Synthesis of Large Pyrene-Fused Azaacenes

Abstract

The facile synthesis of pyrene-fused tetraazaheptacene and tetraazaoctacene is reported. The new compounds are fully soluble in common organic solvents. The absorption spectra of both compounds reveal that they have low energy gaps. The structure of tetraazaoctacene was confirmed by single crystal X-ray diffraction analysis.

Key words

azaacenes - crystal structures - electronic materials - pyrene - solubility

• References

• 1 Anthony JE. Angew. Chem. Int. Ed. 2008; 47: 452
• 2 Cheng YC, Silbey RJ, da Silva Filho DA, Calbert JP, Cornil J, Bredas JL. J. Chem. Phys. 2003; 118: 3764
• 3 Clar E. Polycyclic Hydrocarbons . Vol. 1. Academic Press; New York: 1964
• 4a Purushothaman B, Parkin SR, Anthony JE. Org. Lett. 2010; 12: 2060
• 4b Payne MM, Parkin SR, Anthony JE. J. Am. Chem. Soc. 2005; 127: 8028
• 4c Chun D, Cheng Y, Wudl F. Angew. Chem. Int. Ed. 2008; 47: 8380
• 4d Qu H, Chi C. Org. Lett. 2010; 12: 3360
• 4e Kaur I, Stein NN, Kopreski RP, Miller GP. J. Am. Chem. Soc. 2009; 131: 3424
• 4f Kaur I, Jazdzyk M, Stein NN, Prusevich P, Miller GP. J. Am. Chem. Soc. 2010; 132: 1261
• 5 Miao Q, Nguyen T.-Q, Someya T, Blanchet GB, Nuckolls C. J. Am. Chem. Soc. 2003; 125: 10284
• 6a Miao S, Appleton AL, Berger N, Barlow S, Marder SR, Hardcastle KI, Bunz UH. F. Chem. Eur. J. 2009; 15: 4990
• 6b Appleton AL, Brombosz SM, Bralow S, Sears JS, Bredas J.-L, Marder SR, Bunz UH. F. Nat. Commun. 2010; 1: 90
• 6c Tverskoy O, Rominger F, Peters A, Himmel H.-J, Bunz UH. F. Angew. Chem. Int. Ed. 2011; 50: 3557
• 6d Lindner BD, Engelhart JU, Tverskoy O, Appleton AL, Rominger F, Peters A, Himmel H.-J, Bunz UH. F. Angew. Chem. Int. Ed. 2011; 50: 8588
• 6e Engelhart JU, Lindner BD, Tverskoy O, Rominger F, Bunz UH. F. Chem. Eur. J. 2013; 19: 15089
• 6f Appleton AL, Barlow S, Marder SR, Hardcastle KI, Bunz UH. F. Synlett 2011; 1983
• 7 Winkler M, Houk KN. J. Am. Chem. Soc. 2007; 129: 1805
• 8a Liang Z, Tang Q, Mao R, Liu D, Xu J, Miao Q. Adv. Mater. 2011; 23: 5514
• 8b Liang Z, Tang Q, Xu J, Miao Q. Adv. Mater. 2011; 23: 1535
• 9 Figueira-Duarte TM, Müllen K. Chem. Rev. 2011; 111: 7260
• 10 Wu Y, Yin Z, Xiao J, Liu Y, Wei F, Tan KJ, Kloc C, Huang L, Yan Q, Hu F, Zhang H, Zhang Q. ACS Appl. Mater. Interfaces 2012; 4: 1883
• 11 Hu J, Zhang D, Harris FW. J. Org. Chem. 2005; 70: 707
• 12a Mateo-Alonso A, Kulisic N, Valentic G, Marcaccio M, Paolucci F, Prato M. Chem. Asian J. 2010; 5: 482
• 12b Kulisic N, More S, Mateo-Alonso A. Chem. Commun. 2011; 47: 514
• 12c More S, Bhosale R, Choudhary S, Mateo-Alonso A. Org. Lett. 2012; 14: 4170
• 12d More S, Bhosale R, Mateo-Alonso A. Chem. Eur. J. 2014; 20: 10626
• 12e Chen S, Raad FS, Ahmida M, Kaafarani BR, Eichhorn SH. Org. Lett. 2013; 15: 558
• 12f Gao B, Wang M, Cheng Y, Wang L, Jing X, Wang F. J. Am. Chem. Soc. 2008; 130: 8297
• 13 Wang C, Dong H, Hu W, Liu Y, Zhu D. Chem. Rev. 2012; 112: 2208
• 14 Miao S, Brombosz SM, Schleyer Pv. R, Wu JI, Barlow S, Marder SR, Hardcastle KI, Bunz UH. F. J. Am. Chem. Soc. 2008; 130: 7339
• 15 The structures of compounds 3 and 6 were confirmed by single crystal X-ray analysis. CCDC 1025759 (3) and CCDC 1025758 (6) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge­ Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data_request/cif or or by writing to the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: [phone]; E-mail: [e-mail].
• 16 More S, Choudhary S, Higelin A, Krossing I, Melle-Franco M, Mateo-Alonso A. Chem. Commun. 2014; 50: 1976
• 17 Lindner BD, Zhang Y, Höfle S, Berger N, Teusch C, Jesper M, Hardcastle KI, Qian X, Lemmer U, Colsmann A, Bunz UH. F, Hamburger M. J. Mater. Chem. C 2013; 1: 5718
• 18 Bunz UH. F, Engelhart JU, Lindner BD, Schaffroth M. Angew. Chem. Int. Ed. 2013; 52: 3810