New functionalised derivatives of hexaalkoxytriphenylene

Molecular Crystals and Liquid Crystals

Volumn 411, Issue , 2004, Pages

  Bushby, Richard J ^a   Liu, Quanying ^a   Lozman, Owen R ^a   Lu, Zhibao ^a   McLaren, Sholto R ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

Discotic liquid crystals; Functional materials; Substituted triphenylenes; Synthesis

Indexed keywords

CROWN ETHERS; DERIVATIVES; FULLERENES; SINGLE CRYSTALS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

DISCOTIC LIQUID CRYSTALS (DLC); FUNCTIONAL MATERIALS; HEXAALKOXYTRIPHENYLENE; SUBSTITUTED TRIPHENYLENES;

LIQUID CRYSTALS;

EID: 12844260793     PISSN: 15421406     EISSN: None     Source Type: Journal    
DOI: 10.1080/15421400490435288     Document Type: Conference Paper

References (33)

1. Cammidge, A. N. & Bushby, R. J. (1998). Synthesis and structural features of discotic liquid crystals. Handbook of Liquid Crystals, 2B, 693-748.
2. Boden, N., Bushby, R. J., & Clements, J. (1993). Mechanism of quasi-one-dimensional electronic conductivity in discotic liquid-crystals. J. Chem. Phys., 98, 5920-5931; Markovitsi, D., Germain, A., Millie, P., Lecuyer, P., Gallos, L. K., Argyrakis, P., Bengs, H., & Ringsdorf, H. (1995). Triphenylene columnar liquid-crystals-excited-states and energy-transfer. J. Phys. Chem., 99, 1006-1017; Simmerer, J., Glusen, B., Paulus, W., Kettner, A., Schuhmacher, P., Adam, D., Etzbach, K. H., Siemensmeyer, K., Wendorff, J. H., Ringsdorf, H., & Haarer, D. (1996). Transient photoconductivity in a discotic hexagonal plastic crystal. Adv. Mater., 8, 815.
3. Boden, N., Bushby, R. J., & Clements, J. (1993). Mechanism of quasi-one-dimensional electronic conductivity in discotic liquid-crystals. J. Chem. Phys., 98, 5920-5931; Markovitsi, D., Germain, A., Millie, P., Lecuyer, P., Gallos, L. K., Argyrakis, P., Bengs, H., & Ringsdorf, H. (1995). Triphenylene columnar liquid-crystals-excited-states and energy-transfer. J. Phys. Chem., 99, 1006-1017; Simmerer, J., Glusen, B., Paulus, W., Kettner, A., Schuhmacher, P., Adam, D., Etzbach, K. H., Siemensmeyer, K., Wendorff, J. H., Ringsdorf, H., & Haarer, D. (1996). Transient photoconductivity in a discotic hexagonal plastic crystal. Adv. Mater., 8, 815.
4. Boden, N., Bushby, R. J., & Clements, J. (1993). Mechanism of quasi-one-dimensional electronic conductivity in discotic liquid-crystals. J. Chem. Phys., 98, 5920-5931; Markovitsi, D., Germain, A., Millie, P., Lecuyer, P., Gallos, L. K., Argyrakis, P., Bengs, H., & Ringsdorf, H. (1995). Triphenylene columnar liquid-crystals-excited-states and energy-transfer. J. Phys. Chem., 99, 1006-1017; Simmerer, J., Glusen, B., Paulus, W., Kettner, A., Schuhmacher, P., Adam, D., Etzbach, K. H., Siemensmeyer, K., Wendorff, J. H., Ringsdorf, H., & Haarer, D. (1996). Transient photoconductivity in a discotic hexagonal plastic crystal. Adv. Mater., 8, 815.
5. Boden, N., Bushby, R. J., Cammidge, A. N., & Martin, P. S. (1995). Glass-forming discotic liquid-crystalline oligomers. J. Mater. Chem., 5, 1857-1860; Boden, N., Bushby, R. J., Cammidge, A. N., ElMansoury, A., Martin, P. S., & Lu, Z. B. (1999). The creation of long-lasting glassy columnar discotic liquid crystals using dimeric discogens. J. Mater. Chem., 9, 1391-1402;
