Structural and Optical Properties of New Naphthalene and Perylene Imide Imidazoles

References

• Herrmann, A., and K. Mullen. “From Industrial Colorants to Single Photon Sources and Biolabels: The Fascination and Function of Rylene Dyes.” Chem. Lett. 35 (2006): 978–85.
   Web of Science ®Google Scholar
• Li, C., and H. Wonneberger. “Perylene Imides for Organic Photovoltaics: Yesterday, Today, and Tomorrow.” Adv. Mater. 24 (2012): 613–36.
   PubMed Web of Science ®Google Scholar
• Zhan, X., A. Facchetti, S. Barlow, T. J. Marks, M. A. Ratner, M. R. Wasielewski, and S. R. Marder. “Rylene and Related Diimides for Organic Electronics.” Adv. Mater. 23 (2011): 268–84.
   PubMed Web of Science ®Google Scholar
• Jung, C., N. Ruthardt, R. Lewis, J. Michaelis, B. Sodeik, F. Nolde, K. Peneva, K. Mullen, and C. Brauchle. “Photophysics of New Water-Soluble Terrylenediimide Derivatives and Applications in Biology.” Chem. Phys. Chem. 10 (2009): 180–90.
   Web of Science ®Google Scholar
• Peneva, K., G. Mihov, F. Nolde, S. Rocha, J. Hotta, K. Braeckmans, J. Hofkens, H. Uji-i, A. Herrmann, and K. Mullen. “Water-Soluble Monofunctional Perylene and Terrylene Dyes: Powerful Labels for Single-Enzyme Tracking.” Angew. Chem. Int. Ed. 47 (2008): 3372–5.
   PubMed Web of Science ®Google Scholar
• Zang, L., Y. Che, and J. S. Moore. “One-Dimensional Self-Assembly of Planar π-Conjugated Molecules: Adaptable Building Blocks for Organic Nanodevices.” Acc. Chem. Res. 41 (2008): 1596–608.
   PubMed Web of Science ®Google Scholar
• Chen, Z., A. Lohr, C. R. Saha-Möller, and F. Wurthner. “Self-Assembled π-stacks of Functional Dyes in Solution: Structural and Thermodynamic Features.” Chem. Soc. Rev. 38 (2009): 564–84.
   PubMed Web of Science ®Google Scholar
• Calzado, E. M., J. M. Villalvilla, P. G. Boj, J. A. Quintana, R. Gomez, J. L. Segura, and M. A. Diaz-Garcia. “Amplified Spontaneous Emission in Polymer Films Doped with a Perylenediimide Derivative.” J. Phys. Chem. C 111 (2007): 13595–605.
   Web of Science ®Google Scholar
• Jones, B. A., A. Facchetti, T. J. Marks, and M. R. Wasielewski. “Cyanonaphthalene Diimide Semiconductors for Air-Stable, Flexible, and Optically Transparent n-Channel Field-Effect Transistors.” Chem. Mater. 19 (2007): 2703–5.
   Web of Science ®Google Scholar
• Gregg, B. A., and R. A. Cormier. “Doping Molecular Semiconductors:  n-Type Doping of a Liquid Crystal Perylene Diimide.” J. Am. Chem. Soc. 123 (2001): 7959–60.
   PubMed Web of Science ®Google Scholar
• Wen, Y., Y. Liu, C. Di, Y. Wang, X. Sun, Y. Guo, J. Zheng, W. Wu, S. Ye, and G. Yu. “Improvements in Stability and Performance of N, N′‐Dialkyl Perylene Diimide‐Based n‐Type Thin‐Film Transistors” Adv. Mater. 21 (2009): 1631–5.
   Web of Science ®Google Scholar
• Gao, X., C. Di, Y. Hu, X. Yang, H. Fan, F. Zhang, Y. Liu, H. Li, and D. Zhu. “Core-Expanded Naphthalene Diimides Fused with 2-(1,3-Dithiol-2-Ylidene)Malonitrile Groups for High-Performance, Ambient-Stable, Solution-Processed n-Channel Organic Thin Film Transistors.” J. Am. Chem. Soc. 132 (2010): 3697–9.
   PubMed Web of Science ®Google Scholar
• Ortiz, R. P., H. Herrera, R. Blanco, H. Huang, A. Facchetti, T. J. Marks, Y. Zheng, and J. L. Sagura. “ Organic n-Channel Field-Effect Transistors Based on Arylenediimide-Thiophene Derivatives.” J. Am. Chem. Soc. 132 (2010): 8440–52.
   PubMed Web of Science ®Google Scholar
• Ortiz, R. P., H. Herrera, C. Seoane, J. L. Segura, A. Facchetti, and T. J. Marks. “Rational Design of Ambipolar Organic Semiconductors: Is Core Planarity Central to Ambipolarity in Thiophene-Naphthalene Semiconductors.” Chem. Eur. J. 18 (2012): 532–43.
   PubMed Web of Science ®Google Scholar
• Deng, P., Y. Yan, S. D. Wang, and Q. Zhang. “Naphthoylene (trifluoromethyl benzimidazole)-Dicarboxylic Acid Imides for High-Performance n-Type Organic Field-Effect Transistors.” Chem. Commun. 48 (2012): 2591–3.
   PubMed Web of Science ®Google Scholar
• Shao, J., J. Chang, and C. Chi. “Solution-Processable n-Type Semiconductors Based on Unsymmetrical Naphthalene Imides: Synthesis, Characterization, and Applications in Field-Effect Transistors.” Asian. J. Chem. 9 (2014): 253–60.
