Abstract

A series of ortho fluoro-tolane liquid crystals was prepared via multi-step reactions based on 4-alkylcyclohexanecarboxylic acids. Their synthetic routes, thermotropic mesophases and UV stability properties are discussed by comparision with the non-fluorinated analogs. All of the measurements from DSC, UV-vis absorption and fluorescence emission spectra demonstrate that the presence of ortho fluorine can significantly improve the UV stability of tolane-liquid crystals. Meanwhile, the ultimate failure mechanism of tolane-LCs during UV exposure is deduced by a photochemical reaction. DFT calculations of molecular polarizabilities, triple bond lengths, electrostatic potential maps and molecular orbitals are used to correlate the experimental findings. The interaction mechanism for stabilization of the tolane structures by the ortho fluoro substitution is also explained. This work may provide an effective solution for the obstacle existed in tolane-liquid crystals and pave a way for their applications in liquid crystal photonics.

© 2015 Optical Society of America

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    [Crossref]
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2015 (2)

R. Chen, Y. Jiang, J. Li, Z. An, X. Chen, and P. Chen, “Dielectric and optical anisotropy enhanced by 1,3-dioxolane terminal substitution on tolane-liquid crystals,” J. Mater. Chem. C Mater. Opt. Electron. Devices 3(33), 8706–8711 (2015).
[Crossref]

Z. Luo, F. Peng, H. Chen, M. Hu, J. Li, Z. An, and S.-T. Wu, “Fast-response liquid crystals for high image quality wearable displays,” Opt. Mater. Express 5(3), 603–610 (2015).
[Crossref]

2014 (5)

R. Chen, Z. W. An, X. B. Chen, and P. Chen, “Syntheses and properties of four-ring liquid crystals with ethylene and internal alkyne bridge,” Chem. J. Chinese Universities 35(7), 1433–1438 (2014).

A. Yuki, K. Sungmin, N. Shunpei, S. Koichi, K. Susumu, W. Junji, and K. Genichi, “Synthesis of new wide nematic diaryl-diacetylenes containing thiophene-based heteromonocyclic and heterobicyclic structures, and their birefringence properties,” Liq. Cryst. 41(5), 642–651 (2014).
[Crossref]

P. L. Praveen and P. O. Durga, “Effect of substituent on UV-visible absorption and photostability of liquid crystals: DFT study,” Phase Transit. 87(5), 515–525 (2014).
[Crossref]

M. Zhang, X. Guo, S. Zhang, and J. Hou, “Synergistic effect of fluorination on molecular energy level modulation in highly efficient photovoltaic polymers,” Adv. Mater. 26(7), 1118–1123 (2014).
[Crossref] [PubMed]

G. Y. Si, Y. H. Zhao, E. S. P. Leong, and Y. J. Liu, “Liquid-crystal-enabled active plasmonics: a review,” Materials (Basel) 7(2), 1296–1317 (2014).
[Crossref]

2013 (3)

R. Dąbrowski, P. Kula, and J. Herman, “High birefringence liquid crystals,” Crystals 3(3), 443–482 (2013).
[Crossref]

T. Geelhaar, K. Griesar, and B. Reckmann, “125 years of liquid crystals--a scientific revolution in the home,” Angew. Chem. Int. Ed. Engl. 52(34), 8798–8809 (2013).
[Crossref] [PubMed]

B. Li, W. He, L. Wang, X. Xiao, and H. Yang, “Effect of lateral fluoro substituents of rodlike tolane cyano mesogens on blue phase temperature ranges,” Soft Matter 9(4), 1172–1177 (2013).
[Crossref]

2012 (2)

2011 (1)

2009 (1)

I. C. Khoo, S. Webster, S. Kubo, W. J. Youngblood, J. D. Liou, T. E. Mallouk, P. Lin, D. J. Hagan, and S. E. W. Van, “Synthesis and characterization of the multi-photon absorption and excited-state properties of a neat liquid 4-propyl 4′-butyl diphenyl acetylene,” J. Mater. Chem. 19(40), 7525–7531 (2009).
[Crossref]

2007 (4)

L. Hunter, A. M. Z. Slawin, P. Kirsch, and D. O’Hagan, “Synthesis and conformation of multi-vicinal fluoroalkane diastereoisomers,” Angew. Chem. Int. Ed. Engl. 46(41), 7887–7890 (2007).
[Crossref] [PubMed]

S. Gauza, X. Zhu, K. Piecek, R. Dąbrowski, and S. T. Wu, “Fast switching liquid crystals for color-sequential LCDs,” J. Disp. Technol. 3(3), 250–252 (2007).
[Crossref]

M. Hird, “Fluorinated liquid crystals--properties and applications,” Chem. Soc. Rev. 36(12), 2070–2095 (2007).
[Crossref] [PubMed]

Y. M. Liao, H. L. Chen, C. S. Hsu, S. Gauza, and S. T. Wu, “Synthesis and mesomorphic properties of super high birefringence isothiocyanato bistolane liquid crystals,” Liq. Cryst. 34(4), 507–517 (2007).
[Crossref]

2006 (1)

S. Gauza, C. H. Wen, B. Wu, S. T. Wu, A. Spadlo, and R. Dąbrowski, “Fast-response nematic liquid-crystal mixtures,” Journal of the SID 14(3), 241–246 (2006).

