Synthesis of novel triphenylene-based discotic liquid crystals with naphthalene moiety in the side chains for photo-polymerisation

Ho Jun Song; Jang Yong Lee; Hyun Jin Lee; Doo Kyung Moon

Journal of Industrial and Engineering Chemistry, Vol.17, No.3, 445-449, May, 2011

DOI10.1016/j.jiec.2011.02.042 Export Citation

Synthesis of novel triphenylene-based discotic liquid crystals with naphthalene moiety in the side chains for photo-polymerisation

Ho Jun Song, Jang Yong Lee, Hyun Jin Lee¹, and Doo Kyung Moon^†

Department of Material Chemistry and Engineering, Konkuk University, Seoul, 143-701, Republic of Korea
¹Advanced Technology Team, Doosan Corporation Electro-Materials Research Institute, Gyeonggi-do, 449-795, Republic of Korea

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Rod-like naphthalene and the molecule 4,-(7,-(4,-(triphenylene-2,3,6,7,10,11-hexaylhexakis(oxy))hexakis(butane-4,1-diyl))hexakis(oxy)hexakis(naphthalene-7,2-diyl))hexakis(oxy)hexakis(butane-4,1-diyl) hexaacrylate, to which an acryloyl group that enabls photo-polymerisation is introduced, are synthesised nearby discotic triphenylene. Differential scanning calorimetry shows that a liquid crystalline form is observed at 69℃ . In XRD measurements, a new peak appears at 2u = 22, indicating partial nematic liquid crystalline properties. As a result of photo-polymerisation, successful polymerisation of over 70% is verified through FT-IR. UV-vis spectroscopy was used to measure the transmittance of the polymerised film, demonstrating a high transmittance level of over 94%.

Keywords:Discotic molecule;Triphenylene;Naphtalene;Photo-polymerisation

[References]

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Bushby RJ, Lozman OR, Curr. Opin. Colloid Interface Sci., 7, 343 (2002)
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Wong WWH, Singh TB, Vak D, Pisula W, Yan C, Feng XL, Williams EL, Chan KL, Mao QH, Jones DJ, Ma CQ, Mullen K, Bauerle P, Holmes AB, Adv. Funct. Mater., 20(6), 927 (2010)
Cho MY, Kim SJ, Han YD, Park DH, Kim KH, Choi DH, Joo J, Adv. Funct. Mater., 18(19), 2905 (2008)
Lee JY, Shin WS, Haw JR, Moon DK, J. Mater. Chem., 19, 4938 (2009)
Lee JY, Heo SW, Choi H, Kwon YJ, Haw JR, Moon DK, Sol. Energy Mater. Sol. Cells., 93, 1932 (2009)
Boden N, Bissell R, Clements J, Movaghar B, Liq. Cryst. Today., 6, 1 (1996)
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Moon DK, Osakada K, Maruyama T, Kubota K, Yamamoto T, Macromolecules., 26, 6992 (1993)
Lee JY, Choi MH, Moon DK, Haw JR, J. Ind. Eng. Chem., 16(3), 395 (2010)
Lee JY, Kwon YJ, Woo JW, Moon DK, J. Ind. Eng. Chem., 14(6), 810 (2008)
Kumar S, Manickam M, Mol. Cryst. Liq. Cryst., 309, 291 (1998)
Boden N, Bushby RJ, Cammidge AN, Duckworth S, Headdock G, J. Mater. Chem., 7, 601 (1997)
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[1] Chandrasekhar S, Sadashiva BK, Saresh KA, Pramana., 9, 471 (1977)

[2] Chandrasekhar S, Liq. Cryst., 14, 3 (1993)

[3] Praefcke K, Eckert A, Mol. Cryst. Liq. Cryst., 396, 265 (2003)

[4] Bushby RJ, Lozman OR, Curr. Opin. Colloid Interface Sci., 7, 343 (2002)

[5] Kumar S, Liq. Cryst., 31, 1037 (2004)

[6] Wong WWH, Singh TB, Vak D, Pisula W, Yan C, Feng XL, Williams EL, Chan KL, Mao QH, Jones DJ, Ma CQ, Mullen K, Bauerle P, Holmes AB, Adv. Funct. Mater., 20(6), 927 (2010)

[7] Cho MY, Kim SJ, Han YD, Park DH, Kim KH, Choi DH, Joo J, Adv. Funct. Mater., 18(19), 2905 (2008)

[8] Lee JY, Shin WS, Haw JR, Moon DK, J. Mater. Chem., 19, 4938 (2009)

[9] Lee JY, Heo SW, Choi H, Kwon YJ, Haw JR, Moon DK, Sol. Energy Mater. Sol. Cells., 93, 1932 (2009)

[10] Boden N, Bissell R, Clements J, Movaghar B, Liq. Cryst. Today., 6, 1 (1996)

[11] Arikainen EO, Boden N, Bushby RJ, Clements J, Movaghar B, Wood A, J. Mater.Chem., 5, 2161 (1995)

[12] Yamamoto T, Fukushima N, Nakajima H, Maruyama T, Yamaguchi I, Macromolecules, 33(16), 5988 (2000)

[13] Moon DK, Osakada K, Maruyama T, Kubota K, Yamamoto T, Macromolecules., 26, 6992 (1993)

[14] Lee JY, Choi MH, Moon DK, Haw JR, J. Ind. Eng. Chem., 16(3), 395 (2010)

[15] Lee JY, Kwon YJ, Woo JW, Moon DK, J. Ind. Eng. Chem., 14(6), 810 (2008)

[16] Kumar S, Manickam M, Mol. Cryst. Liq. Cryst., 309, 291 (1998)

[17] Boden N, Bushby RJ, Cammidge AN, Duckworth S, Headdock G, J. Mater. Chem., 7, 601 (1997)

[18] Kouwer PHJ, Mehl GH, Angew. Chem. Int. Ed., 42, 6015 (2003)

[19] Rahman ML, Tschierske V, Yusoff M, Silong S, Tetrahedron Lett., 46, 2303 (2005)

[20] Mori H, Itoh Y, Nishiura Y, Nakamura T, Shinakawa Y, Jpn. J. Appl. Phys., 36, 143 (1997)

[21] Kawata K, Chem. Rec., 2, 59 (2002)