Syntheses, Characterization and DFT Analysis of Two Novel Thiaheterohelicene Derivatives

Tetsuji  Moriguchi; Keiichi  Mitsumoto; Yuki  Nishizawa; Daisuke  Yakeya; Venkataprasad  Jalli; Akihiko  Tsuge

doi:10.4236/csta.2016.54006

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

Abstract: 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 P2_1/n for the unsubstituted compound and P2_1/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 unsubstituted compound and 14.27? 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.

References

[1] Storch, J., Zadny, J., Strasak, T., Kubala, M., Sykora, J., Dusek, M., Cirkva, V., Matejka, P., Krbal, M. and Vacek, J. (2015) Synthesis and Characterization of a Helicene-Based Imidazolium Salt and Its Application in Organic Molecular Electronics. Chemistry—A European Journal, 21, 2343-2347.
https://doi.org/10.1002/chem.201405239

[2] Field, J.E., Muller, G., Riehl, J.P. and Venkataraman, D. (2003) Circularly Polarized Luminescence from Bridged Triarylamine Helicenes. Journal of the American Chemical Society, 125, 11808-11809.
https://doi.org/10.1021/ja035626e

[3] Nuckolls, C., Shao, R., Jang, W.G., Clark, N.A., Walba, D.M. and Katz, T.J. (2002) Electro-Optic Switching by Helicene Liquid Crystals. Chemistry of Materials, 14, 773-776.
https://doi.org/10.1021/cm010628o

[4] Nuckolls, C. and Katz, T.J. (1998) Synthesis, Structure, and Properties of a Helical Columnar Liquid Crystal. Journal of the American Chemical Society, 120, 9541-9544.
https://doi.org/10.1021/ja982025s

[5] Wang, D.W. and Katz, T.J. (2005) A [5]HELOL Analogue That Senses Remote Chirality in Alcohols, Phenols, Amines and Carboxylic Acids. The Journal of Organic Chemistry, 70, 8497-8502.
https://doi.org/10.1021/jo0512913

[6] Nuckolls, C., Katz, T.J., Verbiest, T., Elshocht, S.V., Kuball, H.G., Kiesewalter, S., Lovinger, A.J. and Persoons, A. (1998) Circular Dichroism and UV-Visible Absorption Spectra of the Langmuir-Blodgett Films of an Aggregating Helicene. Journal of the American Chemical Society, 120, 8656-8660.
https://doi.org/10.1021/ja981757h

[7] Yamamoto, K., Ikeda, T., Kitsuki, T., Okamoto, Y., Chikamatsu, H. and Nakazaki, M. (1990) Synthesis and Chiral Recognition of Optically Active Crown Ethers Incorporating a Helicene Moiety as the Chiral Centre. Journal of the Chemical Society, Perkin Transactions., 1, 271-276.
https://doi.org/10.1039/p19900000271

[8] Tsuji, H., Mitsui, C., Ilies, L., Sato, Y. and Nakamura, E. (2007) Synthesis and Properties of 2,3,6,7-Tetraarylbenzo[1,2-b:4,5-b’]difurans as Hole-Transporting Material. Journal of the American Chemical Society, 129, 11902-11903.
https://doi.org/10.1021/ja074365w

[9] Mitsui, C., Soeda, J., Miwa, K., Tsuji, H., Takeya, J. and Nakamura, E. (2012) Naphtho[2,1-b:6,5-b’]difuran: A Versatile Motif Available for Solution-Processed Single-Crystal Organic Field-Effect Transistors with High Hole Mobility. Journal of the American Chemical Society, 134, 5448-5451.
https://doi.org/10.1021/ja2120635

[10] Nakano, M., Niimi, K., Miyazaki, E., Osaka, I. and Takimiya, K. (2012) Isomerically Pure Anthra[2,3-b:6,7-b’]-difuran (anti-ADF), -dithiophene (anti-ADT), and -diselenophene (anti-ADS): Selective Synthesis, Electronic Structures, and Application to Organic Field-Effect Transistors. The Journal of Organic Chemistry, 77, 8099-8111.
https://doi.org/10.1021/jo301438t