2005 (1)

S. Gauza, C. H. Wen, S. T. Wu, R. Dąbrowski, C. S. Hsu, C. O. Catanescu, and L. C. Chien, “High birefringence liquid crystals for photonic applications,” Proc. SPIE 5947, 594706 (2005).
[Crossref]

2004 (3)

P. T. Lin, S. T. Wu, C. Y. Chang, and C. S. Hsu, “UV stability of high birefringence liquid crystals,” Mol. Cryst. Liq. Cryst. (Phila. Pa.) 411(1), 1285–1295 (2004).
[Crossref]

S. Gauza, C. H. Wen, B. J. Tan, and S. T. Wu, “UV stable high birefringence liquid crystals,” Jpn. J. Appl. Phys. 43(10), 7176–7180 (2004).
[Crossref]

C. H. Wen, S. Gauza, and S. T. Wu, “Ultraviolet stability of liquid crystals containing cyano and isothiocyanato terminal groups,” Liq. Cryst. 31(11), 1479–1485 (2004).
[Crossref]

2001 (1)

H. F. Chow, C. W. Wan, K. H. Low, and Y. Y. Yeung, “A highly selective synthesis of diarylethynes and their oligomers by a palladium-catalyzed Sonogashira coupling reaction under phase transfer conditions,” J. Org. Chem. 66(5), 1910–1913 (2001).
[Crossref] [PubMed]

1990 (1)

S. T. Wu, E. Ramos, and U. Finkenzeller, “Polarized UV spectroscopy of conjugated liquid crystals,” J. Appl. Phys. 68(1), 78–85 (1990).
[Crossref]

An, Z.

R. Chen, Y. Jiang, J. Li, Z. An, X. Chen, and P. Chen, “Dielectric and optical anisotropy enhanced by 1,3-dioxolane terminal substitution on tolane-liquid crystals,” J. Mater. Chem. C Mater. Opt. Electron. Devices 3(33), 8706–8711 (2015).
[Crossref]

Z. Luo, F. Peng, H. Chen, M. Hu, J. Li, Z. An, and S.-T. Wu, “Fast-response liquid crystals for high image quality wearable displays,” Opt. Mater. Express 5(3), 603–610 (2015).
[Crossref]

An, Z. W.

R. Chen, Z. W. An, X. B. Chen, and P. Chen, “Syntheses and properties of four-ring liquid crystals with ethylene and internal alkyne bridge,” Chem. J. Chinese Universities 35(7), 1433–1438 (2014).

Bae, W. K.

Catanescu, C. O.

S. Gauza, C. H. Wen, S. T. Wu, R. Dąbrowski, C. S. Hsu, C. O. Catanescu, and L. C. Chien, “High birefringence liquid crystals for photonic applications,” Proc. SPIE 5947, 594706 (2005).
[Crossref]

Chang, C. Y.

P. T. Lin, S. T. Wu, C. Y. Chang, and C. S. Hsu, “UV stability of high birefringence liquid crystals,” Mol. Cryst. Liq. Cryst. (Phila. Pa.) 411(1), 1285–1295 (2004).
[Crossref]

Char, K.

Chen, H.

Chen, H. L.

Y. M. Liao, H. L. Chen, C. S. Hsu, S. Gauza, and S. T. Wu, “Synthesis and mesomorphic properties of super high birefringence isothiocyanato bistolane liquid crystals,” Liq. Cryst. 34(4), 507–517 (2007).
[Crossref]

Chen, P.

R. Chen, Y. Jiang, J. Li, Z. An, X. Chen, and P. Chen, “Dielectric and optical anisotropy enhanced by 1,3-dioxolane terminal substitution on tolane-liquid crystals,” J. Mater. Chem. C Mater. Opt. Electron. Devices 3(33), 8706–8711 (2015).
[Crossref]

R. Chen, Z. W. An, X. B. Chen, and P. Chen, “Syntheses and properties of four-ring liquid crystals with ethylene and internal alkyne bridge,” Chem. J. Chinese Universities 35(7), 1433–1438 (2014).

Chen, R.

R. Chen, Y. Jiang, J. Li, Z. An, X. Chen, and P. Chen, “Dielectric and optical anisotropy enhanced by 1,3-dioxolane terminal substitution on tolane-liquid crystals,” J. Mater. Chem. C Mater. Opt. Electron. Devices 3(33), 8706–8711 (2015).
[Crossref]

R. Chen, Z. W. An, X. B. Chen, and P. Chen, “Syntheses and properties of four-ring liquid crystals with ethylene and internal alkyne bridge,” Chem. J. Chinese Universities 35(7), 1433–1438 (2014).

Chen, X.

R. Chen, Y. Jiang, J. Li, Z. An, X. Chen, and P. Chen, “Dielectric and optical anisotropy enhanced by 1,3-dioxolane terminal substitution on tolane-liquid crystals,” J. Mater. Chem. C Mater. Opt. Electron. Devices 3(33), 8706–8711 (2015).
[Crossref]

Chen, X. B.

R. Chen, Z. W. An, X. B. Chen, and P. Chen, “Syntheses and properties of four-ring liquid crystals with ethylene and internal alkyne bridge,” Chem. J. Chinese Universities 35(7), 1433–1438 (2014).

Chien, L. C.

S. Gauza, C. H. Wen, S. T. Wu, R. Dąbrowski, C. S. Hsu, C. O. Catanescu, and L. C. Chien, “High birefringence liquid crystals for photonic applications,” Proc. SPIE 5947, 594706 (2005).
[Crossref]

Chow, H. F.

H. F. Chow, C. W. Wan, K. H. Low, and Y. Y. Yeung, “A highly selective synthesis of diarylethynes and their oligomers by a palladium-catalyzed Sonogashira coupling reaction under phase transfer conditions,” J. Org. Chem. 66(5), 1910–1913 (2001).
[Crossref] [PubMed]

Dabrowski, R.

