Large polycyclic aromatic hydrocarbons: Synthesis and discotic organization

References

1 J. C. Fetzer. The Chemistry and Analysis of the Large Polycyclic Aromatic Hydrocarbons, John Wiley, New York (2000).Search in Google Scholar

2 10.1002/cber.19640970226, K. F. Lang, J. Kalowy, H. Buffleb. Chem. Ber. Recl.97, 494 (1964).Search in Google Scholar

3 10.1002/cber.19620950438, K. F. Lang, J. Kalowy, H. Buffleb. Chem. Ber. Recl.95, 1052 (1962).Search in Google Scholar

4 10.1038/380227a0, D. J. Cook, S. Schlemmer, N. Balucani, D. R. Wagner, B. Steiner, R. J. Saykally. Nature380, 227 (1996).Search in Google Scholar PubMed

5 10.1002/jlac.19123940202, R. Scholl, C. Seer. Justus Liebigs Ann. Chem.394, 111 (1912).Search in Google Scholar

6 10.1002/cber.19110440210, R. Scholl, C. Seer. Ber. Dtsch. Chem. Ges.44, 1233 (1911).Search in Google Scholar

7 E. Clar. Ber. Dtsch. Chem. Ges.62, 1574 (1929).10.1002/cber.19290620633Search in Google Scholar

8 E. Clar. Polycyclic Hydrocarbons, Vols. 1 and 2, John Wiley, New York (1964).10.1007/978-3-662-01665-7Search in Google Scholar

9 10.1039/jr9580001577, E. Clar, M. Zander. J. Chem. Soc. 1577 (1958).Search in Google Scholar

10 M. Zander. Handbook of Polycyclic Aromatic Hydrocarbons, Marcel Dekker, New York (1983).Search in Google Scholar

11 S. Hagen, H. Hopf. Top. Curr. Chem.196, 44 (1998).Search in Google Scholar

12 10.1021/cr0103221, P. V. R. Schleyer. Chem. Rev.101, 1115 (2001).Search in Google Scholar PubMed

13 T. A. Skotheim, R. L. Elsenbaumer, J. R. Reynolds (Eds.). Handbook of Conducting Polymers, 2nd ed., Marcel Dekker, New York (1998).Search in Google Scholar

14 10.1021/cr990322p, M. Watson, A. Fechtenkötter, K. Müllen. Chem. Rev.101, 1267 (2001).Search in Google Scholar PubMed

15 10.1021/cr068010r, J. Wu, W. Pisula, K. Müllen. Chem. Rev.107, 718 (2007).Search in Google Scholar

16 10.1002/anie.200604203, S. Laschat, A. Baro, N. Steinke, F. Giesselmann, C. Hagele, G. Scalia, R. Judele, E. Kapatsina, S. Sauer, A. Schreivogel, M. Tosoni. Angew. Chem., Int. Ed.46, 4837 (2007).Search in Google Scholar

17 10.1126/science.1097789, J. P. Hill, W. Jin, A. Kosaka, T. Fukushima, H. Ichihara, T. Shimomura, K. Ito, T. Hashizume, N. Ishii, T. Aida. Science304, 1481 (2004).Search in Google Scholar

18 10.1126/science.1134441, Y. Yamamoto, T. Fukushima, Y. Suna, N. Ishii, A. Saeki, S. Seki, S. Tagawa, M. Taniguchi, T. Kawai, T. Aida. Science314, 1761 (2006).Search in Google Scholar

19 10.1021/ja0642360, S. Xiao, J. Tang, T. Beetz, X. Guo, N. Tremblay, T. Siegrist, Y. Zhu, M. Steigerwald, C. Nuckolls. J. Am. Chem. Soc.128, 10700 (2006).Search in Google Scholar

20 10.1021/jo0709807, C. P. Benard, Z. Geng, M. A. Heuft, K. VanCrey, A. G. Fallis. J. Org. Chem.72, 7229 (2007).Search in Google Scholar

