbazoldan çıkarak üç basamakta sentezlenmiş ve yapısı spektroskopik yöntemlerle aydınlatılmıştır. Kristal yapısı monoklinik uzay grubu P2₁/c'de çözülmüş ve geometrik özellikleri yarı-deneysel PM7 ve teorik DFT/B3LYP hesaplamalarla elde edilen verilerle karşılaştırılmıştır. DFT hesapsal sonuçlar ile X-ışını kırınımı deneysel sonuçlar arasında yüksek korelasyon belirlenmiştir. Kristal yapıdaki moleküller arası etkileşimler hesaplanan öncü orbitallerle açıklanmaya çalışılmıştır. 

Keywords

1.2-dikarbazolileten, kristal yapı, DFT ve PM7 hesaplamaları

References

• 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.