6. Boden, N., Bushby, R. J., Cammidge, A. N., & Martin, P. S. (1995). Glass-forming discotic liquid-crystalline oligomers. J. Mater. Chem., 5, 1857-1860; Boden, N., Bushby, R. J., Cammidge, A. N., ElMansoury, A., Martin, P. S., & Lu, Z. B. (1999). The creation of long-lasting glassy columnar discotic liquid crystals using dimeric discogens. J. Mater. Chem., 9, 1391-1402;
7. Boden, N., Bushby, R. J., & Lu, Z. B., (1998). A rational synthesis of polyacrylates with discogenic side groups. Liq. Cryst., 25, 47-58; Boden, N., Bushby, R. J., & Cammidge, A. N. (1995). Triphenylene-based discotic-liquid-crystalline polymers - a universal, rational synthesis. J. Am. Chem. Soc., 117, 924-927; Boden, N., Bushby, R. J., Lu, Z. B., & Eichhorn, H. (1999). Discotic liquid crystalline block copolymers 1: Side-chain discotic liquid crystalline diblock copolymers. Mol. Cryst. Liq. Cryst., 332, 2791-2801; Boden, N., Bushby, R. J., Kichhorn, H., Lu, Z. B., Abeysekera, R., & Robardes, A. W. (1999). Discotic liquid crystalline block copolymers 2: Main-chain discotic liquid crystalline diblock and triblock copolymers. Mol. Cryst. Liq. Cryst., 332, 2803-2812; Boden, N., Bushby, R. J., Cammidge, A. N., & Headdock, G. (1995). Versatile synthesis of unsymmetrically substituted triphenylenes. Synthesis-Stuttgart, 31 -32.
8. Boden, N., Bushby, R. J., & Lu, Z. B., (1998). A rational synthesis of polyacrylates with discogenic side groups. Liq. Cryst., 25, 47-58; Boden, N., Bushby, R. J., & Cammidge, A. N. (1995). Triphenylene-based discotic-liquid-crystalline polymers - a universal, rational synthesis. J. Am. Chem. Soc., 117, 924-927; Boden, N., Bushby, R. J., Lu, Z. B., & Eichhorn, H. (1999). Discotic liquid crystalline block copolymers 1: Side-chain discotic liquid crystalline diblock copolymers. Mol. Cryst. Liq. Cryst., 332, 2791-2801; Boden, N., Bushby, R. J., Kichhorn, H., Lu, Z. B., Abeysekera, R., & Robardes, A. W. (1999). Discotic liquid crystalline block copolymers 2: Main-chain discotic liquid crystalline diblock and triblock copolymers. Mol. Cryst. Liq. Cryst., 332, 2803-2812; Boden, N., Bushby, R. J., Cammidge, A. N., & Headdock, G. (1995). Versatile synthesis of unsymmetrically substituted triphenylenes. Synthesis-Stuttgart, 31 -32.
9. Boden, N., Bushby, R. J., & Lu, Z. B., (1998). A rational synthesis of polyacrylates with discogenic side groups. Liq. Cryst., 25, 47-58; Boden, N., Bushby, R. J., & Cammidge, A. N. (1995). Triphenylene-based discotic-liquid-crystalline polymers - a universal, rational synthesis. J. Am. Chem. Soc., 117, 924-927; Boden, N., Bushby, R. J., Lu, Z. B., & Eichhorn, H. (1999). Discotic liquid crystalline block copolymers 1: Side-chain discotic liquid crystalline diblock copolymers. Mol. Cryst. Liq. Cryst., 332, 2791-2801; Boden, N., Bushby, R. J., Kichhorn, H., Lu, Z. B., Abeysekera, R., & Robardes, A. W. (1999). Discotic liquid crystalline block copolymers 2: Main-chain discotic liquid crystalline diblock and triblock copolymers. Mol. Cryst. Liq. Cryst., 332, 2803-2812; Boden, N., Bushby, R. J., Cammidge, A. N., & Headdock, G. (1995). Versatile synthesis of unsymmetrically substituted triphenylenes. Synthesis-Stuttgart, 31 -32.
