Synthesis of unsymmetric triphenylene discotic liquid crystals with a semi-fluorinated chain and the influence of fluorophobic effect on mesogenic behavior

Science in China, Series B: Chemistry

Volumn 52, Issue 8, 2009, Pages 1244-1252

  Yang, Gaofan ^a   Zhao, Keqing ^a   Yu, Wenhao ^a   Hu, Ping ^a   Wang, Biqin ^a  

^a SICHUAN NORMAL UNIVERSITY   (China)

Author keywords

Columnar mesophase; Discotic liquid crystal; Fluorophobic effect; Molecular symmetry; Semi fluorinated ester chain; Triphenylene

Indexed keywords

COLUMNAR MESOPHASE; DISCOTIC LIQUID CRYSTAL; FLUOROPHOBIC EFFECT; MOLECULAR SYMMETRY; SEMI-FLUORINATED ESTER CHAIN; TRIPHENYLENE;

DIFFERENTIAL SCANNING CALORIMETRY; ESTERIFICATION; ESTERS; HYDROCARBONS; LIGHT SOURCES; LIQUID CRYSTALS; MELTING POINT; OPTICAL MICROSCOPY; STEELMAKING; SYNTHESIS (CHEMICAL); THERMOCHEMISTRY;

CRYSTAL SYMMETRY;

EID: 68649127608     PISSN: 10069291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-009-0113-0     Document Type: Article

References (42)

