Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
2-D Columnar Assemblies of Diblock Rod-Coil Molecules Incorporating Cholesteryl Group
Corresponding Author(s) : Tie Chen
Asian Journal of Chemistry,
Vol. 26 No. 4 (2014): Vol 26 Issue 4
Abstract
Rod-coil molecules have a strong tendency to self-organize into supra-molecular nanostructures in the bulk state. In this article, we report synthesis and self-assembling behaviour of rod-coil molecules 1-3, consisting of a biphenyl and cholesteryl group as a rod segment and poly(ethylene oxide) (PEO) with a degree of polymerization of 7, 12 and 17 coil segments. Self-organization behaviour of these molecules investigated by means of differential scanning calorimetry, thermal polarizing optical microscopy and small-angle X-ray scattering in the bulk state reveal that volume fraction of PEO coil segments containing alkyl chain of cholesteryl group dramatically influence the self assembling behaviour of rod building block in the liquid crystalline phase. Molecules 1-3 self-assemble into 1-D bilayered structures with different d-spacing according to the lengths of coil domains in the solid state. While, self-organized molecular structures transfer into oblique columnar structure for molecule 1 and 2 from the crystalline to the liquid crystalline phase, further increasing coil to rod volume fraction, molecule 3 self assemble into hexagonal columnar aggregate through p-p stacking of rod building blocks.
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- A. Ajayaghosh, R. Varghese, S.J. George and C. Vijayakumar, Angew. Chem. Int. Ed., 45, 1141 (2006); doi:10.1002/anie.200503142.
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- V. Percec, J.G. Rudick, M. Peterca and P.A. Heiney, J. Am. Chem. Soc., 130, 7503 (2008); doi:10.1021/ja801863e.
- J. Lee, J. Kim, M. Yun, C. Park, J. Park, K.-H. Lee and C. Kim, Soft Matter, 7, 7503 (2011).
- H.-J. Kim, T. Kim and M. Lee, Acc. Chem. Res., 44, 72 (2011); doi:10.1021/ar100111n.
- L. Liu, D.-J. Hong and M. Lee, Langmuir, 25, 5061 (2009); doi:10.1021/la804043z.D.-J. HongM. Lee
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- K.L. Zhong, T. Chen, B.Z. Yin and L.Y. Jin, Macromol. Res., 17, 280 (2009); doi:10.1007/BF03218693.
- L. Chen, K.L. Zhong, L.Y. Jin, Z.G. Huang, L. Liu and L.S. Hirst, Macromol. Res., 18, 800 (2010); doi:10.1007/s13233-010-0812-6.
- C.C. Yang, K.L. Zhong, Q. Wang, T. Chen and L.Y. Jin, Fibers Polymers, 12, 983 (2011); doi:10.1007/s12221-011-0983-6.
- K.- Zhong, Z. Man, Z. Huang, T. Chen, B. Yin and L. Yi Jin, Polym. Int., 60, 845 (2011); doi:10.1002/pi.3030.
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- H. Cho, L. Widanapathirana and Y. Zhao, J. Am. Chem. Soc., 133, 141 (2011); doi:10.1021/ja109036z.
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- S. Trachtenberg and R. Gilad, Mol. Microbiol., 41, 827 (2001); doi:10.1046/j.1365-2958.2001.02527.x.
- A.H. Kycia, J. Wang, A.R. Merrill and J. Lipkowski, Langmuir, 27, 10867 (2011); doi:10.1021/la2016269.
References
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W. Jin, T. Fukushima, A. Kosaka, M. Niki, N. Ishii and T. Aida, J. Am. Chem. Soc., 127, 8284 (2005); doi:10.1021/ja051859p.
H.S. Jeong, Y.H. Kim, J.S. Lee, J.H. Kim, M. Srinivasarao and H.-T. Jung, Adv. Mater., 24, 381 (2012); doi:10.1002/adma.201103817.
V. Percec, J.G. Rudick, M. Peterca and P.A. Heiney, J. Am. Chem. Soc., 130, 7503 (2008); doi:10.1021/ja801863e.
J. Lee, J. Kim, M. Yun, C. Park, J. Park, K.-H. Lee and C. Kim, Soft Matter, 7, 7503 (2011).
H.-J. Kim, T. Kim and M. Lee, Acc. Chem. Res., 44, 72 (2011); doi:10.1021/ar100111n.
L. Liu, D.-J. Hong and M. Lee, Langmuir, 25, 5061 (2009); doi:10.1021/la804043z.D.-J. HongM. Lee
D.G.D. Patel, F. Feng, Y.- Ohnishi, K.A. Abboud, S. Hirata, K.S. Schanze and J.R. Reynolds, J. Am. Chem. Soc., 134, 2599 (2012); doi:10.1021/ja207978v.