R. Dąbrowski, P. Kula, and J. Herman, “High birefringence liquid crystals,” Crystals 3(3), 443–482 (2013).
[Crossref]

S. Gauza, X. Zhu, K. Piecek, R. Dąbrowski, and S. T. Wu, “Fast switching liquid crystals for color-sequential LCDs,” J. Disp. Technol. 3(3), 250–252 (2007).
[Crossref]

S. Gauza, C. H. Wen, B. Wu, S. T. Wu, A. Spadlo, and R. Dąbrowski, “Fast-response nematic liquid-crystal mixtures,” Journal of the SID 14(3), 241–246 (2006).

S. Gauza, C. H. Wen, S. T. Wu, R. Dąbrowski, C. S. Hsu, C. O. Catanescu, and L. C. Chien, “High birefringence liquid crystals for photonic applications,” Proc. SPIE 5947, 594706 (2005).
[Crossref]

Durga, P. O.

P. L. Praveen and P. O. Durga, “Effect of substituent on UV-visible absorption and photostability of liquid crystals: DFT study,” Phase Transit. 87(5), 515–525 (2014).
[Crossref]

Finkenzeller, U.

S. T. Wu, E. Ramos, and U. Finkenzeller, “Polarized UV spectroscopy of conjugated liquid crystals,” J. Appl. Phys. 68(1), 78–85 (1990).
[Crossref]

Gauza, S.

S. Gauza, X. Zhu, K. Piecek, R. Dąbrowski, and S. T. Wu, “Fast switching liquid crystals for color-sequential LCDs,” J. Disp. Technol. 3(3), 250–252 (2007).
[Crossref]

Y. M. Liao, H. L. Chen, C. S. Hsu, S. Gauza, and S. T. Wu, “Synthesis and mesomorphic properties of super high birefringence isothiocyanato bistolane liquid crystals,” Liq. Cryst. 34(4), 507–517 (2007).
[Crossref]

S. Gauza, C. H. Wen, B. Wu, S. T. Wu, A. Spadlo, and R. Dąbrowski, “Fast-response nematic liquid-crystal mixtures,” Journal of the SID 14(3), 241–246 (2006).

S. Gauza, C. H. Wen, S. T. Wu, R. Dąbrowski, C. S. Hsu, C. O. Catanescu, and L. C. Chien, “High birefringence liquid crystals for photonic applications,” Proc. SPIE 5947, 594706 (2005).
[Crossref]

C. H. Wen, S. Gauza, and S. T. Wu, “Ultraviolet stability of liquid crystals containing cyano and isothiocyanato terminal groups,” Liq. Cryst. 31(11), 1479–1485 (2004).
[Crossref]

S. Gauza, C. H. Wen, B. J. Tan, and S. T. Wu, “UV stable high birefringence liquid crystals,” Jpn. J. Appl. Phys. 43(10), 7176–7180 (2004).
[Crossref]

Geelhaar, T.

T. Geelhaar, K. Griesar, and B. Reckmann, “125 years of liquid crystals--a scientific revolution in the home,” Angew. Chem. Int. Ed. Engl. 52(34), 8798–8809 (2013).
[Crossref] [PubMed]

Genichi, K.

A. Yuki, K. Sungmin, N. Shunpei, S. Koichi, K. Susumu, W. Junji, and K. Genichi, “Synthesis of new wide nematic diaryl-diacetylenes containing thiophene-based heteromonocyclic and heterobicyclic structures, and their birefringence properties,” Liq. Cryst. 41(5), 642–651 (2014).
[Crossref]

Griesar, K.

T. Geelhaar, K. Griesar, and B. Reckmann, “125 years of liquid crystals--a scientific revolution in the home,” Angew. Chem. Int. Ed. Engl. 52(34), 8798–8809 (2013).
[Crossref] [PubMed]

Guo, X.

M. Zhang, X. Guo, S. Zhang, and J. Hou, “Synergistic effect of fluorination on molecular energy level modulation in highly efficient photovoltaic polymers,” Adv. Mater. 26(7), 1118–1123 (2014).
[Crossref] [PubMed]

Hagan, D. J.

I. C. Khoo, S. Webster, S. Kubo, W. J. Youngblood, J. D. Liou, T. E. Mallouk, P. Lin, D. J. Hagan, and S. E. W. Van, “Synthesis and characterization of the multi-photon absorption and excited-state properties of a neat liquid 4-propyl 4′-butyl diphenyl acetylene,” J. Mater. Chem. 19(40), 7525–7531 (2009).
[Crossref]

He, W.

B. Li, W. He, L. Wang, X. Xiao, and H. Yang, “Effect of lateral fluoro substituents of rodlike tolane cyano mesogens on blue phase temperature ranges,” Soft Matter 9(4), 1172–1177 (2013).
[Crossref]

Herman, J.

R. Dąbrowski, P. Kula, and J. Herman, “High birefringence liquid crystals,” Crystals 3(3), 443–482 (2013).
[Crossref]

Hird, M.

M. Hird, “Fluorinated liquid crystals--properties and applications,” Chem. Soc. Rev. 36(12), 2070–2095 (2007).
[Crossref] [PubMed]

Hou, J.

M. Zhang, X. Guo, S. Zhang, and J. Hou, “Synergistic effect of fluorination on molecular energy level modulation in highly efficient photovoltaic polymers,” Adv. Mater. 26(7), 1118–1123 (2014).
[Crossref] [PubMed]

Hsu, C. S.

