A Facile Synthesis for One Novel N-Heteroacene 9, 11, 20, 22-Tetraaza-Tetrapyridopentacene and Its Mechanism Analysis

References

• Bendikov, M., F. Wudl, and D. F. Perepichka. “Tetrathiafulvalenes, Oligoacenenes, and Their Buckminsterfullerene Derivatives: the Brick and Mortar of Organic Electronics.” Chem. Rev. 104 (2004): 4891–946.
   PubMed Web of Science ®Google Scholar
• Li, J., and Q. Zhang. “Mono- and Oligocyclic Aromatic Ynes and Diynes as Building Blocks to Approach Larger Acenes, Heteroacenes, and Twistacenes.”Synlett 24 (2013): 686–96.
   Web of Science ®Google Scholar
• Anthony, J. E. “Functionalized Acenes and Heteroacenes for Organic Electronics.” Chem. Rev. 106 (2006): 5028–48.
   PubMed Web of Science ®Google Scholar
• Anthony, J. E. “The Larger Acenes: Versatile Organic Semiconductors.” AngewandteChemie Int. Ed. 47 (2008): 452–83.
   PubMed Web of Science ®Google Scholar
• Jiang, D., and S. Dai. “Electronic Ground State of Higher Acenes.”J.Phy.Chem. A 112 (2008): 332–5.
   PubMed Web of Science ®Google Scholar
• Bendikov, M., H. M. Duong, K. Starkey, K. N. Houk, E. A. Carter, and F. Wudl, “Oligoacenes:  Theoretical Prediction of Open-Shell Singlet Diradical Ground States.” J. Am. Chem. Soc. 126 (2004): 7416–7.
   PubMed Web of Science ®Google Scholar
• Chun, D., Y. Cheng, and F. Wudl. “The Most Stable and Fully Characterized Functionalized Heptacene.” AngewandteChemie Int. Ed. 47 (2008): 8380–5.
   PubMed Web of Science ®Google Scholar
• Li, G., Y. Wu, J. Gao, C. Wang, J. Li, H. Zhang, Y. Zhao, Y. Zhao, and Q. Zhang. “Synthesis and Physical Properties of Four Hexazapentacene Derivatives.”J. Am. Chem. Soc. 134 (2012): 20298–301.
   PubMed Web of Science ®Google Scholar
• Payne, M. M., S. R. Parkin, and J. E. Anthony. “Functionalized Higher Acenes:  Hexacene and Heptacene.”J. Am. Chem. Soc. 127 (2005): 8028–9.
   PubMed Web of Science ®Google Scholar
• Xiao, J., C. D. Malliakas, Y. Liu, F. Zhou, G. Li, H. Su, M. G. Kanatzidis, F. Wudl, and Q. Zhang. “Clean Reaction Strategy to Approach a Stable, Green Heptatwistacene Containing a Single Terminal Pyrene Unit.”Chem. Asian J. 4 (2012): 672–5.
   Google Scholar
• Watanable, M., Y. J. Chang, S. W. Liu, T. H. Chao, K. Goto, M. M. Islam, C. H. Yuan, Y. T. Tao, T. Shinmyozu, and T. J. Chow. “The Synthesis, Crystal Structure and Charge-transport Properties of Hexacene.”Nat. Chem. 4 (2012): 574–8.
   PubMed Web of Science ®Google Scholar
• Kaur, I., N. N. Stein, R. P. Kopreski, and G. P. Miller. “Exploiting Substituent Effects for the Synthesis of a Photooxidatively Resistant Heptacene Derivative.”J. Am. Chem. Soc. 131 (2009): 3424–5.
   PubMed Web of Science ®Google Scholar
• Kaur, I., M. Jazdzky, N. N. Stein, P. Prusevich, and G. P. Miller. “Design, Synthesis, and Characterization of a Persistent Nonacene Derivative.”J. Am. Chem. Soc. 132 (2010): 1261–3.
   PubMed Web of Science ®Google Scholar
• Xiao, J., H. M. Duong, Y. Liu, W. Shi, L. Ji, G. Li, S. Li, X. W. Liu, J. Ma, F. Wudl, and Q. Zhang. “Synthesis and Structure Characterization of a Stable Nonatwistacene.”AngewandteChemie Int. Ed. 51 (2012): 6094–8.