10. Boden, N., Bushby, R. J., & Lu, Z. B., (1998). A rational synthesis of polyacrylates with discogenic side groups. Liq. Cryst., 25, 47-58; Boden, N., Bushby, R. J., & Cammidge, A. N. (1995). Triphenylene-based discotic-liquid-crystalline polymers - a universal, rational synthesis. J. Am. Chem. Soc., 117, 924-927; Boden, N., Bushby, R. J., Lu, Z. B., & Eichhorn, H. (1999). Discotic liquid crystalline block copolymers 1: Side-chain discotic liquid crystalline diblock copolymers. Mol. Cryst. Liq. Cryst., 332, 2791-2801; Boden, N., Bushby, R. J., Kichhorn, H., Lu, Z. B., Abeysekera, R., & Robardes, A. W. (1999). Discotic liquid crystalline block copolymers 2: Main-chain discotic liquid crystalline diblock and triblock copolymers. Mol. Cryst. Liq. Cryst., 332, 2803-2812; Boden, N., Bushby, R. J., Cammidge, A. N., & Headdock, G. (1995). Versatile synthesis of unsymmetrically substituted triphenylenes. Synthesis-Stuttgart, 31 -32.
11. Boden, N., Bushby, R. J., & Lu, Z. B., (1998). A rational synthesis of polyacrylates with discogenic side groups. Liq. Cryst., 25, 47-58; Boden, N., Bushby, R. J., & Cammidge, A. N. (1995). Triphenylene-based discotic-liquid-crystalline polymers - a universal, rational synthesis. J. Am. Chem. Soc., 117, 924-927; Boden, N., Bushby, R. J., Lu, Z. B., & Eichhorn, H. (1999). Discotic liquid crystalline block copolymers 1: Side-chain discotic liquid crystalline diblock copolymers. Mol. Cryst. Liq. Cryst., 332, 2791-2801; Boden, N., Bushby, R. J., Kichhorn, H., Lu, Z. B., Abeysekera, R., & Robardes, A. W. (1999). Discotic liquid crystalline block copolymers 2: Main-chain discotic liquid crystalline diblock and triblock copolymers. Mol. Cryst. Liq. Cryst., 332, 2803-2812; Boden, N., Bushby, R. J., Cammidge, A. N., & Headdock, G. (1995). Versatile synthesis of unsymmetrically substituted triphenylenes. Synthesis-Stuttgart, 31 -32.
12. Boden, N., Bushby, R. J., Cammidge, A. N., & Headdock, G. (1995). Novel discotic liquid crystals created by electrophilic aromatic substitution. J. Mater. Chem., 5, 2275-2281; Boden, N., Bushby, R. J., & Cammidge, A. N. (1995). Functionalization of discotic liquid-crystals by direct substitution into the discogen ring-alpha-nitration of triphenylene-based discogens. Liq. Cryst., 18, 673-676; Kumar, S. & Manickam, M. (1998). Novel unsynunetrical triphenylene discotic liquid crystals: First synthesis of 1,2,3,6,7,10,11- heptaalkoxytriphenylenes. J. Chem. Soc. Chem. Comm., 1427-1428.
13. Boden, N., Bushby, R. J., Cammidge, A. N., & Headdock, G. (1995). Novel discotic liquid crystals created by electrophilic aromatic substitution. J. Mater. Chem., 5, 2275-2281; Boden, N., Bushby, R. J., & Cammidge, A. N. (1995). Functionalization of discotic liquid-crystals by direct substitution into the discogen ring-alpha-nitration of triphenylene-based discogens. Liq. Cryst., 18, 673-676; Kumar, S. & Manickam, M. (1998). Novel unsynunetrical triphenylene discotic liquid crystals: First synthesis of 1,2,3,6,7,10,11- heptaalkoxytriphenylenes. J. Chem. Soc. Chem. Comm., 1427-1428.