Y. M. Liao, H. L. Chen, C. S. Hsu, S. Gauza, and S. T. Wu, “Synthesis and mesomorphic properties of super high birefringence isothiocyanato bistolane liquid crystals,” Liq. Cryst. 34(4), 507–517 (2007).
[Crossref]

S. Gauza, C. H. Wen, S. T. Wu, R. Dąbrowski, C. S. Hsu, C. O. Catanescu, and L. C. Chien, “High birefringence liquid crystals for photonic applications,” Proc. SPIE 5947, 594706 (2005).
[Crossref]

P. T. Lin, S. T. Wu, C. Y. Chang, and C. S. Hsu, “UV stability of high birefringence liquid crystals,” Mol. Cryst. Liq. Cryst. (Phila. Pa.) 411(1), 1285–1295 (2004).
[Crossref]

Hu, M.

Hu, W.

Hunter, L.

L. Hunter, A. M. Z. Slawin, P. Kirsch, and D. O’Hagan, “Synthesis and conformation of multi-vicinal fluoroalkane diastereoisomers,” Angew. Chem. Int. Ed. Engl. 46(41), 7887–7890 (2007).
[Crossref] [PubMed]

Jiang, Y.

R. Chen, Y. Jiang, J. Li, Z. An, X. Chen, and P. Chen, “Dielectric and optical anisotropy enhanced by 1,3-dioxolane terminal substitution on tolane-liquid crystals,” J. Mater. Chem. C Mater. Opt. Electron. Devices 3(33), 8706–8711 (2015).
[Crossref]

Jin, B.

Junji, W.

A. Yuki, K. Sungmin, N. Shunpei, S. Koichi, K. Susumu, W. Junji, and K. Genichi, “Synthesis of new wide nematic diaryl-diacetylenes containing thiophene-based heteromonocyclic and heterobicyclic structures, and their birefringence properties,” Liq. Cryst. 41(5), 642–651 (2014).
[Crossref]

Khoo, I. C.

I. C. Khoo, S. Webster, S. Kubo, W. J. Youngblood, J. D. Liou, T. E. Mallouk, P. Lin, D. J. Hagan, and S. E. W. Van, “Synthesis and characterization of the multi-photon absorption and excited-state properties of a neat liquid 4-propyl 4′-butyl diphenyl acetylene,” J. Mater. Chem. 19(40), 7525–7531 (2009).
[Crossref]

Kirsch, P.

L. Hunter, A. M. Z. Slawin, P. Kirsch, and D. O’Hagan, “Synthesis and conformation of multi-vicinal fluoroalkane diastereoisomers,” Angew. Chem. Int. Ed. Engl. 46(41), 7887–7890 (2007).
[Crossref] [PubMed]

Koichi, S.

A. Yuki, K. Sungmin, N. Shunpei, S. Koichi, K. Susumu, W. Junji, and K. Genichi, “Synthesis of new wide nematic diaryl-diacetylenes containing thiophene-based heteromonocyclic and heterobicyclic structures, and their birefringence properties,” Liq. Cryst. 41(5), 642–651 (2014).
[Crossref]

Kubo, S.

I. C. Khoo, S. Webster, S. Kubo, W. J. Youngblood, J. D. Liou, T. E. Mallouk, P. Lin, D. J. Hagan, and S. E. W. Van, “Synthesis and characterization of the multi-photon absorption and excited-state properties of a neat liquid 4-propyl 4′-butyl diphenyl acetylene,” J. Mater. Chem. 19(40), 7525–7531 (2009).
[Crossref]

Kula, P.

R. Dąbrowski, P. Kula, and J. Herman, “High birefringence liquid crystals,” Crystals 3(3), 443–482 (2013).
[Crossref]

Kwak, J.

Lee, C.

Lee, S.

Lee, W.

Leong, E. S. P.

G. Y. Si, Y. H. Zhao, E. S. P. Leong, and Y. J. Liu, “Liquid-crystal-enabled active plasmonics: a review,” Materials (Basel) 7(2), 1296–1317 (2014).
[Crossref]

Li, B.

B. Li, W. He, L. Wang, X. Xiao, and H. Yang, “Effect of lateral fluoro substituents of rodlike tolane cyano mesogens on blue phase temperature ranges,” Soft Matter 9(4), 1172–1177 (2013).
[Crossref]

Li, J.

R. Chen, Y. Jiang, J. Li, Z. An, X. Chen, and P. Chen, “Dielectric and optical anisotropy enhanced by 1,3-dioxolane terminal substitution on tolane-liquid crystals,” J. Mater. Chem. C Mater. Opt. Electron. Devices 3(33), 8706–8711 (2015).
[Crossref]

Z. Luo, F. Peng, H. Chen, M. Hu, J. Li, Z. An, and S.-T. Wu, “Fast-response liquid crystals for high image quality wearable displays,” Opt. Mater. Express 5(3), 603–610 (2015).
[Crossref]

Liang, X.

Liao, Y. M.

Y. M. Liao, H. L. Chen, C. S. Hsu, S. Gauza, and S. T. Wu, “Synthesis and mesomorphic properties of super high birefringence isothiocyanato bistolane liquid crystals,” Liq. Cryst. 34(4), 507–517 (2007).
[Crossref]

Lim, J.

Lin, P.

I. C. Khoo, S. Webster, S. Kubo, W. J. Youngblood, J. D. Liou, T. E. Mallouk, P. Lin, D. J. Hagan, and S. E. W. Van, “Synthesis and characterization of the multi-photon absorption and excited-state properties of a neat liquid 4-propyl 4′-butyl diphenyl acetylene,” J. Mater. Chem. 19(40), 7525–7531 (2009).
[Crossref]

Lin, P. T.

