Extended Ladder-Type Benzo[k]tetraphene-Derived Oligomers
Jongbok Lee
Department of Chemistry, Texas A&M University, 3255 TAMU, College Station, TX, 77843-3255 USA
Search for more papers by this authorHuanbin Li
MOE Key Laboratory of Macromolecular Synthesis and Functionalization, State Key Laboratory of Silicon Materials, Department of Polymer Science and Engineering, Zhejiang University, 38 Zheda Rd, Hangzhou, 310027 China
Search for more papers by this authorAlexander J. Kalin
Department of Chemistry, Texas A&M University, 3255 TAMU, College Station, TX, 77843-3255 USA
Search for more papers by this authorTianyu Yuan
Department of Materials Science and Engineering, Texas A&M University, 3003 TAMU, College Station, TX, 77843-3003 USA
Search for more papers by this authorChenxu Wang
Department of Materials Science and Engineering, Texas A&M University, 3003 TAMU, College Station, TX, 77843-3003 USA
Search for more papers by this authorTroy Olson
Department of Chemistry, Texas A&M University, 3255 TAMU, College Station, TX, 77843-3255 USA
Search for more papers by this authorHanying Li
MOE Key Laboratory of Macromolecular Synthesis and Functionalization, State Key Laboratory of Silicon Materials, Department of Polymer Science and Engineering, Zhejiang University, 38 Zheda Rd, Hangzhou, 310027 China
Search for more papers by this authorCorresponding Author
Lei Fang
Department of Chemistry, Texas A&M University, 3255 TAMU, College Station, TX, 77843-3255 USA
Department of Materials Science and Engineering, Texas A&M University, 3003 TAMU, College Station, TX, 77843-3003 USA
Search for more papers by this authorJongbok Lee
Department of Chemistry, Texas A&M University, 3255 TAMU, College Station, TX, 77843-3255 USA
Search for more papers by this authorHuanbin Li
MOE Key Laboratory of Macromolecular Synthesis and Functionalization, State Key Laboratory of Silicon Materials, Department of Polymer Science and Engineering, Zhejiang University, 38 Zheda Rd, Hangzhou, 310027 China
Search for more papers by this authorAlexander J. Kalin
Department of Chemistry, Texas A&M University, 3255 TAMU, College Station, TX, 77843-3255 USA
Search for more papers by this authorTianyu Yuan
Department of Materials Science and Engineering, Texas A&M University, 3003 TAMU, College Station, TX, 77843-3003 USA
Search for more papers by this authorChenxu Wang
Department of Materials Science and Engineering, Texas A&M University, 3003 TAMU, College Station, TX, 77843-3003 USA
Search for more papers by this authorTroy Olson
Department of Chemistry, Texas A&M University, 3255 TAMU, College Station, TX, 77843-3255 USA
Search for more papers by this authorHanying Li
MOE Key Laboratory of Macromolecular Synthesis and Functionalization, State Key Laboratory of Silicon Materials, Department of Polymer Science and Engineering, Zhejiang University, 38 Zheda Rd, Hangzhou, 310027 China
Search for more papers by this authorCorresponding Author
Lei Fang
Department of Chemistry, Texas A&M University, 3255 TAMU, College Station, TX, 77843-3255 USA
Department of Materials Science and Engineering, Texas A&M University, 3003 TAMU, College Station, TX, 77843-3003 USA
Search for more papers by this authorGraphical Abstract
Aromatic “rungs” of the ladder: A highly efficient thermodynamic annulation enables the bottom-up syntheses of well-defined, fused-ring oligomers that imitate graphene nanostripes. Electronic structures and crystallization dynamics of these oligomers are highly dependent on the molecular size.
Abstract
Well-defined, fused-ring aromatic oligomers represent promising candidates for the fundamental understanding and application of advanced carbon-rich materials, though bottom-up synthesis and structure–property correlation of these compounds remain challenging. In this work, an efficient synthetic route was employed to construct extended benzo[k]tetraphene-derived oligomers with up to 13 fused rings. The molecular and electronic structures of these compounds were clearly elucidated. Precise correlation of molecular sizes and crystallization dynamics was established, thus demonstrating the pivotal balance between intermolecular interaction and molecular mobility for optimized processing of highly ordered solids of these extended conjugated molecules.
Supporting Information
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References
- 1
- 1aH. Klauk, M. Halik, U. Zschieschang, G. Schmid, W. Radlik, W. Weber, J. Appl. Phys. 2002, 92, 5259–5263;
- 1bY. Geerts, G. Klärner, K. Müllen in Electronic Materials: The Oligomer Approach, Wiley-VCH, Weinheim, 2007, pp. 48–52;
- 1cJ. E. Anthony, Angew. Chem. Int. Ed. 2008, 47, 452–483; Angew. Chem. 2008, 120, 460–492;
- 1dG. Xue, C. Fan, J. Wu, S. Liu, Y. Liu, H. Chen, H. L. Xin, H. Li, Mater. Horiz. 2015, 2, 344–349.
- 2
- 2aF. B. Mallory, K. E. Butler, A. C. Evans, E. J. Brondyke, C. W. Mallory, C. Yang, A. Ellenstein, J. Am. Chem. Soc. 1997, 119, 2119–2124;
- 2bH. Okamoto, N. Kawasaki, Y. Kaji, Y. Kubozono, A. Fujiwara, M. Yamaji, J. Am. Chem. Soc. 2008, 130, 10470–10471;
- 2cY. Kaji, N. Kawasaki, X. Lee, H. Okamoto, Y. Sugawara, S. Oikawa, A. Ito, H. Okazaki, T. Yokoya, A. Fujiwara, Y. Kubozono, Appl. Phys. Lett. 2009, 95, 183302;
- 2dF. B. Mallory, C. W. Mallory, C. K. Regan, R. J. Aspden, A. B. Ricks, J. M. Racowski, A. I. Nash, A. V. Gibbons, P. J. Carroll, J. M. Bohen, J. Org. Chem. 2013, 78, 2040–2045.