14. Boden, N., Bushby, R. J., Cammidge, A. N., & Headdock, G. (1995). Novel discotic liquid crystals created by electrophilic aromatic substitution. J. Mater. Chem., 5, 2275-2281; Boden, N., Bushby, R. J., & Cammidge, A. N. (1995). Functionalization of discotic liquid-crystals by direct substitution into the discogen ring-alpha-nitration of triphenylene-based discogens. Liq. Cryst., 18, 673-676; Kumar, S. & Manickam, M. (1998). Novel unsynunetrical triphenylene discotic liquid crystals: First synthesis of 1,2,3,6,7,10,11- heptaalkoxytriphenylenes. J. Chem. Soc. Chem. Comm., 1427-1428.
15. Bushby, R. J., Boden, N., Kilner, C. A., Lozman, O. R., Lu, Z. B., Liu, Q., & Thorton-Pett, M. A. (2002). Helical geometry and liquid crystal properties of 2,3,6,7,10,11-hexaalkoxy-1-nitrotriphenylenes. J. Mater. Chem., Submitted for publication.
16. Borner, R. C. & Jackson, R. F. (1994). J. Chem. Soc. Chem. Comm., 7, 845-846; Cooke, G., Franeck, H., & Violini, S. (1997). Synthetic Commun., 27, 3745-3748; Stewart, D., McHattie, G. S., & Imrie, C. T. (1998). Convenient synthesis of a discotic side group liquid crystal polymer. J. Mater. Chem., 8, 47-51.
17. Borner, R. C. & Jackson, R. F. (1994). J. Chem. Soc. Chem. Comm., 7, 845-846; Cooke, G., Franeck, H., & Violini, S. (1997). Synthetic Commun., 27, 3745-3748; Stewart, D., McHattie, G. S., & Imrie, C. T. (1998). Convenient synthesis of a discotic side group liquid crystal polymer. J. Mater. Chem., 8, 47-51.
18. Borner, R. C. & Jackson, R. F. (1994). J. Chem. Soc. Chem. Comm., 7, 845-846; Cooke, G., Franeck, H., & Violini, S. (1997). Synthetic Commun., 27, 3745-3748; Stewart, D., McHattie, G. S., & Imrie, C. T. (1998). Convenient synthesis of a discotic side group liquid crystal polymer. J. Mater. Chem., 8, 47-51.
19. Boden, N., Bushby, R. J., Liu, Q. Y., & Lozman, O. R. (2001). CPI (complementary polytopic interaction) stabilised liquid crystal compounds formed by esters of 2-hydroxy-3,6,7,10,11-pentakis(hexyloxy)triphenylene. J. Mater. Chem., 11, 1612-1617.
20. Bushby, R. J. & Lu, Z. B. (2001). Isopropoxy as a masked hydroxy group in aryl oxidative coupling reactions. Synthesis-Stuttgart, 763-767.
21. Boden, N., Bushby, R. J., Lu, Z. B., & Lozman, O. R. (2001). CPI induction of liquid crystal behaviour in triphenylenes with a mixture of hydrophobic and hydrophilic side chains. Liq. Cryst., 28, 657-661.
22. Cooke, G., Kaushal, N., Boden, N., Bushby, R. J., Lu, Z. B., & Lozman, O. (2000). Synthesis of liquid crystalline anthraquinolyl-triphenylenes. Tetrahedron Lett., 41, 7955-7959.
23. Cooke, G., Radhi, A., Boden, N., Bushby, R. J., Lu, Z. B., Brown, S., & Heath, S. L. (2000). Synthesis and characterisation of tetrathiafulvalenyl- and ferrocenyl-triphenylenes. Tetrahedron, 56, 3385-3390.
24. Boden, N., Bushby, R. J., Cooke, G., Lozman, O. R., & Lu, Z. B. (2001). CPI: A recipe for improving applicable properties of discotic liquid crystals. J. Am. Chem. Soc., 123, 7915-7916.
25. Bushby, R. J., Liu, Q. Y., & Lozman, O. R., (2002). Unpublished results.
26. Chuard, T. & Deschenaux, R. (1996), First fullerene[60]-containing thermotropic liquid crystal-preliminary communication. Helv. Chim. Acta., 79, 736-741; Chuard, T., Dardel, B., Deschenaux, R., & Even, M. (2000), [60]Fullerene-containing thermotropic liquid crystals. Carbon, 38, 1573-1576; Chuard, T. & Deschenaux, R. (2002). Design, mesomorphic properties, and supramolecular organization of [60]fullerene-containing thermotropic liquid crystals. J. Mater. Chem., 12, 1944-1951.
