Synthesis 2012; 44(12): 1928-1934
DOI: 10.1055/s-0031-1291010
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Alkyl-Substituted Tribenzopentaphenes as Versatile Polycondensed Aromatic Hydrocarbon π–π Stacking Building Blocks

Bassam Alameddine
a   Department of Mathematics and Natural Sciences, Gulf University for Science and Technology, Hawally 32093, Kuwait
,
Sofia Martin Caba
b   Chemistry Department, University of Fribourg, chemin du Musée 9, 1700 Fribourg, Switzerland, Fax: +41(26)3009739   Email: titus.jenny@unifr.ch
,
Mauro Schindler
b   Chemistry Department, University of Fribourg, chemin du Musée 9, 1700 Fribourg, Switzerland, Fax: +41(26)3009739   Email: titus.jenny@unifr.ch
,
Titus A. Jenny*
b   Chemistry Department, University of Fribourg, chemin du Musée 9, 1700 Fribourg, Switzerland, Fax: +41(26)3009739   Email: titus.jenny@unifr.ch
› Author Affiliations
Further Information

Publication History

Received: 29 December 2011

Accepted after revision: 12 April 2012

Publication Date:
14 May 2012 (online)


Abstract

We show the versatile synthesis of four tribenzopentaphene derivatives bearing alkyl side chains at three different positions. Substitutions on two of these positions led to subtle intensity changes at the lines of the blue emission, whereas alkylation in the bay region led to dimerization of the pentaphene derivative, resulting in a distortion of the chromophore geometry and an emission shift to green.