P. T. Lin, S. T. Wu, C. Y. Chang, and C. S. Hsu, “UV stability of high birefringence liquid crystals,” Mol. Cryst. Liq. Cryst. (Phila. Pa.) 411(1), 1285–1295 (2004).
[Crossref]

Lin, X.

Liou, J. D.

I. C. Khoo, S. Webster, S. Kubo, W. J. Youngblood, J. D. Liou, T. E. Mallouk, P. Lin, D. J. Hagan, and S. E. W. Van, “Synthesis and characterization of the multi-photon absorption and excited-state properties of a neat liquid 4-propyl 4′-butyl diphenyl acetylene,” J. Mater. Chem. 19(40), 7525–7531 (2009).
[Crossref]

Liu, Y. J.

G. Y. Si, Y. H. Zhao, E. S. P. Leong, and Y. J. Liu, “Liquid-crystal-enabled active plasmonics: a review,” Materials (Basel) 7(2), 1296–1317 (2014).
[Crossref]

Low, K. H.

H. F. Chow, C. W. Wan, K. H. Low, and Y. Y. Yeung, “A highly selective synthesis of diarylethynes and their oligomers by a palladium-catalyzed Sonogashira coupling reaction under phase transfer conditions,” J. Org. Chem. 66(5), 1910–1913 (2001).
[Crossref] [PubMed]

Lu, Y.

Luo, Z.

Mallouk, T. E.

I. C. Khoo, S. Webster, S. Kubo, W. J. Youngblood, J. D. Liou, T. E. Mallouk, P. Lin, D. J. Hagan, and S. E. W. Van, “Synthesis and characterization of the multi-photon absorption and excited-state properties of a neat liquid 4-propyl 4′-butyl diphenyl acetylene,” J. Mater. Chem. 19(40), 7525–7531 (2009).
[Crossref]

O’Hagan, D.

L. Hunter, A. M. Z. Slawin, P. Kirsch, and D. O’Hagan, “Synthesis and conformation of multi-vicinal fluoroalkane diastereoisomers,” Angew. Chem. Int. Ed. Engl. 46(41), 7887–7890 (2007).
[Crossref] [PubMed]

Peng, F.

Piecek, K.

S. Gauza, X. Zhu, K. Piecek, R. Dąbrowski, and S. T. Wu, “Fast switching liquid crystals for color-sequential LCDs,” J. Disp. Technol. 3(3), 250–252 (2007).
[Crossref]

Praveen, P. L.

P. L. Praveen and P. O. Durga, “Effect of substituent on UV-visible absorption and photostability of liquid crystals: DFT study,” Phase Transit. 87(5), 515–525 (2014).
[Crossref]

Qin, Y.

Ramos, E.

S. T. Wu, E. Ramos, and U. Finkenzeller, “Polarized UV spectroscopy of conjugated liquid crystals,” J. Appl. Phys. 68(1), 78–85 (1990).
[Crossref]

Reckmann, B.

T. Geelhaar, K. Griesar, and B. Reckmann, “125 years of liquid crystals--a scientific revolution in the home,” Angew. Chem. Int. Ed. Engl. 52(34), 8798–8809 (2013).
[Crossref] [PubMed]

Shunpei, N.

A. Yuki, K. Sungmin, N. Shunpei, S. Koichi, K. Susumu, W. Junji, and K. Genichi, “Synthesis of new wide nematic diaryl-diacetylenes containing thiophene-based heteromonocyclic and heterobicyclic structures, and their birefringence properties,” Liq. Cryst. 41(5), 642–651 (2014).
[Crossref]

Si, G. Y.

G. Y. Si, Y. H. Zhao, E. S. P. Leong, and Y. J. Liu, “Liquid-crystal-enabled active plasmonics: a review,” Materials (Basel) 7(2), 1296–1317 (2014).
[Crossref]

Slawin, A. M. Z.

L. Hunter, A. M. Z. Slawin, P. Kirsch, and D. O’Hagan, “Synthesis and conformation of multi-vicinal fluoroalkane diastereoisomers,” Angew. Chem. Int. Ed. Engl. 46(41), 7887–7890 (2007).
[Crossref] [PubMed]

Spadlo, A.

S. Gauza, C. H. Wen, B. Wu, S. T. Wu, A. Spadlo, and R. Dąbrowski, “Fast-response nematic liquid-crystal mixtures,” Journal of the SID 14(3), 241–246 (2006).

Sungmin, K.

A. Yuki, K. Sungmin, N. Shunpei, S. Koichi, K. Susumu, W. Junji, and K. Genichi, “Synthesis of new wide nematic diaryl-diacetylenes containing thiophene-based heteromonocyclic and heterobicyclic structures, and their birefringence properties,” Liq. Cryst. 41(5), 642–651 (2014).
[Crossref]

Susumu, K.

A. Yuki, K. Sungmin, N. Shunpei, S. Koichi, K. Susumu, W. Junji, and K. Genichi, “Synthesis of new wide nematic diaryl-diacetylenes containing thiophene-based heteromonocyclic and heterobicyclic structures, and their birefringence properties,” Liq. Cryst. 41(5), 642–651 (2014).
[Crossref]

Tan, B. J.

S. Gauza, C. H. Wen, B. J. Tan, and S. T. Wu, “UV stable high birefringence liquid crystals,” Jpn. J. Appl. Phys. 43(10), 7176–7180 (2004).
[Crossref]

Van, S. E. W.

