Hostname: page-component-586b7cd67f-vdxz6 Total loading time: 0 Render date: 2024-11-23T07:35:20.908Z Has data issue: false hasContentIssue false

Thermal and photo optical properties of azoxybenzene/alkyloxy-azobenzene–cholesterol dimesogens with alkyl diacetylene linker

Published online by Cambridge University Press:  01 December 2005

Subramanian Kumaresan
Affiliation:
Molecular Smart System Group, Nanotechnology Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba 305-8565, Japan
V. Ajay Mallia
Affiliation:
Molecular Smart System Group, Nanotechnology Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba 305-8565, Japan
Yoshishige Kida
Affiliation:
Okamura Oil Mill, Ltd., Kashiwara-Shi, Osaka 582-0004, Japan
Nobuyuki Tamaoki*
Affiliation:
Molecular Smart System Group, Nanotechnology Research Institute, National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba 305-8565, Japan
*
a)Address all correspondence to this author.e-mail: [email protected]
Get access

Abstract

Thermal and photo-optical properties of azoxybenzene/alkyloxy-azobenzene containing chiral dimesogens are presented. Alkyloxyazobenzene containing dimesogenic materials exhibited two kinds of smectic A phases. Photoirradiation at temperatures exhibiting smectic phases of pure materials in azobenzene linked dimesogens resulted in formation of the isotropic phase, and this was systematically studied at different liquid crystalline temperatures. The efficacy of these compounds as a dopant in the glassy liquid crystalline material was also explored. Increasing concentration to 4 wt%/5 wt% in azobenzene/azoxy-benzene derivatives caused a dramatic red-shift in the wavelength of reflected light by the host cholesteric glassy liquid crystal. Photo-isomerization of these dopants led to a blue-shift of the reflected light, and this effect could be used to tune the light reflectivity of these mixtures over the visible region.

