Synthesis of functionalized triphenylene discotic liquid crystals and the influence of unsaturated periphery on mesomorphism

Science China Chemistry

Volumn 54, Issue 10, 2011, Pages 1576-1583

  Zhao, KeQing ^a   Zhou, Hui ^a   Yu, WenHao ^a   Hu, Ping ^a   Wang, BiQin ^a   Monobe, Hirosato ^b   Shimizu, Yo ^b  

^a SICHUAN NORMAL UNIVERSITY   (China)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

discotic liquid crystal; functional periphery; hexagonal columnar mesophase; mesomorphism engineering; triphenylene

Indexed keywords

COLUMNAR MESOPHASES; DISCOTIC LIQUID CRYSTAL; FUNCTIONAL PERIPHERY; MESOMORPHISM ENGINEERING; TRIPHENYLENES;

ACETYLENE; DIFFERENTIAL SCANNING CALORIMETRY; OLEFINS; OPTICAL MICROSCOPY; THERMOTROPIC LIQUID CRYSTALS; X RAY DIFFRACTION ANALYSIS;

LIQUIDS;

EID: 80755128247     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-011-4325-8     Document Type: Article

References (43)

1. S. Kumar 2006 Self-organization of disc-like molecules: Chemical aspects Chem Soc Rev 35 83 109 10.1039/b506619k 1:CAS:528:DC%2BD2MXhtlantbnP (Pubitemid 43485015)
2. D. Perez E. Guitian 2004 Selected strategies for the synthesis of triphenylenes Chem Soc Rev 33 274 283 10.1039/b305549n 1:CAS:528: DC%2BD2cXks1Chsrk%3D (Pubitemid 38952416)
3. M.D. Watson A. Fechtenkotter K. Mullen 2001 Big is beautiful- "Aromaticity" revisited from the viewpoint of macromolecular and supramolecular benzene chemistry Chem Rev 101 1267 1300 10.1021/cr990322p 1:CAS:528:DC%2BD3MXisl2rs7Y%3D (Pubitemid 35375209)
4. 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 10.1002/anie.200604203 1:CAS:528:DC%2BD2sXnsFyrtbk%3D (Pubitemid 47055951)
5. S. Sergeyev W. Pisula Y.H. Geerts 2007 Discotic liquid crystals: A new generation of organic semiconductors Chem Soc Rev 36 1902 1929 10.1039/b417320c 1:CAS:528:DC%2BD2sXht1GhtbzJ
6. Y. Shimizu K. Oikawa K. Nakayama D. Guillon 2007 Mesophase semiconductors in field effect transistors J Mater Chem 17 4223 4229 10.1039/b705534j 1:CAS:528:DC%2BD2sXhtFCktrnI (Pubitemid 47585229)
7. L.L. Li P. Hu B.Q. Wang W.H. Yu Y. Shimizu K.Q. Zhao 2010 Synthesis and mesomorphism of ether-ester mixed tail C3-symmetrical truxene discotic liquid crystals Liquid Cryst 37 499 506 10.1080/02678290903215337
8. Zhao KQ, Chen C, Monobe H, Hu P, Wang B, Shimizu Y. Threechain truxene discotic liquid crystal showing high charged carrier mobility. Chem Commun, 2011, 47, 6290-6292
9. R.J. Bushby O.R. Lozman 2002 Discotic liquid crystals 25 years on Curr Opin Colloid Interf Sci 7 343 354 10.1016/S1359-0294(02)00085-7 1:CAS:528:DC%2BD38XpsFCjtr4%3D (Pubitemid 36007982)
10. F.J.M. Hoeben P. Jonkheijm E.W. Meijer A.P.H.J. Schenning 2005 About supramolecular assemblies of pi-conjugated systems Chem Rev 105 1491 1546 10.1021/cr030070z 1:CAS:528:DC%2BD2MXitVyntrg%3D (Pubitemid 40600882)
11. K.Q. Zhao W.H. Yu B.Q. Wang P. Hu 2009 Research progress in amide group hydrogen-bonding stabilized discotic liquid crystals J Sichuan Normal Univ (Natural Science) (in Chinese) 32 118 133 1:CAS:528:DC%2BD1MXjvFOru7o%3D
12. M. O'Neill S.M. Kelly 2011 Ordered materials for organic electronics and photonics Adv Mater 23 566 584 10.1002/adma.201002884
13. H. Eichhorn 2000 Mesomorphic phthalocycanines, tetraazaporphyrins, porphyrins and triphenylenes as charged-transporting materials J Porphyrins Phthalocyanines 4 88 102 10.1002/(SICI)1099-1409(200001/02)4:1<88::AID- JPP208>3.0.CO;2-6 1:CAS:528:DC%2BD3cXntVeksg%3D%3D