21 M. Müller, J. Petersen, R. Strohmaier, C. Günther, N. Karl, K. Müllen. Angew. Chem., Int. Ed.35, 886 (1996).Search in Google Scholar

22 10.1002/(SICI)1521-3765(19981102)4:11<2099::AID-CHEM2099>3.0.CO;2-T, M. Müller, C. Kübel, K. Müllen. Chem.—Eur. J.4, 2099 (1998).Search in Google Scholar

23 10.1021/jo051418o, M. C. Bonifacio, C. R. Robertson, J. Y. Jung, B. T. King. J. Org. Chem.70, 8522 (2005).Search in Google Scholar

24 10.1021/ol048668w, A. Iuliano, P. Piccioli, D. Fabbri. Org. Lett.6, 3711 (2004).Search in Google Scholar

25 10.1002/anie.200504150, S. K. Collins, A. Grandbois, M. P. Vachon, J. Cote. Angew. Chem., Int. Ed.45, 2923 (2006).Search in Google Scholar

26 10.1021/ja038254i, P. M. Donovan, L. T. Scott. J. Am. Chem. Soc.126, 3108 (2004).Search in Google Scholar

27 10.1021/jo0512599, H. C. Shen, J. M. Tang, H. K. Chang, C. W. Yang, R. S. Liu. J. Org. Chem.70, 10113 (2005).Search in Google Scholar

28 10.1021/ja00096a056, M. B. Goldfinger, T. M. Swager. J. Am. Chem. Soc.116, 7985 (1994).Search in Google Scholar

29 10.1021/ja9642673, M. B. Goldfinger, K. B. Crawford, T. M. Swager. J. Am. Chem. Soc.119, 4578 (1997).Search in Google Scholar

30 10.1021/jo050104y, T. Yao, M. A. Campo, R. C. Larock. J. Org. Chem.70, 3511 (2005).Search in Google Scholar

31 10.1016/S0040-4039(00)92350-5, R. D. Bronene, F. Diederich. Tetrahedron Lett.32, 5227 (1991).Search in Google Scholar

32 10.1007/BFb0048505, K. A. Muszkat. Top. Curr. Chem.88, 89 (1981).Search in Google Scholar

33 H. Meier. Angew. Chem., Int. Ed.31, 1399 (1992).Search in Google Scholar

34 10.1002/anie.200502142, S. X. Xiao, M. Myers, Q. Miao, S. Sanaur, K. L. Pang, M. L. Steigerwald, C. Nuckolls. Angew. Chem., Int. Ed.44, 7390 (2005).Search in Google Scholar PubMed

35 10.1021/ja972019g, L. T. Scott, P. C. Cheng, M. M. Hashemi, M. S. Bratcher, D. T. Meyer, H. B. Warren. J. Am. Chem. Soc.119, 10963 (1997).Search in Google Scholar

36 10.1021/ja00018a082, L. T. Scott, M. M. Hashemi, D. T. Meyer, H. B. Warren. J. Am. Chem. Soc.113, 7082 (1991).Search in Google Scholar

37 10.1126/science.1068427, L. T. Scott, M. M. Boorum, B. J. McMahon, S. Hagen, J. Mack, J. Blank, H. Wegner, A. de Meijere. Science295, 1500 (2002).Search in Google Scholar PubMed

38 10.1126/science.1064250, M. M. Boorum, Y. V. Vasil’ev, T. Drewello, L. T. Scott. Science294, 828 (2001).Search in Google Scholar PubMed

39 10.1021/cr050553y, V. M. Tsefrikas, L. T. Scott. Chem. Rev.106, 4868 (2006).Search in Google Scholar PubMed

40 10.1021/ja046513d, P. Rempala, J. Kroulik, B. T. King. J. Am. Chem. Soc.126, 15002 (2004).Search in Google Scholar PubMed

41 10.1016/j.chemphys.2005.02.002, M. D. Stefano, F. Negri, P. Carbone, K. Müllen. Chem. Phys.314, 85 (2005).Search in Google Scholar

42 10.1002/asia.200700370, X. Yang, X. Dou, K. Müllen. Chem. Asia J.3, 759 (2008).Search in Google Scholar PubMed