   PubMed Web of Science ®Google Scholar
• Purushothaman, B., M. Bruzek, S. R. Parkin, A. F. Miller, and J. E. Anthony. “Synthesis and Structural Characterization of Crystalline Nonacenes.”AngewandteChemie Int. Ed. 50 (2011): 7013–7.
   PubMed Web of Science ®Google Scholar
• Aleshin, A. N., J. Y. Lee, S. W. Chu, J. S. Kim, and Y. W. Park. “Mobility Studies of Field-effect Transistor Structures BasedonAnthracene Single Crystals.” Appl. Phys. Lett. 84 (2004): 5383–5.
   Web of Science ®Google Scholar
• De Boer, R. W. I., T. M. Klapwijk, and A. F. Morpurgo. “Field-effect Transistors on Tetracene Single Crystals.”Appl. Phys. Lett. 83 (2003): 4345–7.
   Web of Science ®Google Scholar
• Wang, C., J. Wang, P. Li, J. Gao, S. Y. Tan, W. Xiong, B. Hu, P. S. Lee, Y. Zhao, and Q. Zhang. “Synthesis, Characterization, and Non-Volatile Memory Device Application of an N-Substituted Heteroacene.”Chem. Asian J. 9 (2014): 779–83.
   PubMed Web of Science ®Google Scholar
• Gu, P. Y., F. Zhou, J. Gao, G. Li, C. Wang, Q. F. Xu, Q. Zhang, and J. M. Lu. “Synthesis, Characterization, and Nonvolatile Ternary Memory Behavior of a Larger Heteroacene with Nine Linearly Fused Rings and Two Different Heteroatoms.”J. Am. Chem. Soc. 135 (2013): 14086–9.
   PubMed Web of Science ®Google Scholar
• Li, G., K. Zheng, C. Wang, K.S. Leck, F. Hu, X. W. Sun, and Q. Zhang. “Synthesis and Nonvolatile Memory Behaviors of Dioxatetraazapentacene Derivatives.”ACS Appl. Mater. Inter. 5 (2013): 6458–62.
   PubMed Web of Science ®Google Scholar
• Xiao, J., S. Liu, Y. Liu, L. Ji, X. Liu, H. Zhang, X. Sun, and Q. Zhang. “Synthesis, Structure, and Physical Properties of 5, 7, 14, 16-Tetraphenyl-8: 9, 12: 13-Bisbenzo-Hexatwistacene.” Chem. Asian J. 7 (2012): 561–4.
   PubMed Web of Science ®Google Scholar
• Xiao, J., Y. Divayana, Q. Zhang, H. M. Doung, H. Zhang, F. Boey, X. W. Sun, and F. Wudl. “Synthesis, Structure, and Optoelectronic Properties of a New Twistacene 1, 2, 3, 4, 6, 13-Hexaphenyl-7:8, 11:12-Bisbenzo-Pentacene.”J. Mater. Chem. 20 (2010): 8167–70
   Web of Science ®Google Scholar
• Gorodetsky, A. A., M. Cox, N. J. Tremblay, I. Kymissis, and C. Nuckolls. “Solar Cells from a Solution ProcessablePentacene with Improved Air Stability.”Chem. Mater. 21 (2009): 4090–2.
   Web of Science ®Google Scholar
• Wang, C., H. Dong, W. Hu, Y. Liu, and D. Zhu. “Semiconducting π-Conjugated Systems in Field-Effect Transistors: A Material Odyssey of Organic Electronics.” Chem. Rev. 112 (2012): 2208–67.
   PubMed Web of Science ®Google Scholar
• Kim, F. S., G. Ren, and S. A. Jenekhe. “One-Dimensional Nanostructures of π-Conjugated Molecular Systems: Assembly, Properties, and Applications from Photovoltaics, Sensors, and Nanophotonics to Nanoelectronics.” Chem. Mater. 23 (2011): 682–732.
