Araştırma Makalesi
BibTex RIS Kaynak Göster

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

Yıl 2016, , 317 - 324, 01.08.2016
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.

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.

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

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

Öz

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. 

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.
Toplam 24 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Konular Mühendislik
Bölüm Araştırma Makalesi
Yazarlar

Erol Asker

Orhan Zeybek

Fahrettin Filiz Bu kişi benim

Yayımlanma Tarihi 1 Ağustos 2016
Gönderilme Tarihi 26 Şubat 2016
Kabul Tarihi 9 Mayıs 2016
Yayımlandığı Sayı Yıl 2016

Kaynak Göster

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. Ağustos 2016;20(2):317-324. doi:10.16984/saufenbilder.70389
Chicago Asker, Erol, Orhan Zeybek, ve 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, sy. 2 (Ağustos 2016): 317-24. https://doi.org/10.16984/saufenbilder.70389.
EndNote Asker E, Zeybek O, Filiz F (01 Ağustos 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, ve 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, c. 20, sy. 2, ss. 317–324, 2016, doi: 10.16984/saufenbilder.70389.
ISNAD Asker, Erol vd. “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 (Ağustos 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 vd. “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, c. 20, sy. 2, 2016, ss. 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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