- 3M. Saito, Y. Nakano, H. Nakamura, H. Kondo, U.S Patent US20110220884 A1, 2011.
- 4U. Rui, M. Satoshi, N. Yutaka, Chem. Lett. 2012, 41, 215–217.
- 5
- 5aT.-A. Chen, T.-J. Lee, M.-Y. Lin, S. M. A. Sohel, E. W.-G. Diau, S.-F. Lush, R.-S. Liu, Chem. Eur. J. 2010, 16, 1826–1833;
- 5bB. T. Haire, K. W. J. Heard, M. S. Little, A. V. S. Parry, J. Raftery, P. Quayle, S. G. Yeates, Chem. Eur. J. 2015, 21, 9970–9974.
- 6K. Kentaroh, K. Takuya, N. Masashi, I. Yutaka, A. Yoshio, K. Fumitoshi, Chem. Lett. 2011, 40, 300–302.
- 7G. Povie, Y. Segawa, T. Nishihara, Y. Miyauchi, K. Itami, Science 2017, 356, 172–175.
- 8
- 8aM. B. Goldfinger, T. M. Swager, J. Am. Chem. Soc. 1994, 116, 7895–7896;
- 8bK. Chmil, U. Scherf, Acta Polym. 1997, 48, 208–211.
- 9
- 9aC. Wetzel, E. Brier, A. Vogt, A. Mishra, E. Mena-Osteritz, P. Bäuerle, Angew. Chem. Int. Ed. 2015, 54, 12334–12338; Angew. Chem. 2015, 127, 12511–12515;
- 9bL. Guo, K. F. Li, X. Zhang, K. W. Cheah, M. S. Wong, Angew. Chem. Int. Ed. 2016, 55, 10639–10644; Angew. Chem. 2016, 128, 10797–10802;
- 9cW. Yang, J. H. S. K. Monteiro, A. de Bettencourt-Dias, V. J. Catalano, W. A. Chalifoux, Angew. Chem. Int. Ed. 2016, 55, 10427–10430; Angew. Chem. 2016, 128, 10583–10586;
- 9dT. Zheng, Z. Cai, R. Ho-Wu, S. H. Yau, V. Shaparov, T. Goodson, L. Yu, J. Am. Chem. Soc. 2016, 138, 868–875;
- 9eY. Wang, H. Guo, S. Ling, I. Arrechea-Marcos, Y. Wang, J. T. Lopez Navarrete, R. P. Ortiz, X. Guo, Angew. Chem. Int. Ed. 2017, 56, 9924–9929; Angew. Chem. 2017, 129, 10056–10061.
- 10
- 10aM. C. Bonifacio, C. R. Robertson, J.-Y. Jung, B. T. King, J. Org. Chem. 2005, 70, 8522–8526;
- 10bJ. Lee, B. B. Rajeeva, T. Yuan, Z.-H. Guo, Y.-H. Lin, M. Al-Hashimi, Y. Zheng, L. Fang, Chem. Sci. 2016, 7, 881–889.
- 11Oligomers with even number of fused rings are not feasible using this strategy because of the unsymmetric nature of the precursors.
- 12C. Zhu, A. U. Mu, Y.-H. Lin, Z.-H. Guo, T. Yuan, S. E. Wheeler, L. Fang, Org. Lett. 2016, 18, 6332–6335.
- 13
- 13aR. Rieger, K. Müllen, J. Phys. Org. Chem. 2010, 23, 315–325;
- 13bE. Clar in Polycyclic Hydrocarbons, Vol. 1, Springer Berlin Heidelberg, Berlin, 1964, pp. 40–69.
10.1007/978-3-662-01665-7_7 Google Scholar
- 14H. Meier, U. Stalmach, H. Kolshorn, Acta Polym. 1997, 48, 379–384.
- 15J. Grimme, M. Kreyenschmidt, F. Uckert, K. Müllen, U. Scherf, Adv. Mater. 1995, 7, 292–295.
- 16F. C. Grozema, P. T. van Duijnen, Y. A. Berlin, M. A. Ratner, L. D. A. Siebbeles, J. Phys. Chem. B 2002, 106, 7791–7795.
- 17L. Chen, Y. Hernandez, X. Feng, K. Müllen, Angew. Chem. Int. Ed. 2012, 51, 7640–7654; Angew. Chem. 2012, 124, 7758–7773.
- 18C. K. Ober, S. Z. D. Cheng, P. T. Hammond, M. Muthukumar, E. Reichmanis, K. L. Wooley, T. P. Lodge, Macromolecules 2009, 42, 465–471.
- 19S. Krotzky, C. Morchutt, V. S. Vyas, B. V. Lotsch, R. Gutzler, K. Kern, J. Phys. Chem. C 2016, 120, 4403–4409.
- 20C. Zhou, Q. Cui, C. McDowell, M. Seifrid, X. Chen, J.-L. Brédas, M. Wang, F. Huang, G. C. Bazan, Angew. Chem. Int. Ed. 2017, 56, 9318–9321; Angew. Chem. 2017, 129, 9446–9449.
- 21D. Dini, M. J. F. Calvete, M. Hanack, Chem. Rev. 2016, 116, 13043–13233.