 
  • References

  • 1 Grimme S. Angew. Chem. Int. Ed. 2008; 47: 3430 ; and references therein
    • 2a Aebischer OF, Aebischer A, Donnio B, Alameddine B, Dadras M, Güdel H.-U, Guillon D, Jenny TA. J. Mater. Chem. 2007; 17: 1262
    • 2b Wu J, Li J, Kolbb U, Muellen K. Chem. Commun. 2006; 48
    • 2c Miao Q, Chi X, Xiao S, Zeis R, Lefenfeld M, Siegrist T, Steigerwald M, Nuckolls C. J. Am. Chem. Soc. 2006; 128: 1340
    • 2d Alameddine B, Aebischer OF, Amrein W, Donnio B, Deschenaux R, Guillon D, Savary C, Scanu D, Scheidegger O, Jenny TA. Chem. Mater. 2005; 17: 4798
    • 2e Bushby RJ, Lozman OR. Current Opinion in Colloid & Interface Science 2002; 7: 343
    • 2f O’Neill M, Kelly SM. Adv. Mater. (Weinheim, Ger.) 2003; 15: 1135
    • 2g Van de Craats A, Stutzman N, Bunk O, Nielsen MM, Watson M, Müllen K, Chanzy HD, Sirringhaus H, Friend RH. Adv. Mater. (Weinheim, Ger.) 2003; 15: 495
    • 3a Mori T, Kikuzawa Y, Takeuchi H. Org. Electron. 2008; 9: 328
    • 3b Hara T, Furukawa K, Nakamura T, Yamamoto Y, Kosaka A, Jin W, Fukushima T, Aida T. J. Phys. Soc. Jpn. 2008; 77: 34710
    • 3c Sergeyev S, Pisula W, Geerts YV. Chem. Soc. Rev. 2007; 36: 1902
    • 3d Lloyd MT, Mayer AC, Tayi AS, Bowen AM, Kasen TG, Herman DJ, Mourey DA, Anthony JE, Malliaras GC. Org. Electron. 2006; 7: 243
    • 3e Katz HE. Chem. Mater. 2004; 16: 4748
    • 3f Moon H, Zeis R, Borkent E.-J, Besnard C, Lovinger AJ, Siegrist T, Kloc C, Bao Z. J. Am. Chem. Soc. 2004; 126: 15322
    • 3g Xiao S, Tang J, Beetz T, Guo X, Tremblay N, Siegrist T, Zhu Y, Steigerwald M, Nuckolls C. J. Am. Chem. Soc. 2006; 128: 10700
    • 3h Pisula W, Menon A, Stepputat M, Lieberwirth I, Kolb U, Tracz A, Sirringhaus H, Pakula T, Muellen K. Adv. Mater. (Weinheim, Ger.) 2005; 17: 684
    • 3i Dimitrakopoulos CD, Malenfant PR. L. Adv. Mater. (Weinheim, Ger.) 2002; 14: 99
    • 3j Schmidt-Mende L, Fechtenchötter A, Müllen K, Moons E, Friend RH, MacKenzie JD. Science 2001; 293: 1119
    • 3k Xiao S, Myers M, Miao Q, Sanaur S, Pang K, Steigerwald M, Nuckolls C. Angew. Chem. Int. Ed. 2005; 44: 7390
    • 4a Konishi A, Hirao Y, Nakano M, Shimizu A, Botek E, Champagne B, Shiomi D, Sato K, Takui T, Matsumoto K, Kurata H, Kubo T. J. Am. Chem. Soc. 2010; 132: 11021
    • 4b Fogel Y, Zhi L, Rouhanipour A, Andrienko D, Joachim-Raeder H, Muellen K. Macromolecules 2009; 42: 6878
    • 4c Feng X, Pisula W, Ai M, Groeper S, Rabe JP, Muellen K. Chem. Mater. 2008; 20: 1191
    • 4d Feng X, Wu J, Ai M, Pisula W, Zhi L, Rabe JP, Muellen K. Angew. Chem. Int. Ed. 2007; 46: 3033
    • 4e Okamoto T, Senatore ML, Ling M.-M, Mallik AB, Tang ML, Bao Z. Adv. Mater. (Weinheim, Ger.) 2007; 19: 3381
    • 4f Terasawa N, Monobe H, Kiyohara K, Shimizu Y. Chem. Lett. 2003; 32: 214
    • 4g Lee M, Kim J.-W, Peleshanko S, Larson K, Yoo Y.-S, Vaknin D, Markutsya S, Tsukruk VV. J. Am. Chem. Soc. 2002; 124: 9121
    • 4h Yatabe T, Harbison MA, Brand JD, Wagner M, Müllen K, Samori P, Rabe JP. J. Mater. Chem. 2000; 10: 1519
    • 4i Henderson P, Ringsdorf H, Shuhmacher P. Liq. Cryst. 1995; 18: 191
    • 5a Feng X, Pisula W, Takase M, Dou X, Enkelmann V, Wagner M, Ding N, Muellen K. Chem. Mater. 2008; 20: 2872
    • 5b Chih-Wei C, Hong-Yi C, Shern-Long L, I-Jui H, Jey-Jau L, Chun-hsien C, Tien-Yau L. Macromolecules 2010; 43: 8741
    • 6a Fujiyama T, Toya Y, Nakatsuka M. Jpn. Kokai Tokkyo Koho JP 2008098357, 2008
    • 6b Nakatsuka M, Shimamura T, Ishida T, Totani Y. Jpn. Kokai Tokkyo Koho JP 2002359081, 2002
  • 8 Sauriat-Dorizon H, Maris T, Wuest JD, Enright GD. J. Org. Chem. 2003; 68: 240
    • 9a Hayashi T, Konishi M, Kobori Y, Kumada M, Higushi T, Hirotsu K. J. Am. Chem. Soc. 1984; 106: 158
    • 9b Bringmann S, Ahmed SA, Hartmann R, Mattay J. Synthesis 2011; 2291
  • 10 Kovacic P, Koch FW. J. Org. Chem. 1963; 28: 1864
    • 11a Zaugg H, Rapala RT, Leffler MT. J. Am. Chem. Soc. 1948; 70: 3224
    • 11b Yeo S.-J, Kim Y.-H, Lee D.-H, Jang H.-Y, Hong S.-K, Kim K.-K, Jeong D.-S. PCT Int. Appl. WO 2007105884, 2007
    • 11c Maly KE, Gagnon E, Maris T, Wuest JD. J. Am. Chem. Soc. 2007; 129: 4306
    • 11d Vives G, Rapenne G. Tetrahedron Lett. 2006; 47: 8741
    • 11e Watanabe S, Kido J. Chem. Lett. 2007; 36: 590
  • 12 Liaw BR, Huang WY, Huang PT, Chang MY, Han YK. Polymer 2007; 48: 7087
  • 13 Paquette LA, Moerck RE, Harirchian B, Magnus PD. J. Am. Chem. Soc. 1978; 100: 1597
    • 14a Kastler M, Pisula W, Wasserfallen D, Pakula T, Muellen K. J. Am. Chem. Soc. 2005; 127: 4286
    • 14b Harris KD, Xiao S, Lee CY, Strano MS, Nuckolls C, Blanchet G. J. Phys. Chem. C 2007; 111: 17947
  • 15 Ray DiasJ. THEOCHEM 1989; 54: 57
  • 16 Pangborn AB, Giardello MA, Grubbs RH, Rosen RK, Timmers FJ. Organometallics 1996; 15: 1518