   Google Scholar
• Zhao, J., G. Li, C. Wang, W. Chen, S. Chye, J Loo, and Q Zhang. “A new N-Substituted Heteroacene Can Detect CN2 and F2 Anions via Anion–p Interaction.” RSC Adv. 3 (2013): 9653–7.
   Web of Science ®Google Scholar
• Fery-Forgues, S., and D. Lavabre. “Are Fluorescence Quantum Yields So Tricky to Measure? A Demonstration Using Familiar Stationery Products.” J. Chem Educ. 76 (1999): 1260–4.
   Web of Science ®Google Scholar
• Bruker, SADABS, (Madison, Wisconsin: USA: Bruker AXS Inc., 2005).
   Google Scholar
• Bruker, APEX2 (Version 2011.4-1), (Madison, Wisconsin: USA: Bruker AXS Inc., 2008).
   Google Scholar
• Sheldrick, G M SHELXS 97. Programs for crystal structure solution.
   Google Scholar
• Spek, A. L. “Single-Crystal Structure Validation with the Program PLATON.” J. Appl. Cryst. 36 (2003): 7–13.
   Web of Science ®Google Scholar
• Macrae, C. F., P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler, and J. van de Streek. “Mercury: Visualization and Analysis of Crystal Structures.” J. Appl. Cryst. 39 (2006): 453–7.
   Web of Science ®Google Scholar
• Pennington, W. T. “DIAMOND- Visual Crystal Structure Information System.” J. Appl. Cryst. 32 (1999): 1028–29.
   Web of Science ®Google Scholar
• Burmester, C., and R. Faust. “A Reliable Route to 1,2-Diamino-4,5-Phthalodinitrile.” Synthesis 8 (2008): 1179–82.
   Google Scholar
• Hu, G., L. Lv, L. Li, Q. Zhang, X. Li, Y. Tian, J. Wu, B. Jin, H. Zhou, J. Yang, and S Zhang. “Design, Synthesis, Photoluminescence and Electrochemiluminescence Properties of Naphthalimide Derivative and its Silver Complex.” Dyes Pigments 89 (2011): 105–10.
   Web of Science ®Google Scholar
• Wicklein, A., M. Muth, and M. Thelakkat. “Swallow-Tail Substituted Liquid Crystalline Perylene Bisimides: Synthesis and Thermotropic Properties.” J. Am. Chem. Soc. 131 (2009): 14442–53.
   PubMed Web of Science ®Google Scholar
• Mamada, M., C. Perez-Bolivar, and P. Anzenbacher. “Green Synthesis of Polycyclic Benzimidazole Derivatives and Organic Semiconductors.” Org. Lett. 13 (2011): 4882–5.
   PubMed Web of Science ®Google Scholar
• Kumru, U., F. Dumoulin, E. Jeanneau, F. Yuksel, Y. Cabezas, Y. Zorlu, and V. Ahsen. “4,5-, 3,6-, and 3,4,5,6-tert-Butylsulfanylphthalonitriles: Synthesis and Comparative structural and Spectroscopic Analyses.” Struct. Chem. 23 (2012): 175–83.
   Web of Science ®Google Scholar
• Krüger, H., S. Janietz, D. Sainova, D. Dobreva, N. Koch, and A. Vollmer. “Hybrid Supramolecular Naphthalene Diimide-thiophene Structures and their Application in Polymer Electronics” Adv. Funct. Mater. 17 (2007): 3715–23.
   Web of Science ®Google Scholar
• Gaussian 09, Revision D.01, Frisch, M J, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox. (Wallingford CT: Gaussian Inc., 2009).
   Google Scholar
• O'Boyle, N. M., A. L. Tenderholt, and K. M. Langner. “cclib: A library for Package-Independent Computational Chemistry Algorithms.” J. Comp. Chem. 29 (2008): 839–45.
   PubMed Web of Science ®Google Scholar
• Fortage, J., M. Séverac, C. Houarner-Rassin, Y. Pellegrin, E. Blart, and F. Odobel. “Synthesis of New Perylene Imide Dyes and Their Photovoltaic Performances in Nanocrystalline TiO2 Dye-Sensitized Solar Cells.” J. Photochem. Photobiol. A. Chem. 197 (2008): 156–69.
   Web of Science ®Google Scholar
• Oh, S. H., B. G. Kim, S. J. Yun, M. Maheswaraa, K. Kim, and J. Y. Do. “The Synthesis of Symmetric and Asymmetric Perylene Derivatives and Their Optical Properties.” Dyes Pigments 85 (2010): 37–42.
   Web of Science ®Google Scholar
• Wicklein, A., P. Kohn, L. Ghazaryan, T. Thurn-Albrecht, and M. Thelakkat. “Synthesis and Structure Elucidation of Discotic Liquid Crystalline Perylene Imide Benzimidazole.” Chem. Commun. 46 (2010): 2328–30.
   PubMed Web of Science ®Google Scholar
• Rätsep, M., J. Linnanto, and A. Freiberg. “Mirror Symmetry and Vibrational Structure in Optical Spectra of Chlorophyll a.” J. Chem. Phys. 130 (2009): 194501.
   PubMed Web of Science ®Google Scholar
• Reichardt, C., and T. Welton. Solvents and Solvent Effects in Organic Chemistry. (Weinheim: Wiley-VCH Verlag, 2011, 1979).
   Google Scholar