Type
Articles
Copyright
Copyright © Materials Research Society 2005

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

REFERENCES

1.Imrie, C.T. and Henderson, P-A.: Liquid crystal dimers and oligomers. Curr. Opin. Colloid Interface Sci. 70, 298 (2002).CrossRefGoogle Scholar
2.Imrie, C.T. and Luckhurst, G-R.: Liquid crystal dimers and oligomers, Vol. 28, edited by Demus, D., Goodby, J., Gray, G-W., Spiess, H-W., and Vill, V. (Wiley-VCH, Weinheim, Germany, 1998).Google Scholar
3.Mallia, V.A. and Tamaoki, N.: Design of chiral dimesogens containing cholesteryl groups; formation of new molecular organizations and their application to molecular photonics. Chem. Soc. Rev. 33, 76 (2004).CrossRefGoogle ScholarPubMed
4.Tamaoki, N., Parfenov, A.V., Masaki, A. and Matsuda, H.: Rewritable full-color recording on a thin solid film of a cholesteric low-molecular-weight compound. Adv. Mater. 9, 1102 (1997).CrossRefGoogle Scholar
5.Tamaoki, N., Moriyama, M. and Matsuda, H.: Cholesteric solid films formed by spin coating from solutions of dicholesteryl esters. Angew. Chem. Int. Ed. Engl. 39, 509 (2000).3.0.CO;2-W>CrossRefGoogle ScholarPubMed
6.Tamaoki, N.: Cholesteric liquid crystals for color information technology. Adv. Mater. 13, 1135 (2001).3.0.CO;2-S>CrossRefGoogle Scholar
7.Tamaoki, N., Aoki, Y., Moriyama, M. and Kidowaki, M.: Photochemical phase transition and molecular realignment of glass-forming liquid crystals containing cholesterol/azobenzene dimesogenic compounds. Chem. Mater. 15, 719 (2003).CrossRefGoogle Scholar
8.Mallia, V.A. and Tamaoki, N.: Photoresponsive vitrifiable chiral dimesogens: Photo-thermal modulation of microscopic disordering in helical superstructure and glass-forming properties. J. Mater. Chem. 13, 219 (2003).CrossRefGoogle Scholar
9.Mallia, V.A. and Tamaoki, N.: Photochemically driven smectic-cholesteric phase transition in an inherently photoactive dimesogen. Chem. Mater. 15, 3237 (2003).CrossRefGoogle Scholar
10.Mallia, V.A. and Tamaoki, N.: Photoactive dimesogen having different pathways of light driven phase transitions at different temperatures. Chem. Commun. 22, 2538 (2004).CrossRefGoogle Scholar
11.Hardouin, F., Achard, M-F., Jin, J. and Yun, Y-K.: From incommensurability to commensurability in smectic phases for a series of dimesogenic liquid-crystals. J. Phys. II France 5, 927 (1995).Google Scholar
12.Hardouin, F., Achard, M-F., Jin, J-I., Yun, Y-K. and Chung, S-J.: Competition in low ordered smectics between incommensurate phases S-ic and two-dimensional modulated ones for dimesogenic compounds. Eur. Phys. J. B 1, 47 (1998).CrossRefGoogle Scholar
13.Hardouin, F., Achard, M-F., Laguerre, M., Jin, J-I. and Ko, D-H.: Influence of the molecular length on the occurrence of incommensurate low ordered smectic phases for non-symmetric dimesogenic compounds. Liq. Cryst. 26, 589 (1999).CrossRefGoogle Scholar
14.Cha, S-W., Jin, J-I., Laguerre, M., Achard, M-F. and Hardouin, F.: Dimesogenic compounds consisting of a cholesteryl moiety and an aromatic mesogen interconnected through a central pentamethylene spacer. Liq. Cryst. 26, 1325 (1999).CrossRefGoogle Scholar
15.Lee, D.W., Jin, J-I., Laguerre, M., Achard, M.F. and Hardouin, F.: Dimesogenic compounds with an electron-attracting terminal group. Liq. Cryst. 27, 145 (2000).CrossRefGoogle Scholar
16.Lee, J-W., Park, Y., Jin, J-I., Achard, M-F. and Hardouin, F.: Comparison of the Liquid Crystalline properties of dimesogenic compounds bearing alkoxy and perfluoroalkoxy tails. J. Mater. Chem. 13, 1367 (2003).CrossRefGoogle Scholar
17.Demus, D., Goodby, J., Gray, G.W., Spiess, H-W. and Vill, V.: Handbook of Liquid Crystals (Wiley-VCH, Weinheim, Germany, 1998).Google Scholar
18.Huang, J-M., Kuo, J-F. and Chen, C-Y.: Synthesis and characterization of segmented liquid-crystal poly(azoxy polyester-co-polyoxypropylene). J. Polym. Sci., Part A: Polym. Chem. 33, 165 (1995).CrossRefGoogle Scholar
19.Wilbert, G. and Zentel, R.: Liquid crystalline main-chain polymers containing the ferrocene unit as a side group. Macromol. Chem. Phys. 197, 3259 (1996).CrossRefGoogle Scholar
20.Wilbert, G., Traud, S. and Zentel, R.: Liquid crystalline main chain polymers containing the ferrocene unit as a side group, 2. Variation of the spacer length. Macromol. Chem. Phys. 198, 3769 (1997).CrossRefGoogle Scholar