[11] Wu, J.-S., Lin, C.-T., Wang, C.-L., Cheng, Y.-J. and Hsu, C.-S. (2012) New Angular-Shaped and Isomerically Pure Anthradithiophene with Lateral Aliphatic Side Chains for Conjugated Polymers: Synthesis, Characterization, and Implications for Solution-Prossessed Organic Field-Effect Transistors and Photovoltaics. Chemistry of Materials, 24, 2391-2399.
https://doi.org/10.1021/cm301176s

[12] Areephong, J., Ruangsupapichart, N. and Thongpanchang, T. (2004) Enantioselective Bioreduction of Ethyl 4,4,4-Trihalide-3-oxobutanoate by Kluyveromyces marxianus. Tetrahedron Letters, 45, 3067-3070.
https://doi.org/10.1016/j.tetlet.2004.02.105

[13] Salim, M., Akutsu, A., Kimura, T., Minabe, M. and Karikomi, M. (2011) Novel Synthesis of Oxa[9]helicenes by Lawesson’s Reagent-Mediated Cyclization of Helical Quinone Derivatives. Tetrahedron Letters, 52, 4518-4520.
https://doi.org/10.1016/j.tetlet.2011.06.033

[14] Irie, R., Tanoue, A., Urakawa, S., Imahori, T., Igawa, K., Matsumoto, T., Tomooka, K., Kikuta, S., Uchida, T. and Katsuki, T. (2011) Synthesis and Stereochemical Behavior of a New Chiral Oxa[7]heterohelicene. Chemistry Letters, 40, 1343-1345.
https://doi.org/10.1246/cl.2011.1343

[15] Roncali, J. (1992) Conjugated Poly(thiophenes): Synthesis, Functionalization, and Applications. Chemical Reviews, 92, 711-738.
https://doi.org/10.1021/cr00012a009

[16] Roncali, J. (1997) Synthetic Principles for Bandgap Control in Linear π-Conjugated Systems. Chemical Reviews, 97, 173-206.
https://doi.org/10.1021/cr950257t

[17] Yamamoto, T., Arai, M., Kokubo, H. and Sasaki, S. (2003) Copolymers of Thiophene and Thiazole. Regioregulation in Synthesis, Stacking Structure, and Optical Properties. Macromolecules, 36, 7986-7993.
https://doi.org/10.1021/ma030167n

[18] Yamamoto, T., Komarudin, D., Arai, M., Lee, B.-L., Suganuma, H., Asakawa, N., Inoue, Y., Kubota, K., Sasaki, S., Fukuda, T. and Matsuda, H. (1998) Extensive Studies on π-Stacking of Poly(3-alkylthiophene-2,5-diyl)s and Poly(4-alkylthiazole-2,5-diyl)s by Optical Spectroscopy, NMR Analysis, Light Scattering Analysis, and X-Ray Crystallography. Journal of the American Chemical Society, 120, 2047-2058.
https://doi.org/10.1021/ja973873a

[19] Katayama, T., Nakatsuka, S., Hirai, H., Yasuda, N., Kumar, J., Kawai, T. and Hatakeyama, T. (2016) Two-Step Synthesis of Boron-Fused Double Helicenes. Journal of the American Chemical Society, 138, 5210-5213.
https://doi.org/10.1021/jacs.6b01674

[20] Bruker AXS Inc. (2009) APEX2 Version 2009.9.

[21] Bruker AXS Inc. (2009) SAINT Version 7.68A.

[22] Sheldrick, G.M. (2008) XPREP Version 2008/2. Bruker AXS Inc., Madison.

[23] Sheldrick, G.M. (2008) SADABS, Version 2008/1. Bruker AXS Inc., Madison.

[24] Sheldrick, G.M. (2008) SHELX Version 2014/6. Acta Crystallographica, A64, 112-122.
https://doi.org/10.1107/S0108767307043930

[25] Halgren, T.A. (1996) Merck Molecular Force Field. I. Basis, Form, Scope, Parameterization, and Performance of MMFF94. Journal of Computational Chemistry, 17, 490-519.
https://doi.org/10.1002/(SICI)1096-987X(199604)17:5/6<490::AID-JCC1>3.0.CO;2-P