1. S. Laschat A. Baro N. Steinke F. Giesselmann C. Hägele G. Scalia R. Judele E. Kapatsina S. Sauer A. Schreivogel M. Tosoni 2007 Discotic liquid crystals: From tailor-made synthesis to plastic electronics Angew Chem Int Ed 46 4832 4887
2. S. Kumar 2004 Recent developments in the chemistry of triphenylenebased discotic liquid crystals Liq Cryst 31 1037 1059
3. H. X. Mao Z. Q. He C. X. Zhang 2006 Advances in the synthesis of triphenylene derivatives with flexible side chains (in Chinese) Chinese J Org Chem 26 413 418
4. D. Adam P. Schuhmacher J. Simmerer L. Häussling K. Siemensmeyer K. H. Etzbachi H. Ringsdorf D. Haarer 1994 Fast photoconduction in the highly ordered columnar phase of a discotic liquid crystal Nature 371 141 143
5. C. X. Zhang Z. Q. He J. J. Wang Y. S. Wang S. Ye 2008 Study of mesogenic properties and molecular conformation from a heterogeneous tetramer with a triphenylene centre core and three cyanobiphenyl tails J Mol Liq 138 93 99
6. X. Yu X. Z. Tang C. Y. Pan 2005 Synthesis, characterization and self-assembly behavior of six-armed star block copolymers with triphenylene core Polymer 46 11149 11156
7. C. X. Zhang Z. Q. He H. X. Mao J. J. Wang D. D. Wang Y. S. Wang Z. X. Li J. L. Pu 2007 Observation of disorder effects on charged carrier mobility in triphenylene-based discotic materials J Lumin 122 931 935
8. X. Yu J. Fu Y. C. Han C. Y. Pan 2003 AFM study of the self-assembly behavior of hexa-armed star polymers with a discotic triphenylene core Macromol Rapid Commun 24 742 747
9. S. Kumar M. Manickam 1999 First example of a functionalized triphenylene discotic trimer: molecular engineering of advanced materials Liq Cryst 26 939 941
10. J. Simmerer B. Glusen W. Paulus 1996 Transient photoconductivity in a discotic hexagonal plastic crystal Adv Mater 8 815 819
11. I. H. Stapff V. Stumpflen J. H. Wendorff D. B. Spohn D. Mobius 1997 Preliminary communication Multilayer light emitting diodes based on columnar discotics Liq Cryst 23 613 617
12. N. Boden R. J. Bushby J. Clements B. Movaghar 1999 Device applications of charge transport in discotic liquid crystals J Mater Chem 9 2081 2086
13. H. X. Mao Z. Q. He J. J. Wang C. X. Zhang P. Xie R. B. Zhang 2007 A discotic triphenylene dimer as organic hole transporting material for electroluminescence devices J Lumin 122 942 945
14. N. Boden R. J. Bushby P. S. Martin S. D. Evans R. W. Owens D. A. Smith 1999 Triphenylene-based discotic liquid crystals as self-assembled monolayers Langmuir 15 3790 3797
15. J. A. Rego S. Kumar H. Ringsdorf 1996 Synthesis and characterization of fluorescent, low-symmetry triphenylene discotic liquid crystals: Tailoring of mesomorphic and optical properties Chem Mater 8 1402 1409
16. S. Ishihara Y. Furuki S. Takeoka 2007 A hydrogen-bonded supramolecular hexagonal columnar liquid crystal composed of a tricarboxylic triphenylene and monopyridyl dendrons Chem Lett 36 282 283
17. U. Dahn C. Erdelen H. Ringsdorf R. Festag J. H. Wendorff P. A. Heney N. C. Maliszewskyj 1995 Fluoroalkylated discotic liquid crystals Liq Cryst 19 759 764
18. N. Terasawa H. Monobe K. Kiyohara Y. Shimizu 2003 Fluorination effect of the peripheral chains on the mesomorphic properties in discotic liquid crystals of hexasubstituted triphenylene Chem Lett 32 214 215
19. Terasawa N, Monobe H, Kiyohara K, Shimizu Y. Strong tendency towards homeotropic alignment in a hexagonal columnar mesophase of fluoroalkylated triphenylenes. Chem Commun, 2003, 1678-1679
20. N. Terasawa H. Monobe K. Kiyohara 2007 Mesomorphic properties of symmetrical and asymmetrical triphenylene homologues possessing fluoroalkylated side chains Liq Cryst 34 311 324
21. H. M. Chen K. Q. Zhao B. Q. Wang P. Hu 2007 Synthesis and mesomorphism of semi-fluorinated chain contained triphenylene discotic liquid crystals (in Chinese) Acta Chim Sinca 65 1368 1376
22. G. Cooke A. Radhi N. Boden R. J. Bushby Z. B. Lu S. Brown S. L. Heathc 2000 Synthesis and characterization of tetrathiafulvalenyl- and ferrocenyl-triphenylenes Tetrahedron 56 3385 3390
23. X. Yu Y. B. Chen C. Y. Pan Y. Di J. Y. Zhang 2005 Solid-state polymerization of 2,3,6,7,10,11-hexa(methacrylate) triphenylene J Polym Sci Part A: Polym Chem 43 1526 1534
24. C. Xing J. W. Y. Lam K. Q. Zhao B. Z. Tang 2008 Synthesis and liquid crystalline properties of poly(1-alkyne)s carrying triphenylene discogens J Polym Sci Part A: Polym Chem 46 2960 2974
25. B. Almandine O. F. Aebische W. Amrein B. Donnio R. Deschenaux D. Guillon C. Savary D. Scanu O. Scheidegger T. A. Jenny 2005 Mesomorphic hexabenzocoronenes bearing perfluorinated chains Chem Mater 17 4798 4807
26. M. Hird 2007 Fluorinated liquid crystals-Properties and applications Chem Soc Rev 36 2070 2095
27. F. B. Meng J. Lian Y. M. Gao 2008 Advances in fluorinated liquid crystals (in Chinese) Prog Chem 20 499 507
28. Y. G. Yang B. Q. Chen J. X. Wen 1999 Synthesis and mesomorphic properties of semi-perfluorinated chain liquid crystals Liq Cryst 26 893 896
29. B. Q. Chen J. X. Wen 1999 Synthesis and mesophase behaviour of mesogens bearing omega, alpha, alpha-trihydroperfluoroalkoxy end tails Liq Cryst 26 1135 1140
30. K. G. Liu H. F. Li Y. H. Shen K. Wang J. X. Wen 2001 Synthesis and characteristics of novel fluorinated steroidal liquid crystals Liq Cryst Displays 16 181 187
31. H. Kuwahara M. Hamada Y. Ishikawa T. Kunitake 1993 Self-organization of bilayer assemblies in a fluorocarbon medium J Am Chem Soc 115 3002 3003
32. G. Johansson V. Percec G. Ungar J. P. Zhou 1996 Fluorophobic effect in the self-assembly of polymers and model compounds containing tapered groups into supramolecular columns Macromolecules 29 646 660
33. V. Percec T. K. Bera 2002 Cell membrane as a model for the design of semifluorinated ion-selective nanostructured supramolecular systerms Tetrahedron 58 4031 4040 (Pubitemid 34465673)
34. T. M. Chapman R. Benrashid K. L. Gribbin J. P. Keener 1995 Determination of low critical surface energies of novel fluorinated poly (amide urethane) block copolymers. 1. Fluorinated side chains Macromolecules 28 331 335
35. F. Bracon F. Guittard E. T. D. Givenchy A. Cambon 1999 Highly fluorinated monomers precursors of side-chain liquid crystalline polysiloxanes J Polym Sci Part A: Polym Chem 37 4487 4496
36. M. Ragnoli E. Pucci M. Bertolucci B. Gallot G. Galli 2004 Effects of chemical variations on the mesophase behavior of new fluorinated poly(vinylcyclopropane)s J Fluorine Chem 125 283 292
37. F. X. You M. Y. Paik M. Häckel L. Kador D. Kropp H. W. Schmidt C. K. Ober 2005 Control and suppression of surface relief gratings in liquidcrystalline perfluoroalkyl-azobenzene polymers Adv Funct Mater 16 1577 1581
38. S. C. Chien H. H. Chen H. C. Chen Y. L. Yang H. F. Hsu T. L. Shih J. J. Lee 2007 Stable, low-temperature discotic nematic superstructures by incorporating a laterally substituted sidearm in hexakis(phenylethynyl)benzene discogens Adv Funct Mater 17 1896 1902
39. S. J. Cross J. W. Goodby A. W. Hall M. Hird S. M. Kelly K. J. Toyne C. Wu 1998 Unsymmetrical alkoxy-substituted triphenylenes: the dependence of mesomorphism on molecular shape Liq Cryst 28 1 11
40. Schulte J L, Laschat S, Vill V, Nishikawa E, Finkelmann H, Nimtz M. Convergent synthesis of columnar twins and tetramers from triphenylene building blocks-The first example of a columnar spiro-twin. Eur J Org Chem, 1998, 2499-2506
41. W. H. Yu K. Q. Zhao B. Q. Wang P. Hu 2007 Synthesis and mesomorphism of hydrogen-bonding stabilized triphenylene discotic liquid crystals (in Chinese) Acta Chim Sinca 65 1140 1148
42. P. Ioan D. Paul G. Marcel A. Posthumus T. M. Marcelis H. Zuilhof J. R. Sudhǒlter 2005 Asymmetry in liquid crystalline hexaalkoxy-triphenylene discotics Liq Cryst 32 977 983