I. C. Khoo, S. Webster, S. Kubo, W. J. Youngblood, J. D. Liou, T. E. Mallouk, P. Lin, D. J. Hagan, and S. E. W. Van, “Synthesis and characterization of the multi-photon absorption and excited-state properties of a neat liquid 4-propyl 4′-butyl diphenyl acetylene,” J. Mater. Chem. 19(40), 7525–7531 (2009).
[Crossref]

Wan, C. W.

H. F. Chow, C. W. Wan, K. H. Low, and Y. Y. Yeung, “A highly selective synthesis of diarylethynes and their oligomers by a palladium-catalyzed Sonogashira coupling reaction under phase transfer conditions,” J. Org. Chem. 66(5), 1910–1913 (2001).
[Crossref] [PubMed]

Wang, L.

B. Li, W. He, L. Wang, X. Xiao, and H. Yang, “Effect of lateral fluoro substituents of rodlike tolane cyano mesogens on blue phase temperature ranges,” Soft Matter 9(4), 1172–1177 (2013).
[Crossref]

L. Wang, X. Lin, X. Liang, J. Wu, W. Hu, Z. Zheng, B. Jin, Y. Qin, and Y. Lu, “Large birefringence liquid crystal material in terahertz range,” Opt. Mater. Express 2(10), 1314–1319 (2012).
[Crossref]

Webster, S.

I. C. Khoo, S. Webster, S. Kubo, W. J. Youngblood, J. D. Liou, T. E. Mallouk, P. Lin, D. J. Hagan, and S. E. W. Van, “Synthesis and characterization of the multi-photon absorption and excited-state properties of a neat liquid 4-propyl 4′-butyl diphenyl acetylene,” J. Mater. Chem. 19(40), 7525–7531 (2009).
[Crossref]

Wen, C. H.

S. Gauza, C. H. Wen, B. Wu, S. T. Wu, A. Spadlo, and R. Dąbrowski, “Fast-response nematic liquid-crystal mixtures,” Journal of the SID 14(3), 241–246 (2006).

S. Gauza, C. H. Wen, S. T. Wu, R. Dąbrowski, C. S. Hsu, C. O. Catanescu, and L. C. Chien, “High birefringence liquid crystals for photonic applications,” Proc. SPIE 5947, 594706 (2005).
[Crossref]

C. H. Wen, S. Gauza, and S. T. Wu, “Ultraviolet stability of liquid crystals containing cyano and isothiocyanato terminal groups,” Liq. Cryst. 31(11), 1479–1485 (2004).
[Crossref]

S. Gauza, C. H. Wen, B. J. Tan, and S. T. Wu, “UV stable high birefringence liquid crystals,” Jpn. J. Appl. Phys. 43(10), 7176–7180 (2004).
[Crossref]

Wu, B.

S. Gauza, C. H. Wen, B. Wu, S. T. Wu, A. Spadlo, and R. Dąbrowski, “Fast-response nematic liquid-crystal mixtures,” Journal of the SID 14(3), 241–246 (2006).

Wu, J.

Wu, S. T.

S. Gauza, X. Zhu, K. Piecek, R. Dąbrowski, and S. T. Wu, “Fast switching liquid crystals for color-sequential LCDs,” J. Disp. Technol. 3(3), 250–252 (2007).
[Crossref]

Y. M. Liao, H. L. Chen, C. S. Hsu, S. Gauza, and S. T. Wu, “Synthesis and mesomorphic properties of super high birefringence isothiocyanato bistolane liquid crystals,” Liq. Cryst. 34(4), 507–517 (2007).
[Crossref]

S. Gauza, C. H. Wen, B. Wu, S. T. Wu, A. Spadlo, and R. Dąbrowski, “Fast-response nematic liquid-crystal mixtures,” Journal of the SID 14(3), 241–246 (2006).

S. Gauza, C. H. Wen, S. T. Wu, R. Dąbrowski, C. S. Hsu, C. O. Catanescu, and L. C. Chien, “High birefringence liquid crystals for photonic applications,” Proc. SPIE 5947, 594706 (2005).
[Crossref]

C. H. Wen, S. Gauza, and S. T. Wu, “Ultraviolet stability of liquid crystals containing cyano and isothiocyanato terminal groups,” Liq. Cryst. 31(11), 1479–1485 (2004).
[Crossref]

S. Gauza, C. H. Wen, B. J. Tan, and S. T. Wu, “UV stable high birefringence liquid crystals,” Jpn. J. Appl. Phys. 43(10), 7176–7180 (2004).
[Crossref]

P. T. Lin, S. T. Wu, C. Y. Chang, and C. S. Hsu, “UV stability of high birefringence liquid crystals,” Mol. Cryst. Liq. Cryst. (Phila. Pa.) 411(1), 1285–1295 (2004).
[Crossref]

S. T. Wu, E. Ramos, and U. Finkenzeller, “Polarized UV spectroscopy of conjugated liquid crystals,” J. Appl. Phys. 68(1), 78–85 (1990).
[Crossref]

Wu, S.-T.

Xiao, X.

B. Li, W. He, L. Wang, X. Xiao, and H. Yang, “Effect of lateral fluoro substituents of rodlike tolane cyano mesogens on blue phase temperature ranges,” Soft Matter 9(4), 1172–1177 (2013).
[Crossref]

Yang, H.

B. Li, W. He, L. Wang, X. Xiao, and H. Yang, “Effect of lateral fluoro substituents of rodlike tolane cyano mesogens on blue phase temperature ranges,” Soft Matter 9(4), 1172–1177 (2013).
[Crossref]

Yeung, Y. Y.

