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

Year 2016, , 317 - 324, 01.08.2016
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.

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.

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

Year 2016, , 317 - 324, 01.08.2016
https://doi.org/10.16984/saufenbilder.70389

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. 

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.
There are 24 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Research Articles
Authors

Erol Asker

Orhan Zeybek

Fahrettin Filiz This is me

Publication Date August 1, 2016
Submission Date February 26, 2016
Acceptance Date May 9, 2016
Published in Issue Year 2016

Cite

APA Asker, E., Zeybek, O., & Filiz, F. (2016). 3,3’-[(E)-eten-1,2-diil]di(9-heksil-9H-karbazol) bileşiğinin sentezi, X-ışını yapı tayini ve teorik yapı tahmini. Sakarya University Journal of Science, 20(2), 317-324. https://doi.org/10.16984/saufenbilder.70389
AMA Asker E, Zeybek O, Filiz F. 3,3’-[(E)-eten-1,2-diil]di(9-heksil-9H-karbazol) bileşiğinin sentezi, X-ışını yapı tayini ve teorik yapı tahmini. SAUJS. August 2016;20(2):317-324. doi:10.16984/saufenbilder.70389
Chicago Asker, Erol, Orhan Zeybek, and Fahrettin Filiz. “3,3’-[(E)-Eten-1,2-diil]di(9-Heksil-9H-Karbazol) bileşiğinin Sentezi, X-ışını Yapı Tayini Ve Teorik Yapı Tahmini”. Sakarya University Journal of Science 20, no. 2 (August 2016): 317-24. https://doi.org/10.16984/saufenbilder.70389.
EndNote Asker E, Zeybek O, Filiz F (August 1, 2016) 3,3’-[(E)-eten-1,2-diil]di(9-heksil-9H-karbazol) bileşiğinin sentezi, X-ışını yapı tayini ve teorik yapı tahmini. Sakarya University Journal of Science 20 2 317–324.
IEEE E. Asker, O. Zeybek, and F. Filiz, “3,3’-[(E)-eten-1,2-diil]di(9-heksil-9H-karbazol) bileşiğinin sentezi, X-ışını yapı tayini ve teorik yapı tahmini”, SAUJS, vol. 20, no. 2, pp. 317–324, 2016, doi: 10.16984/saufenbilder.70389.
ISNAD Asker, Erol et al. “3,3’-[(E)-Eten-1,2-diil]di(9-Heksil-9H-Karbazol) bileşiğinin Sentezi, X-ışını Yapı Tayini Ve Teorik Yapı Tahmini”. Sakarya University Journal of Science 20/2 (August 2016), 317-324. https://doi.org/10.16984/saufenbilder.70389.
JAMA Asker E, Zeybek O, Filiz F. 3,3’-[(E)-eten-1,2-diil]di(9-heksil-9H-karbazol) bileşiğinin sentezi, X-ışını yapı tayini ve teorik yapı tahmini. SAUJS. 2016;20:317–324.
MLA Asker, Erol et al. “3,3’-[(E)-Eten-1,2-diil]di(9-Heksil-9H-Karbazol) bileşiğinin Sentezi, X-ışını Yapı Tayini Ve Teorik Yapı Tahmini”. Sakarya University Journal of Science, vol. 20, no. 2, 2016, pp. 317-24, doi:10.16984/saufenbilder.70389.
Vancouver Asker E, Zeybek O, Filiz F. 3,3’-[(E)-eten-1,2-diil]di(9-heksil-9H-karbazol) bileşiğinin sentezi, X-ışını yapı tayini ve teorik yapı tahmini. SAUJS. 2016;20(2):317-24.

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