Quinoxalinophenanthrophenazine Compounds in Organic Optoelectronic Applications Bilal Kaafarani1; 1AMERICAN UNIVERSITY OF BEIRUT, Beirut, Lebanon; PAPER: 203/AdvancedMaterials/Regular (Oral) SCHEDULED: 14:50/Sat. 26 Oct. 2019/Leda (99/Mezz. F) ABSTRACT: Fused, ladder-type organic materials have inherent advantages, such as extended Pi-frameworks, favorable stacking behavior in the solid state, conductivity, and high field-effect mobility. We have reported a wide range of quinoxalinophenanthrophenazine (TQPP) compounds. The introduction of nitrogen atoms in the TQPP core decreases the HOMO-LUMO gap, making the compounds of more interest in electronic applications. Besides, the planarity of the core in the TQPP compounds facilitates the efficient cofacial stacking of the materials in the solid state and increases the intermolecular Pi-orbital overlap. Combining the electronic properties of the electron-deficient TQPP chromophore with the predisposition of the TQPP compounds to self-organize into efficient self-assembled Pi-Pi columnar stacks in a single molecule offers an interesting combination of physical properties and, perhaps, a route to new materials for electronic applications. In this talk, we will discuss the different properties and features of the TQPP compounds. References: 1. Kaafarani, B. R.; El-Assaad, T. H.; Smith, W. A.; Ryno, S. M.; Hermerschmidt, F.; Lyons, J.; Patra, D.; Wex, B.; List-Kratochvil, E. J. W.; Risko, C.; Barlow, S.; Marder, S. R. “Bis(tercarbazole) pyrene and tetrahydropyrene derivatives: photophysical and electrochemical properties, theoretical modeling, and OLEDs”, J. Mater. Chem. C 2019, 7, 5009 - 5018. 2. Taing, H.; Cassar, A. M.; Ocheje, M. U.; Rondeau-Gagne, S.; El-Assaad, T. H.; Sharabati, C. A.; Kaafarani, B. R.; Eichhorn, S. H. “Self-assembly of Board-shaped Diketopyrrolopyrrole and Isoindigo Mesogens Into Columnar Pi-Pi Stacks”, ChemPlusChem 2019, 84, 103-106. 3. Fratczak, E. Z.; Makowski, T.; Moustafa, R. M.; El-Assaad, T. H.; Moneta, M. E.; Uznanski, P.; Kaafarani, B. R. “Spectroscopic Characterization of Structural Properties of Quinoxalinophenanthrophenazines Thin Films”, J. Mater. Chem. C 2018, 6, 781-789. 4. Wex, B.; Kaafarani, B. R. “Perspective on Carbazole-Based Organic Compounds as Emitters and Hosts in TADF Applications”, J. Mater. Chem. C 2017, 5, 8622-8653. 5. Altarawneh, S.; Nahar, S.; Arachchige, I. U.; El-Ballouli, A. O.; Hallal, K. M.; Kaafarani, B. R.; Rabbani, M. G.; El-Kaderi, H. M. “Highly Porous and Photoluminescent QuinoxalinoPhenanthroPhenazine-Derived Benzimidazole-Linked Polymers”, J. Mater. Chem. A 2015, 3, 3006-3010. 6. El-Ballouli, A. O.; Kayal, H.; Shuai, C.; Zeidan, T. A.; Raad, F. S.; Leng, S.; Wex, B.; Cheng, S. Z. D.; Eichhorn, S. H.; Kaafarani, B. R. “Lateral Extension Induces Columnar Mesomorphism in Crucifix Shaped Quinoxalinophenanthrophenazines”, Tetrahedron 2015, 71, 308-314. 7. Makowski, T.; Moustafa, R. M.; Uznanski, P.; Zajaczkowski, W.; Pisula, W.; Tracz, A.; Kaafarani, B. R. “Structural, Thermo-Optical, and Photophysical Properties of Highly Oriented Thin Films of Quinoxalinophenanthrophenazine Derivative”, J. Phys. Chem. C 2014, 118, 18736-18745. 8. Chen, S.; Raad, F. S.; Ahmida, M.; Kaafarani, B. R.; Eichhorn, H. S. “Columnar Mesomorphism of Fluorescent Board-Shaped Quinoxalinophenanthrophenazine Derivatives With Donor-Acceptor Structure”, Org. Lett. 2013, 15, 558-561. 9. Kaafarani, B. R. “Discotic Liquid Crystals for Opto-Electronic Applications”, Chem. Mater. 2011, 23, 378-396. |