Syntheses, Characterization and DFT Analysis of Two Novel Thiaheterohelicene DerivativesReport as inadecuate




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Two novel thiaheterohelicene derivatives were synthesized from the corresponding 2,2-2,6-naphthalenediyl-di-2,1-ethenediyl bis-thiophene and its dimethyl substituted analogue 2,2-2,6-naphthalenediyldi-2,1-ethenediyl bis-2’’-methylthiophene using oxidative photo cyclization reaction. The compounds were characterized by 1H NMR, electron impact-mass spectrometry, elemental analyses, and the absolute molecular structures were determined by single crystal X-ray diffraction analysis. They crystallized under monoclinic system with space group P21-n for the unsubstituted compound and P21-c for the methyl substituted compound, respectively. The dihedral angle between the terminal thiophene ring and the molecular center was observed to be 20.82? for the methyl substituted compound, respectively. Furthermore, molecules oriented as herringbone structures by intermolecular π-π stacking in the crystals. The relative study of the actual arrangement of these molecules has been carried out using X-ray diffraction analysis. The two molecules have different crystal packing. The molecule 3b has herring bone like arrangement due to the substituent bulkiness and weak CH-π interaction. On the other hand, the molecular packing of molecule 3a is not herringbone probably due to the multiple weak intermolecular CH-S short contacts between columns consisting of stacked molecules.

KEYWORDS

Crystal Structure, Thiaheterohelicene Derivative, Strained Structure, Single Crystal X-Ray Study

Cite this paper

Moriguchi, T. , Mitsumoto, K. , Nishizawa, Y. , Yakeya, D. , Jalli, V. and Tsuge, A. 2016 Syntheses, Characterization and DFT Analysis of Two Novel Thiaheterohelicene Derivatives. Crystal Structure Theory and Applications, 5, 63-73. doi: 10.4236-csta.2016.54006.





Author: Tetsuji Moriguchi*, Keiichi Mitsumoto, Yuki Nishizawa, Daisuke Yakeya, Venkataprasad Jalli, Akihiko Tsuge

Source: http://www.scirp.org/



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