21.Serrano, J.L.: Metallomesogens (VCH, Weinheim, Germany, 1996).Google Scholar
22.Tamaoki, N., Song, S., Moriyama, M. and Matsuda, H.: Rewritable full-colour recording in a photon mode. Adv. Mater. 12, 94 (2000).3.0.CO;2-T>CrossRefGoogle Scholar
23.Moriyama, M., Tamaoki, N., Song, S. and Matsuda, H.: Effects of doped 4,4′-dialkylazobenzenes on helical pitch of cholesteric liquid crystal with medium molecular weight: Utilization of cholesteric reflected color for photo-rewritable color imaging. J. Mater. Chem. 11, 1003 (2001).CrossRefGoogle Scholar
24.Moriyama, M. and Tamaoki, N.: Photo-controllable and fixable optical properties of non-polymeric liquid crystals with azobenzene chromophore, Chem. Lett. 30(11), 1142 (2001).CrossRefGoogle Scholar
25.Kidowaki, M., Moriyama, M., Wada, M. and Tamaoki, N.: Molecular mechanisum of anomalous increase in the helical pitch of cholesteric liquid crystals induced by achiral dopants. J. Phys. Chem. B 107, 12054 (2003).CrossRefGoogle Scholar
26.Furniss, B.S., Hannaford, A.J., Smith, P.W.G. and Tatchell, A.R.: Vogel’s Textbook of Practical Organic Chemistry (Pearson Education Limited, London, U.K., 1989).Google Scholar
27.Blatch, A.E., Fletcher, I.D. and Luckhurst, G.R.: The intercalated smectic A phase—the liquid crystal properties of the alpha(4-cyanobiphenyl-4′-yloxy)-omega-(4-alkyloxycinnamoate) alkanes. Liq. Cryst. 18, 801 (1995).CrossRefGoogle Scholar
28.Marcelis, A.T.M., Koudijs, A., Klop, E.A. and Sudholter, E.J.R.: Influence of spacer and terminal group lengths on the smectic ordering of cholesterol-containing dimer liquid crystals. Liq. Cryst. 28, 881 (2001).CrossRefGoogle Scholar
29.Ichimura, K.: Photoalignment of liquid-crystal systems. Chem. Rev. 100, 1847 (2000).CrossRefGoogle ScholarPubMed
30.Ikeda, T.: Photomodulation of liquid crystal orientations for photonic applications. J. Mater. Chem. 13, 2037 (2003).CrossRefGoogle Scholar
31.Ikeda, T., Sasaki, T. and Ichimura, K.: Photochemical switching of polarization in ferroelectric liquid-crystal films. Nature 361, 428 (1993).CrossRefGoogle Scholar
32.Ikeda, T. and Tsutsumi, O.: Optical switching and image storage by means of azobenzene liquid-crystal films. Science 268, 1873 (1995).CrossRefGoogle ScholarPubMed
33.Sackmann, E.: Photochemically induced reversible color changes in cholesteric liquid crystals. J. Am. Chem. Soc. 93, 7088 (1971).CrossRefGoogle Scholar
34.Ruslim, C. and Ichimura, K.: Conformational effect on macroscopic chirality modification of cholesteric mesophases by photochromic azobenzene dopants. J. Phys. Chem. B 104, 6529 (2000).CrossRefGoogle Scholar
35.George, M., Mallia, V.A., Antharjanam, P.K.S., Saminathan, M. and Das, S.: Synthesis and studies of some cholesterol containing liquid crystals. Mol. Cryst. Liq. Cryst. 350, 125 (2000).CrossRefGoogle Scholar
36.Lee, H-K., Doi, K., Hirada, H., Tsutsumi, O., Kanazawa, A., Shiono, T. and Ikeda, T.: Photochemical modulation of color and transmittance in chiral nematic liquid crystal containing an azobenzene as a photosensitive chromophore. J. Phys. Chem. B 104, 7023 (2000).CrossRefGoogle Scholar
37.Kurihara, S., Nomiyama, S. and Nonaka, T.: Photochemical switching between a compensated nematic phase and a twisted nematic phase by photoisomerization of chiral azobenzene molecules. Chem. Mater. 12, 9 (2000).CrossRefGoogle Scholar
38.Burnham, K.S. and Schuster, G.B.: Transfer of chirality from circularly polarized light to a bulk material property: Propagation of photoresolution by a liquid crystal transition. J. Am. Chem. Soc. 121, 10245 (1999).CrossRefGoogle Scholar
39.van Delden, R.A., van Gelder, M.B., Huck, N.P.M. and Feringa, B.L.: Controlling the color of cholesteric liquid-crystalline films by photoirradiation of a chiroptical molecular switch used as dopant. Adv. Funct. Mater. 13, 319 (2003).CrossRefGoogle Scholar
40.Davis, R., Mallia, V.A., Das, S. and Tamaoki, N.: Butadienes as novel photochromophores for color tuning of cholesteric glasses: Influence of microscopic molecular reorganization within the helical superstructure. Adv. Funct. Mater. 14(8) 743 (2004).CrossRefGoogle Scholar
41.Bobrovsky, A.Y. and Shibaev, V.P.: Chiral nematic polymer mixture containing crosslinker and photosensitive chiral dopant: New type of materials with tunable photo-optical properties. Adv. Funct. Mater. 12, 367 (2002).3.0.CO;2-L>CrossRefGoogle Scholar