43 X. Dou, W. Pisula, D. Wu, X. Feng, K. Müllen. Unpublished results.Search in Google Scholar

44 10.1021/ol053043z, X. L. Feng, J. Wu, V. Enkelmann, K. Müllen. Org. Lett.8, 1145 (2006).Search in Google Scholar PubMed

45 10.1002/anie.200605224, X. L. Feng, J. Wu, M. Ai, W. Pisula, L. Zhi, J. P. Rabe, K. Müllen. Angew. Chem., Int. Ed.46, 3033 (2007).Search in Google Scholar PubMed

46 10.1021/cm702592q, X. L. Feng, W. Pisula, M. Ai, S. Groper, J. P. Rabe, K. Müllen. Chem. Mater.20, 1191 (2008).Search in Google Scholar

47 10.1021/cm800515s, X. L. Feng, W. Pisula, M. Takase, V. Enkelmann, K. Müllen. Chem. Mater.20, 2872 (2008).Search in Google Scholar

48 10.1002/anie.200703967, X. L. Feng, W. Pisula, L. Zhi, M. Takase, K. Müllen. Angew. Chem., Int. Ed.47, 1703 (2008).Search in Google Scholar

49 10.1021/ja808979t, X. L. Feng, W. Pisula, T. Kudernac, D. Q. Wu, L. Zhi, S. De Feyter, K. Müllen. J. Am. Chem. Soc.131, 4439 (2009).Search in Google Scholar

50 10.1002/1521-3765(20020315)8:6<1424::AID-CHEM1424>3.0.CO;2-Z, C. D. Simpson, J. D. Brand, A. J. Berresheim, L. Przybilla, H. J. Rader, K. Müllen. Chem.—Eur. J.8, 1424 (2002).Search in Google Scholar

51 10.1021/ja000832x, F. Dötz, J. D. Brand, S. Ito, L. Gherghel, K. Müllen. J. Am. Chem. Soc.122, 7707 (2002).Search in Google Scholar

52 10.1002/anie.200352855, Z. Tomovic, M. Watson, K. Müllen. Angew. Chem., Int. Ed.43, 755 (2004).Search in Google Scholar

53 10.1021/ja710234t, X. Yang, X. Dou, A. Rouhanipour, L. Zhi, H. J. Räder, K. Müllen. J. Am. Chem. Soc.130, 4216 (2008).Search in Google Scholar

54 10.1021/ja00246a033, S. E. Stein, R. L. Brown. J. Am. Chem. Soc.109, 3721 (1987).Search in Google Scholar

55 10.1021/ja048580d, Z. H. Wang, Z. Tomovic, M. Kastler, R. Pretsch, F. Negri, V. Enkelmann, K. Müllen. J. Am. Chem. Soc.126, 7794 (2004).Search in Google Scholar

56 10.1021/ja062026h, M. Kastler, J. Schmidt, W. Pisula, D. Sebastiani, K. Müllen. J. Am. Chem. Soc.128, 9526 (2006).Search in Google Scholar

57 10.1021/ja075260w, X. Feng, W. Pisula, K. Müllen. J. Am. Chem. Soc.129, 14116 (2007).Search in Google Scholar

58 10.1002/anie.200701452, M. Takase, V. Enkelmann, D. Sebastiani, M. Baumgarten, K. Müllen. Angew. Chem., Int. Ed.46, 5524 (2007).Search in Google Scholar

59 10.1039/b506619k, S. Kumar. Chem. Soc. Rev.35, 83 (2006).Search in Google Scholar

60 10.1039/b417320c, S. Sergeyev, W. Pisula, Y. H. Geerts. Chem. Soc. Rev.36, 1902 (2007).Search in Google Scholar

61 10.1007/BF02846252, S. Chandrasekhar, B. K. Sadashiva, K. A. Suresh. Pramana9, 471 (1977).Search in Google Scholar