H. F. Chow, C. W. Wan, K. H. Low, and Y. Y. Yeung, “A highly selective synthesis of diarylethynes and their oligomers by a palladium-catalyzed Sonogashira coupling reaction under phase transfer conditions,” J. Org. Chem. 66(5), 1910–1913 (2001).
[Crossref] [PubMed]

Youngblood, W. J.

I. C. Khoo, S. Webster, S. Kubo, W. J. Youngblood, J. D. Liou, T. E. Mallouk, P. Lin, D. J. Hagan, and S. E. W. Van, “Synthesis and characterization of the multi-photon absorption and excited-state properties of a neat liquid 4-propyl 4′-butyl diphenyl acetylene,” J. Mater. Chem. 19(40), 7525–7531 (2009).
[Crossref]

Yuki, A.

A. Yuki, K. Sungmin, N. Shunpei, S. Koichi, K. Susumu, W. Junji, and K. Genichi, “Synthesis of new wide nematic diaryl-diacetylenes containing thiophene-based heteromonocyclic and heterobicyclic structures, and their birefringence properties,” Liq. Cryst. 41(5), 642–651 (2014).
[Crossref]

Zhang, M.

M. Zhang, X. Guo, S. Zhang, and J. Hou, “Synergistic effect of fluorination on molecular energy level modulation in highly efficient photovoltaic polymers,” Adv. Mater. 26(7), 1118–1123 (2014).
[Crossref] [PubMed]

Zhang, S.

M. Zhang, X. Guo, S. Zhang, and J. Hou, “Synergistic effect of fluorination on molecular energy level modulation in highly efficient photovoltaic polymers,” Adv. Mater. 26(7), 1118–1123 (2014).
[Crossref] [PubMed]

Zhao, Y. H.

G. Y. Si, Y. H. Zhao, E. S. P. Leong, and Y. J. Liu, “Liquid-crystal-enabled active plasmonics: a review,” Materials (Basel) 7(2), 1296–1317 (2014).
[Crossref]

Zheng, Z.

Zhu, X.

S. Gauza, X. Zhu, K. Piecek, R. Dąbrowski, and S. T. Wu, “Fast switching liquid crystals for color-sequential LCDs,” J. Disp. Technol. 3(3), 250–252 (2007).
[Crossref]

Adv. Mater. (1)

M. Zhang, X. Guo, S. Zhang, and J. Hou, “Synergistic effect of fluorination on molecular energy level modulation in highly efficient photovoltaic polymers,” Adv. Mater. 26(7), 1118–1123 (2014).
[Crossref] [PubMed]

Angew. Chem. Int. Ed. Engl. (2)

L. Hunter, A. M. Z. Slawin, P. Kirsch, and D. O’Hagan, “Synthesis and conformation of multi-vicinal fluoroalkane diastereoisomers,” Angew. Chem. Int. Ed. Engl. 46(41), 7887–7890 (2007).
[Crossref] [PubMed]

T. Geelhaar, K. Griesar, and B. Reckmann, “125 years of liquid crystals--a scientific revolution in the home,” Angew. Chem. Int. Ed. Engl. 52(34), 8798–8809 (2013).
[Crossref] [PubMed]

Chem. J. Chinese Universities (1)

R. Chen, Z. W. An, X. B. Chen, and P. Chen, “Syntheses and properties of four-ring liquid crystals with ethylene and internal alkyne bridge,” Chem. J. Chinese Universities 35(7), 1433–1438 (2014).

Chem. Soc. Rev. (1)

M. Hird, “Fluorinated liquid crystals--properties and applications,” Chem. Soc. Rev. 36(12), 2070–2095 (2007).
[Crossref] [PubMed]

Crystals (1)

R. Dąbrowski, P. Kula, and J. Herman, “High birefringence liquid crystals,” Crystals 3(3), 443–482 (2013).
[Crossref]

J. Appl. Phys. (1)

S. T. Wu, E. Ramos, and U. Finkenzeller, “Polarized UV spectroscopy of conjugated liquid crystals,” J. Appl. Phys. 68(1), 78–85 (1990).
[Crossref]

J. Disp. Technol. (1)

S. Gauza, X. Zhu, K. Piecek, R. Dąbrowski, and S. T. Wu, “Fast switching liquid crystals for color-sequential LCDs,” J. Disp. Technol. 3(3), 250–252 (2007).
[Crossref]

J. Mater. Chem. (1)

I. C. Khoo, S. Webster, S. Kubo, W. J. Youngblood, J. D. Liou, T. E. Mallouk, P. Lin, D. J. Hagan, and S. E. W. Van, “Synthesis and characterization of the multi-photon absorption and excited-state properties of a neat liquid 4-propyl 4′-butyl diphenyl acetylene,” J. Mater. Chem. 19(40), 7525–7531 (2009).
[Crossref]

J. Mater. Chem. C Mater. Opt. Electron. Devices (1)

R. Chen, Y. Jiang, J. Li, Z. An, X. Chen, and P. Chen, “Dielectric and optical anisotropy enhanced by 1,3-dioxolane terminal substitution on tolane-liquid crystals,” J. Mater. Chem. C Mater. Opt. Electron. Devices 3(33), 8706–8711 (2015).
[Crossref]

J. Org. Chem. (1)

H. F. Chow, C. W. Wan, K. H. Low, and Y. Y. Yeung, “A highly selective synthesis of diarylethynes and their oligomers by a palladium-catalyzed Sonogashira coupling reaction under phase transfer conditions,” J. Org. Chem. 66(5), 1910–1913 (2001).
[Crossref] [PubMed]

Journal of the SID (1)

S. Gauza, C. H. Wen, B. Wu, S. T. Wu, A. Spadlo, and R. Dąbrowski, “Fast-response nematic liquid-crystal mixtures,” Journal of the SID 14(3), 241–246 (2006).