14. R.J. Bushby O.R. Lozman 2002 Photoconducting liquid crystals Curr Opin Solid State Mater Sci 6 569 578 10.1016/S1359-0286(03)00007-X 1:CAS:528:DC%2BD3sXktVKgtbk%3D (Pubitemid 36695929)
15. D. Adam P. Schuhmacher J. Simmerer L. Haussling K. Siemensmeyer K.H. Etzbach H. Ringsdorf D. Haarer 1994 Fast photoconduction in the highly ordered columnar phase of a discotic liquid crystal Nature 371 141 143 10.1038/371141a0 1:CAS:528:DyaK2MXns1Shsg%3D%3D (Pubitemid 24285063)
16. X. Feng V. Marcon W. Pisula M.R. Hansen J. Kirkpatrick F. Grozema D. Andrienko K. Kremer K. Müllen 2009 Towards high charge-carrier mobilities by rational design of the shape and periphery of discotics Nature Mater 8 421 426 10.1038/nmat2427 1:CAS:528:DC%2BD1MXkvVGrsL4%3D
17. L. Schmidt-Mende A. Fechtenkotter K. Mullen E. Moons R.H. Friend J.D. MacKenzie 2001 Self-organized discotic liquid crystals for high-efficiency organic photovoltaics Science 293 1119 1122 10.1126/science.293.5532.1119 1:CAS:528:DC%2BD3MXmtVWrtrs%3D (Pubitemid 32758088)
18. S. Kumar 2004 Recent developments in the chemistry of triphenylenebased discotic liquid crystals Liquid Cryst 31 1037 1059 10.1080/02678290410001724746 1:CAS:528:DC%2BD2cXlvVKlsbs%3D
19. S. Kumar 2005 Triphenylene-based discotic liquid crystal dimers, oligomers and polymers Liquid Cryst 32 1089 1113 10.1080/02678290500117415 1:CAS:528:DC%2BD2MXht1Sktb7K
20. L. Zhang H. Gopee D.L. Hughes A.N. Cammidge 2010 Antiaromatic twinned triphenylene discotics showing nematic phases and 2-dimensional π-overlap in the solid state Chem Commun 46 4255 4257 10.1039/c0cc00311e 1:CAS:528: DC%2BC3cXntVent74%3D
21. M. Kaller C. Deck A. Meister G. Hause A. Baro S. Laschate 2010 Counterion effects on the columnar mesophases of triphenylene-substituted [18]crown-6 ethers: Is flatter better? Chem Eur J 16 6326 6337 10.1002/chem.201000155 1:CAS:528:DC%2BC3cXmvVGqtLs%3D
22. J. Li Z. He H. Gopee A.N. Cammidge 2010 Synthesis of crown ether-linked discotic triphenylenes Org Lett 12 472 475 10.1021/ol902637z 1:CAS:528:DC%2BC3cXhtFGjuw%3D%3D
23. Cammidge AN, Chausson C, Gopee H, Li J, Hughes DL. Probing the structural factors influencing columnar mesophase formation and stability in triphenylene discotics. Chem Commun, 2009, 7375-7377
24. A.N. Cammidge 2006 The effect of size and shape variation in discotic liquid crystals based on triphenylene cores Phil Trans R Soc A 364 2697 2708 10.1098/rsta.2006.1847 1:CAS:528:DC%2BD28Xht1ymsLfM (Pubitemid 44661780)
25. A.N. Cammidge H. Gopee 2009 Synthesis and liquid crystal properties of mixed alkynyl-alkoxy-triphenylenes Liquid Cryst 36 809 816 10.1080/ 02678290903063000 1:CAS:528:DC%2BD1MXhtV2gsrrL
26. J. Miao L. Zhu 2010 Hydrogen bond-assisted supramolecular self-assembly of doubly discotic supermolecules based on porphyrin and triphenylene Chem Mater 22 197 206 10.1021/cm902731u 1:CAS:528:DC%2BD1MXhsV2htb7K
27. W.H. Yu K.Q. Zhao B.Q. Wang P. Hu 2007 Synthesis and mesomorphism of hydrogen-bonding stabilized triphenylene discotic liquid crystals Acta Chim Sinica (in Chinese) 65 1140 1148 1:CAS:528:DC%2BD2sXnvFCkurg%3D
28. K.Q. Zhao C.Y. Gao P. Hu B.Q. Wang Q. Li 2006 Synthesis of triphenylene discotic liquid crystals substituted with ester or amide functional groups and the effect of hydrogen bonding on mesogenic behaviors Acta Chim Sinica (in Chinese) 64 1051 1062 1:CAS:528:DC%2BD28XlsVOgu74%3D (Pubitemid 44663001)
