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

Bassam Alameddine; Sofia Martin Caba; Mauro Schindler; Titus A. Jenny

doi:10.1055/s-0031-1291010

Synthesis, Table of Contents

Synthesis 2012; 44(12): 1928-1934
DOI: 10.1055/s-0031-1291010

paper

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

Bassam Alameddine

^aDepartment of Mathematics and Natural Sciences, Gulf University for Science and Technology, Hawally 32093, Kuwait

,

Sofia Martin Caba

^bChemistry Department, University of Fribourg, chemin du Musée 9, 1700 Fribourg, Switzerland, Fax: +41(26)3009739 Email: titus.jenny@unifr.ch

,

Mauro Schindler

^bChemistry Department, University of Fribourg, chemin du Musée 9, 1700 Fribourg, Switzerland, Fax: +41(26)3009739 Email: titus.jenny@unifr.ch

,

Titus A. Jenny*

^bChemistry Department, University of Fribourg, chemin du Musée 9, 1700 Fribourg, Switzerland, Fax: +41(26)3009739 Email: titus.jenny@unifr.ch

› Author Affiliations

Abstract

All articles of this category

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.

Key words

fused-ring systems - cross-coupling - Diels–Alder reaction - cyclodehydrogenation - polycycles

Full Text

References

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

7a Doetz F, Brand JD, Ito S, Gherghel L, Müllen K. J. Am. Chem. Soc. 2000; 122: 7707
7b O’Brien M, Denton R, Ley SV. Synthesis 2011; 1157
7c Ullah I, Nawaz M, Villinger A, Langer P. Synlett 2011; 1895

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