   Web of Science ®Google Scholar
• Allard, S., M. Forster, B. Souharce, H. Thiem, and U. Scherf. “Organic Semiconductors for Solution-Processable Field-Effect Transistors (OFETs).”AngewandteChemie Int. Ed. 47 (2008): 4070–98.
   PubMed Web of Science ®Google Scholar
• Qiu, L., C. Yu, N. Zhao, W. Chen, Y. Guo, X. Wan, R. Yang, and Y. Liu. “An Expedient Synthesis of Fused Heteroacenes Bearing a Pyrrolo[3, 2-b]Pyrrole Core.” Chem. Commun. 48 (2012):12225–7.
   PubMed Web of Science ®Google Scholar
• Winkler, M., and K. N. Houk. “Nitrogen-Rich Oligoacenes:  Candidates for n-Channel Organic Semiconductors.” J. Am. Chem. Soc. 129 (2007): 1805–15.
   PubMed Web of Science ®Google Scholar
• Bunz, U. H. F. “The Larger N-heteroacenes.” Pure Appl. Chem. 82 (2010): 953–68.
   Web of Science ®Google Scholar
• Aurelio, M. A., K. Niksa, V. Giovanni, M. Massimo, P. Francesco, and P. Maurizio. “Facile Synthesis of Highly Stable Tetraazaheptacene and Tetraazaoctacene Dyes.” Chem. Asian J. 5 (2010): 482–5.
   PubMed Web of Science ®Google Scholar
• Muriel, R., K. Michael, V. Emilie, C. S. P. Tamara, B. Cornelia, and E. W. Vance. “Photochromic Benzo[g]quinoxalines.”Canadian J. Chem. 89 (2011): 297–302.
   Web of Science ®Google Scholar
• Hemant, V. C., K. A. Laxman, and P. B. Babasaheb. “Polyethylene Glycol in Water: A Simple, Efficient and Green Protocol for the Synthesis of Quinoxalines.” J. Chem. Sci. 123 (2011): 477–83.
   Web of Science ®Google Scholar
• Zhang, X. Z., J. X. Wang, Y. J. Sun, and H. W. Zhan. “Synthesis of Quinoxaline Derivatives Catalyzed by PEG-400.”Chinese Chem. Lett. 21 (2010): 395–8.
   Google Scholar
• Leandro, A. E., and C. N. Douglas. “Synthesis and Photophysics of Dibenz[a,c]phenazine Derivatives.” Organic Lett. 13 (2011): 3304–7.
   PubMedGoogle Scholar
• Zhao, Z., D. W. David, E. W. Scott, H. L. William, Y. Wang, and W. L. Craig. “General Microwave-assisted Protocols for the Expedient Synthesis of Quinoxalines and Heterocyclic Pyrazines.” Tetrahedron Lett. 45 (2004): 4873–6.
   Web of Science ®Google Scholar
• Li, G., J. Miao, J. Gao, J. Cao, J. Zhu, B. Liu, and Q. Zhang. “Preparation and Photoelectrochemical Behavior of 1, 4, 6, 8, 11, 13-Hexazapentacene (HAP).” Chem. Commun. 50 (2014): 7656–8.
   PubMed Web of Science ®Google Scholar
• Zhao, J., G. Li, C. Wang, W. Chen, S. C. J. Loo, and Q. Zhang. “A New N-substituted Heteroacene Can Detect CN− and F− Anions via Anion–π Interaction.” RSC Adv. 3 (2013): 9653–7.
   Web of Science ®Google Scholar
• Li, G., G. Long, W. Chen, F. Hu, Y. Chen, and Q. Zhang. “A Concise Method for Synthesizing 1, 4, 8, 11-Tetraaza-6, 13-dioxapentacene Derivatives.” Asian J. Organic Chem. 2 (2013): 852–6.
   Web of Science ®Google Scholar
• Wang, C., T. Okabe, G. Long, D. Kuzuhara, Y. Zhao, N. Aratani, H. Yamada, and Q. Zhang. “A Novel D–π–A Small Molecule with N-heteroacene as Acceptor Moiety for Photovoltaic Application.”Dyes and Pigments 122 (2015): 231–7.
   Web of Science ®Google Scholar