29. Y. Miyake P. Hu K.Q. Zhao H. Monobe A. Fujii M. Ozaki Y. Shimizu 2010 Carrier mobility behavior of triphenylene mesogen with a hydrogen bonding amide group Mol Cryst Liquid Cryst 525 97 103 10.1080/15421401003796074 1:CAS:528:DC%2BC3cXovVKlurw%3D
30. S.J. Mahoney M.M. Ahmida H. Kayal N. Fox Y. Shimizu S.H. Eichhorn 2009 Synthesis, mesomorphism and electronic properties of nonaflate and cyano-substituted pentyloxy and 3-methylbutyloxy triphenylenes J Mater Chem 19 9221 9232 10.1039/b914290h 1:CAS:528:DC%2BD1MXhsFSgtrjK
31. H.M. Chen K.Q. Zhao L. Wang P. Hu B.Q. Wang 2011 Synthesis and mesomorphism of triphenylene discotic liquid crystals containing fluorinated chains Soft Mater 9 359 381 10.1080/1539445X.2010.525444 1:CAS:528: DC%2BC3MXltl2rs7o%3D
32. G.F. Yang K.Q. Zhao W.H. Yu P. Hu B.Q. Wang 2009 Synthesis of unsymmetric triphenylene discotic liquid crystals with a semi-fluorinated chain and the influence of fluorophobic effect on mesogenic behavior Sci China Ser B: Chem 52 8 1244 1252 10.1007/s11426-009-0113-0 1:CAS:528:DC%2BD1MXptFCku7w%3D
33. W. Yu S.C. Nie Y.F. Bai Y. Jing B.Q. Wang P. Hu K.Q. Zhao 2010 Synthesis of disk-rod-disk liquid crystal trimers by using click chemistry Sci China Chem 53 5 1134 1141 10.1007/s11426-010-0140-x 1:CAS:528:DC%2BC3cXmslOhs70%3D
34. H. Ji K.Q. Zhao W.H. Yu B.Q. Wang P. Hu 2009 Synthesis and mesomorphism of diacetylene-bridged triphenylene discotic liquid crystal dimers Sci China Ser B: Chem 52 975 985 10.1007/s11426-009-0003-5 1:CAS:528:DC%2BD1MXnslSqsro%3D
35. C.M. 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 Polym Chem 46 2960 2974 10.1002/pola.22631 1:CAS:528: DC%2BD1cXltlWlsrk%3D (Pubitemid 351579049)
36. A.N. Cammidge A.R. Beddall H. Gopee 2007 Unexpected mesophase behaviour in novel triphenylene multi-alkenes Tetrahedron Lett 48 6700 6703 10.1016/j.tetlet.2007.07.097 1:CAS:528:DC%2BD2sXps1Wnurk%3D (Pubitemid 47287688)
37. Schulte JL, 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 (Pubitemid 128536296)
38. Y.F. Bai K.Q. Zhao P. Hu B.Q. Wang Y. Shimizu 2009 Synthesis of amide group containing triphenylene derivatives as discotic liquid crystals and organic gelators Mol Cryst Liquid Cryst 509 60 76 10.1080/15421400903112069
39. K.Q. Zhao B.Q. Wang P. Hu Q. Li L.F. Zhang 2005 Synthesis of new triphenylene-containing discotic liquid crystals and the influence of fluorophilic effect and molecular symmetry on mesomorphism Chin J Chem 23 6 767 774 10.1002/cjoc.200590767 1:CAS:528:DC%2BD2MXkvFClsro%3D (Pubitemid 40771844)
40. K.Q. Zhao B.Q. Wang P. Hu C.Y. Gao F.J. Yuan H.R. Li 2006 New triphenylene based discotic liquid crystals with mixed tails: molecular symmetry and wide columnar mesophase range Chin J Chem 24 210 214 10.1002/cjoc.200690040 1:CAS:528:DC%2BD28Xhtlaitrs%3D
41. K.Q. Zhao P. Hu B.Q. Wang W.H. Yu H.M. Chen X.L. Wang Y. Shimizu 2007 Synthesis of mixed tail triphenylene discotic liquid crystals: Molecular symmetry and oxygen-atom effect on stabilization of columnar mesophases Chin J Chem 25 375 381 10.1002/cjoc.200790072 1:CAS:528:DC%2BD2sXjsVCktb8%3D
42. Dierking I. Textures of Liquid Crystals. Weinheim: Wiley-VCH, 2003
43. F.J. Ding K.Q. Zhao 2009 Study on clear points of triphenylene discotic liquid crystals with vinyloxy peripheral chains by mean field theory Acta Chem Sinica (in Chinese) 67 2290 2294 1:CAS:528:DC%2BD1MXhsVKit7vO