Jpn. J. Appl. Phys. (1)

S. Gauza, C. H. Wen, B. J. Tan, and S. T. Wu, “UV stable high birefringence liquid crystals,” Jpn. J. Appl. Phys. 43(10), 7176–7180 (2004).
[Crossref]

Liq. Cryst. (3)

Y. M. Liao, H. L. Chen, C. S. Hsu, S. Gauza, and S. T. Wu, “Synthesis and mesomorphic properties of super high birefringence isothiocyanato bistolane liquid crystals,” Liq. Cryst. 34(4), 507–517 (2007).
[Crossref]

C. H. Wen, S. Gauza, and S. T. Wu, “Ultraviolet stability of liquid crystals containing cyano and isothiocyanato terminal groups,” Liq. Cryst. 31(11), 1479–1485 (2004).
[Crossref]

A. Yuki, K. Sungmin, N. Shunpei, S. Koichi, K. Susumu, W. Junji, and K. Genichi, “Synthesis of new wide nematic diaryl-diacetylenes containing thiophene-based heteromonocyclic and heterobicyclic structures, and their birefringence properties,” Liq. Cryst. 41(5), 642–651 (2014).
[Crossref]

Materials (Basel) (1)

G. Y. Si, Y. H. Zhao, E. S. P. Leong, and Y. J. Liu, “Liquid-crystal-enabled active plasmonics: a review,” Materials (Basel) 7(2), 1296–1317 (2014).
[Crossref]

Mol. Cryst. Liq. Cryst. (Phila. Pa.) (1)

P. T. Lin, S. T. Wu, C. Y. Chang, and C. S. Hsu, “UV stability of high birefringence liquid crystals,” Mol. Cryst. Liq. Cryst. (Phila. Pa.) 411(1), 1285–1295 (2004).
[Crossref]

Opt. Mater. Express (4)

Phase Transit. (1)

P. L. Praveen and P. O. Durga, “Effect of substituent on UV-visible absorption and photostability of liquid crystals: DFT study,” Phase Transit. 87(5), 515–525 (2014).
[Crossref]

Proc. SPIE (1)

S. Gauza, C. H. Wen, S. T. Wu, R. Dąbrowski, C. S. Hsu, C. O. Catanescu, and L. C. Chien, “High birefringence liquid crystals for photonic applications,” Proc. SPIE 5947, 594706 (2005).
[Crossref]

Soft Matter (1)

B. Li, W. He, L. Wang, X. Xiao, and H. Yang, “Effect of lateral fluoro substituents of rodlike tolane cyano mesogens on blue phase temperature ranges,” Soft Matter 9(4), 1172–1177 (2013).
[Crossref]

Other (3)

N. Vieweg, C. Jansen, and M. Koch, “Liquid Crystals and their Applications in the THz Frequency Range,” in Terahertz Spectroscopy and Imaging, K.-E. Peiponen et al, eds. (Berlin, 2013), pp. 301—326.

S. T. Wu, “Molecular design strategies for high birefringence liquid crystals,” MRS. Symposium Proceedings 709, 219–228 (2002).

S. T. Wu and D. K. Yang, Reflective Liquid Crystal Displays (Wiley-SID, 2001).

Supplementary Material (1)

NameDescription
» Data File 1: CSV (1 KB)      Phase transition temperatures (T/ oC) and associated transition enthalpy values (kJ mol-1) in parentheses for compounds 3Fn and 4Fn.

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Figures (8)

Fig. 1
Fig. 1 Chemical structures of the compounds used in this study.
Fig. 2
Fig. 2 The mesophase range of target compounds during heating. Cr: crystal; S: smectic A phase interval; N: nematic phase interval. See Data File 1 for underlying values.
Fig. 3
Fig. 3 DSC traces of compound 3-2 (A) and 3F2 (B) in the heating process before and after the 30 minutes of UV illumination. DSC traces of compound 3-2 (C) and 3F2 (D) in the heating process before and after the 240 minutes of UV illumination.
Fig. 4
Fig. 4 UV-vis absorption spectra (2 × 10−4 mol/L) and FL spectra (8 × 10−7 mol/L) of 3-2 (A, C) and 3F2 (B, D) in cyclohexane solution before and after the 240 minutes of UV illumination.
Fig. 5
Fig. 5 POM images ( × 200): Thread-like textures of nematic mesophases of 3-2 (A) and 3F2 (C); Schlieren textures of nematic mesophases of 3-2 (B) and 3F2 (D) after the 240 minutes of UV illumination.
Fig. 6
Fig. 6 (a) The possible products of PTP after UV exposure. (b) TGA curve of PTP in the n-heptane solution before and after 12h UV exposure.
Fig. 7
Fig. 7 The selected region of the 1H NMR (a) and whole 13C NMR (c) spectra of PTP before and after 4h UV exposure; The simulated 13C NMR (b) spectrum of structure 7; The selected region of the 13C NMR (d) spectrum of PTP after 4h UV exposure.
Fig. 8
Fig. 8 A resonance structure in fluorinated tolane-liquid crystals.

Tables (1)

Tables Icon

Table 1 The birefringences a and DFT calculated principal components (αXX, αYY, αZZ), isotropic component αb, anisotropy Δαc, triple bond length (l) of molecules 3-2 and 3F2. d

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