27. Chuard, T. & Deschenaux, R. (1996), First fullerene[60]-containing thermotropic liquid crystal-preliminary communication. Helv. Chim. Acta., 79, 736-741; Chuard, T., Dardel, B., Deschenaux, R., & Even, M. (2000), [60]Fullerene-containing thermotropic liquid crystals. Carbon, 38, 1573-1576; Chuard, T. & Deschenaux, R. (2002). Design, mesomorphic properties, and supramolecular organization of [60]fullerene-containing thermotropic liquid crystals. J. Mater. Chem., 12, 1944-1951.
28. Chuard, T. & Deschenaux, R. (1996), First fullerene[60]-containing thermotropic liquid crystal-preliminary communication. Helv. Chim. Acta., 79, 736-741; Chuard, T., Dardel, B., Deschenaux, R., & Even, M. (2000), [60]Fullerene-containing thermotropic liquid crystals. Carbon, 38, 1573-1576; Chuard, T. & Deschenaux, R. (2002). Design, mesomorphic properties, and supramolecular organization of [60]fullerene-containing thermotropic liquid crystals. J. Mater. Chem., 12, 1944-1951.
29. Plehnert, R., Schroter, J. A., & Tschierske, C. (1998). Selective cationic binding at the air-water interface by thin films of rigid amphiphiles bearing laterally attached crown ether moieties. Langmuir, 14, 5245-5249; Schroter, J. A., Tschierske, C., Wittenberg, M., & Wendorff, J. H. (1997). Liquid-crystalline crown ether: Forming columnar mesophases by molecular recognition. Angew. Chem. Int. Edit., 96, 1119-1121; Ashton P. R., Joachimi, D., Spencer, N., Stoddart, J. F., Tschierske, C., White, A. J. P., Williams, D. J., & Zab, K. (1994). A new class of novel macrocyclic mesogens. Angew. Chem. Int. Edit., 33, 1503-1506.
30. Plehnert, R., Schroter, J. A., & Tschierske, C. (1998). Selective cationic binding at the air-water interface by thin films of rigid amphiphiles bearing laterally attached crown ether moieties. Langmuir, 14, 5245-5249; Schroter, J. A., Tschierske, C., Wittenberg, M., & Wendorff, J. H. (1997). Liquid-crystalline crown ether: Forming columnar mesophases by molecular recognition. Angew. Chem. Int. Edit., 96, 1119-1121; Ashton P. R., Joachimi, D., Spencer, N., Stoddart, J. F., Tschierske, C., White, A. J. P., Williams, D. J., & Zab, K. (1994). A new class of novel macrocyclic mesogens. Angew. Chem. Int. Edit., 33, 1503-1506.
31. Plehnert, R., Schroter, J. A., & Tschierske, C. (1998). Selective cationic binding at the air-water interface by thin films of rigid amphiphiles bearing laterally attached crown ether moieties. Langmuir, 14, 5245-5249; Schroter, J. A., Tschierske, C., Wittenberg, M., & Wendorff, J. H. (1997). Liquid-crystalline crown ether: Forming columnar mesophases by molecular recognition. Angew. Chem. Int. Edit., 96, 1119-1121; Ashton P. R., Joachimi, D., Spencer, N., Stoddart, J. F., Tschierske, C., White, A. J. P., Williams, D. J., & Zab, K. (1994). A new class of novel macrocyclic mesogens. Angew. Chem. Int. Edit., 33, 1503-1506.
32. Tschierske, C. (2001). Micro-segregation, molecular shape and molecular topology partners for the design of liquid crystalline materials with complex mesophase morphologies. J. Mater. Chem., 11, 2647-2671.
33. STO-31G basis set and B3YLP electron correlation.