T.L.D. Tam, W. Ye, H.H.R. Tan, F. Zhou, H. Su, S.G. Mhaisalkar and A.C. Grimsdale, J. Org. Chem., 77, 10035 (2012); doi:10.1021/jo301281d.
F.J.M. Hoeben, P. Jonkheijm, E.W. Meijer and A.P.H.J. Schenning, Chem. Rev., 105, 1491 (2005); doi:10.1021/cr030070z.
L.Y. Jin, J. Bae, J.H. Ryu and M. Lee, Angew. Chem. Int. Ed., 45, 650 (2006); doi:10.1002/anie.200502911.
K.L. Zhong, Z. Huang, Z. Man, L.Y. Jin, B. Yin and M. Lee, J. Polym. Sci. A, Polym. Chem., 48, 1415 (2010); doi:10.1002/pola.23909.
L. Yi Jin, J. Bae, J.-H. Ahn and M. Lee, Chem. Commun., 1197 (2005); doi:10.1039/b416089d.
B.K. Cho, M. Lee, N.K. Oh and W.C. Zin, J. Am. Chem. Soc., 123, 9677 (2001); doi:10.1021/ja011313c.
H.A. Klok, J.F. Langenwalter and S. Lecommandoux, Macromolecules, 33, 7819 (2000); doi:10.1021/ma0009606.
E. Lee, Z. Huang, J. Ryu and M. Lee, Chem. Eur. J., 14, 6957 (2008); doi:10.1002/chem.200800664.
K.L. Zhong, C.C. Yang, T. Chen, B.Z. Yin, L.Y. Jin, Z. Huang and E. Lee, Macromol. Res., 18, 289 (2010); doi:10.1007/s13233-010-0313-7.
C.-H. Choi, J.-H. Lee, T.-S. Hwang, C.-S. Lee, Y.-G. Kim, Y.-H. Yang and K.M. Huh, Macromol. Res., 18, 254 (2010); doi:10.1007/s13233-010-0314-6.
A. Ghosh and W.B. Lee, Macromol. Res., 19, 483 (2011); doi:10.1007/s13233-011-0510-z.
L.Y. Jin, R. Hou, T. Chen, M. Fang, S. Mah and B. Yin, Fibers Polymers, 8, 143 (2007); doi:10.1007/BF02875783.
K.L. Zhong, T. Chen, B.Z. Yin and L.Y. Jin, Macromol. Res., 17, 280 (2009); doi:10.1007/BF03218693.
L. Chen, K.L. Zhong, L.Y. Jin, Z.G. Huang, L. Liu and L.S. Hirst, Macromol. Res., 18, 800 (2010); doi:10.1007/s13233-010-0812-6.
C.C. Yang, K.L. Zhong, Q. Wang, T. Chen and L.Y. Jin, Fibers Polymers, 12, 983 (2011); doi:10.1007/s12221-011-0983-6.
K.- Zhong, Z. Man, Z. Huang, T. Chen, B. Yin and L. Yi Jin, Polym. Int., 60, 845 (2011); doi:10.1002/pi.3030.
H.A. Klok, J.J. Hwang, J.D. Hartgerink and S.I. Stupp, Macromolecules, 35, 6101 (2002); doi:10.1021/ma011964t.
P. Xue, R. Lu, G. Chen, Y. Zhang, H. Nomoto, M. Takafuji and H. Ihara, Chem. Eur. J., 13, 8231 (2007); doi:10.1002/chem.200700321.
H. Cho, L. Widanapathirana and Y. Zhao, J. Am. Chem. Soc., 133, 141 (2011); doi:10.1021/ja109036z.
M.F. Ottaviani, M. Cangiotti, L. Fiorani, A. Barnard, S.P. Jones and D.K. Smith, New J. Chem., 36, 469 (2012); doi:10.1039/c1nj20685k.
S. Tomas and L. Milanesi, J. Am. Chem. Soc., 131, 6618 (2009); doi:10.1021/ja900561j.
M. Banchelli, F. Betti, D. Berti, G. Caminati, F.B. Bombelli, T. Brown, L.M. Wilhelmsson, B. Nordén and P. Baglioni, J. Phys. Chem. B, 112, 10942 (2008); doi:10.1021/jp802415t.
E. Ranucci, M.A. Suardi, R. Annunziata, P. Ferruti, F. Chiellini and C. Bartoli, Biomacromolecules, 9, 2693 (2008); doi:10.1021/bm800655s.
S. Trachtenberg and R. Gilad, Mol. Microbiol., 41, 827 (2001); doi:10.1046/j.1365-2958.2001.02527.x.
A.H. Kycia, J. Wang, A.R. Merrill and J. Lipkowski, Langmuir, 27, 10867 (2011); doi:10.1021/la2016269.