62 I. Dierking. Textures of Liquid Crystals, Wiley-VCH, Weinheim (2003).10.1002/3527602054Search in Google Scholar

63 10.1007/s12043-999-0136-2, V. S. K. Balagurusamy, S. K. Prasad, S. Chandrasekhar, S. Kumar, M. Manickam, C. V. Yelamaggad. Pramana53, 3 (1999).Search in Google Scholar

64 10.1080/10587259508033472, N. Boden, R. J. Bushby, A. N. Cammidge, J. Clements, R. Luo. Mol. Cryst. Liq. Cryst.261, 251 (1995).Search in Google Scholar

65 10.1002/adma.200502116, Y. Yamamoto, T. Fukushima, W. Jin, A. Kosaka, T. Hara, T. Nakamura, A. Saeki, S. Seki, S. Tagawa, T. Aida. Adv. Mater.18, 1297 (2006).Search in Google Scholar

66 A. M. van de Craats, J. M. Warman, A. Fechtenkötter, J. D. Brand, M. A. Harbison, K. Müllen. Adv. Mater.11, 1469 (1999).Search in Google Scholar

67 N. Boden, B. Movaghar. In Handbook of Liquid Crystals, Vol. 2B, D. Demus, J. Goodby, G. W. Gray, H. W. Spiess, V. Vill (Eds.), Chap. IX, Wiley-VCH, Weinheim (1998).Search in Google Scholar

68 10.1002/adma.200300009, M. O’Neill, S. M. Kelly. Adv. Mater.15, 1135 (2003).Search in Google Scholar

69 10.1002/(SICI)1099-1409(200001/02)4:1<88::AID-JPP208>3.0.CO;2-6, H. Eichorn. J. Porphyrins Phthalocyanines4, 88 (2000).Search in Google Scholar

70 10.1021/ja00190a041, B. A. Gregg, M. A. Fox, A. J. Bard. J. Am. Chem. Soc.111, 3024 (1989).Search in Google Scholar

71 10.1039/c39940000465, N. Bodon, R. J. Bushby, A. N. Cammidge. J. Chem. Soc., Chem. Commun. 465 (1994).Search in Google Scholar

72 10.1021/ja00108a009, N. Boden, R. J. Bushby, A. N. Cammidge. J. Am. Chem. Soc.117, 924 (1995).Search in Google Scholar

73 10.1021/ja00085a070, J. Zhang, J. S. Moore. J. Am. Chem. Soc.116, 2655 (1994).Search in Google Scholar

74 10.1002/1521-3773(20000703)39:13<2267::AID-ANIE2267>3.0.CO;2-7, S. Hoger, V. Enkelmann, K. Bonrad, C. Tschierske. Angew. Chem., Int. Ed.39, 2268 (2000).Search in Google Scholar

75 10.1002/(SICI)1521-3773(19980605)37:10<1434::AID-ANIE1434>3.0.CO;2-P, U. Rohr, P. Schlichting, A. Böhm, M. Gross, K. Meerholz, C. Bräuchle, K. Müllen. Angew. Chem., Int. Ed.37, 1434 (1998).Search in Google Scholar

76 C. Goltner, D. Pressner, K. Müllen, H. W. Spiess. Angew. Chem., Int. Ed.32, 1660 (1993).Search in Google Scholar

77 10.1021/ja016410k, B. A. Gregg, R. A. Cormier. J. Am. Chem. Soc.123, 7959 (2001).Search in Google Scholar

78 10.1021/ja00102a065, N. Boden, R. C. Borner, R. J. Bushby, J. Clements. J. Am. Chem. Soc.116, 10807 (1994).Search in Google Scholar

79 10.1021/cm050251c, W. Pisula, Z. Tomovic, C. Simpson, K. Kastler, T. Pakula, K. Müllen. Chem. Mater.17, 4296 (2005).Search in Google Scholar

80 10.1021/ja0548844, L. Piot, A. Marchenko, J. Wu, K. Müllen, D. Fichou. J. Am. Chem. Soc.127, 16245 (2005).Search in Google Scholar

81 10.1103/PhysRevLett.92.188303, F. Jackel, M. D. Watson, K. Müllen, J. P. Rabe. Phys. Rev. Lett.92, 188303 (2004).Search in Google Scholar PubMed

82 10.1007/s00339-008-4871-x, M. Ai, S. Groeper, W. Zhuang, X. Dou, X. Feng, K. Müllen, J. P. Rabe. Appl. Phys. A93, 277 (2008).Search in Google Scholar

83 10.1002/adma.200801428, L. Piot, C. Marie, X. Feng, K. Müllen, D. Fichou. Adv. Mater.20, 3854 (2008).Search in Google Scholar

84 10.1002/adma.200601437, M. Palma, J. Levin, V. Lemaur, A. Liscio, V. Palermo, J. Cornil, Y. Geerts, M. Lehmann, P. Samori. Adv. Mater.18, 3313 (2006).Search in Google Scholar

85 10.1021/cr030070z, J. M. Hoeben, P. Jonkheijm, E. W. Meijer, A. P. H. J. Schenning. Chem. Rev.105, 1491 (2005).Search in Google Scholar PubMed

86 H. N. Tsao, H. J. Rader, W. Pisula, A. Rouhanipour, K. Mullen. Phys. Status Solidi205, 421 (2008).10.1002/pssa.200723401Search in Google Scholar

87 10.1038/371141a0, D. Adam, P. Schuhmacher, J. Simmerer, L. Häussling, K. Siemensmeyer, K. H. Etzbach, H. Ringsdorf, D. Haarer. Nature371, 141 (1994).Search in Google Scholar

88 10.1021/jp071167i, W. Pisula, Z. Tomovic, M. D. Watson, K. Müllen, J. Kussmann, C. Ochsenfeld, T. Metzroth, J. Gauss. J. Phys. Chem. B111, 7481 (2007).Search in Google Scholar PubMed

89 10.1038/nmat2427, X. L. Feng, V. Marcon, W. Pisula, M. R. Hansen, J. Kirkpatrick, D. Andrienko, K. Kremer, K. Müllen. Nat. Mater.8, 421 (2009).Search in Google Scholar PubMed

90 10.1002/adma.200401171, W. Pisula, A. Menon, M. Stepputat, I. Lieberwirth, U. Kolb, A. Tracz, H. Sirringhaus, T. Pakula, K. Müllen. Adv. Mater.17, 684 (2005).Search in Google Scholar

91 10.1002/adma.200390114, A. M. van de Crass, N. Stutzmann, O. Bunk, M. M. Nielsen, M. D. Watson, K. Müllen, H. D. Chanzy, H. Sirringhaus, R. H. Friend. Adv. Mat.15, 495 (2003).Search in Google Scholar

92 10.1021/cr050149z, S. Gunes, H. Neugebauer, N. S. Saricifci. Chem. Rev.107, 1324 (2007).Search in Google Scholar

93 10.1126/science.293.5532.1119, L. Schmidt-Mende, A. Fechtenkotter, K. Müllen, E. Moons, R. H. Friend, J. D. MacKenzie. Science293, 1119 (2001).Search in Google Scholar

94 10.1002/adma.200800642, X. Feng, M. Liu, W. Pisula, M. Takase, J. Li, K. Müllen. Adv. Mater.20, 2684 (2008).Search in Google Scholar

95 10.1002/adma.19970090305, T. Christ, B. Glüsen, A. Greiner, A. Kettner, R. Sander, V. Stümpflen, V. Tsukruk, J. H. Wendorff. Adv. Mater.9, 48 (1997).Search in Google Scholar

96 10.1016/S0379-6779(98)00554-2, A. M. van de Craats, J. M. Warman, P. Schlichting, J. Rohr, Y. Geerts, K. Müllen. Synth. Met.102, 1550 (1999).Search in Google Scholar

97 10.1021/ma981595+, A. Bacher, C. H. Erdelen, W. Paulus, H. Ringsdorf, H. W. Schmidt, P. Schuhmacher. Macromolecules32, 4551 (1999).Search in Google Scholar