LINEAR ACENES LINKED THIOPHENE, ELECTRONIC AND CHEMICAL PROPERTIES: PROSPECTS FOR MOLECULAR ORGANIC ELECTRONIC MATERIAL
DOI:
https://doi.org/10.11113/jt.v78.9199Keywords:
Ground state energy, coulomb potential, nuclear repulsion energy, Band gap energiesAbstract
We report a theoretical study of linear acene (n=1 to 7) linked thiophene properties functionality. The total ground state and band gap energies, Coulomb potential and nuclear repulsion energy are calculated by DFT, MP2 at B3LYP exchange level of the theory and 6-311G* basis set. The results are in good agreement with the experimental and theoretical values. It is found that the total ground state energy of the system and band gap energy decreases with an increasing number of electrons in the rings. The addition of thiophene molecules tends to improve the electronic and chemical properties of the linear acenes, the material exhibit potential application in the organic molecular electronic material.
References
Nicolas, Y., F. Castet, M. Devynck, P. Tardy, L. Hirsch, C. Labrugere, H. Allouchi, And T. Toupance. 2012. TIPS-Triphenodioxazine Versus TIPS-Pentacene: Enhanced Electron Mobility For N-Type Organic Field-Effect Transistors. Organic Electronics. 13(8): 1392-1400
Fahem, Z. And W. Bauhofer. 2012. Free Radical Fast Photo-Cured Gate Dielectric For Top-Gate Polymer Field Effect Transistors. Organic Electronics.
Cosseddu, P., G. Tiddia, S. Milita, And A. Bonfiglio. 2013. Continuous Tuning Of The Mechanical Sensitivity Of Pentacene Otfts On Flexible Substrates: From Strain Sensors To Deformable Transistors. Organic Electronics. 14(1): 206-211
Ozen, C., M. Yurtsever, And T. Ozturk. 2011. A Theoretical Approach To The Formation Mechanism Of Diphenyldithieno[3,2-B:2′,3′-D]Thiophene From 1,8-Diketone, 4,5-Bis(Benzoylmethylthio)Thiophene: A DFT Study. Tetrahedron. 67(34): 6275-6280
Watanabe, M., T.-H. Chao, C.-T. Chien, S.-W. Liu, Y. J. Chang, K.-Y. Chen, And T. J. Chow. 2012. 2-Halo-Subsituted Tetracenes: Their Generation And Single Crystal OFET Characteristics. Tetrahedron Letters. 53(18): 2284-2287
Ruiz, D., M. C., F. J. RamÃrez, V. Hernández, J. Casado, F. EnrÃquez, And J. T. López Navarrete. 2005. Vibrational Dynamics Study Of The Effect Of The Substituents On The Î -Conjugation Of Different Bithiophene Molecules. Journal Of Molecular Structure. 744-747(0): 393-401
Lopata, K., R. Reslan, M. Kowalska, D. Neuhauser, N. Govind, And K. Kowalski. 2011. Excited-State Studies Of Polyacenes: A Comparative Picture Using EOMCCSD, CR-EOMCCSD(T), Range-Separated (LR/RT)-TDDFT, TD-PM3, And TD-ZINDO. Journal Of Chemical Theory And Computation. 7(11): 3686-3693
Jang, S., E. Hwang, Y. Lee, S. Lee, And J. H. Cho. 2015. Multifunctional Graphene Optoelectronic Devices Capable Of Detecting And Storing Photonic Signals. Nano Letters. 15(4): 2542-2547
Khodagholy, D., T. Doublet, P. Quilichini, M. Gurfinkel, P. Leleux, A. Ghestem, E. Ismailova, T. Hervé, S. Sanaur, And C. Bernard. 2013. In Vivo Recordings Of Brain Activity Using Organic Transistors. Nature Communications. 4: 1575
Pan, X. M., L. L. Cui, L. L. Lui, G. C. Yang, Z. M. Su, And R. S. Wang. 2008. Theoretical Study On The Electronic Structures And Optical Properties Of Oxadisilole-Substituted Acenes. Chemical Physics Letters. 466(1-3): 37-43
Zhang, F. P., C. Melzer, A. Gassmann, H. Von Seggern, T. Schwalm, C. Gawrisch, And M. Rehahn. 2013. High-Performance N-Channel Thin-Film Transistors With Acene-Based Semiconductors. Organic Electronics. 14(3): 888-896
Enchev, V., V. Monev, N. Markova, M. Rogozherov, S. Angelova, And M. Spassova. 2013. A Model System With Intramolecular Hydrogen Bonding: Effect Of External Electric Field On The Tautomeric Conversion And Electronic Structures. Computational And Theoretical Chemistry. 1006: 113-122
Anthony, J. E. 2008. The Larger Acenes: Versatile Organic Semiconductors. Angewandte Chemie International Edition. 47(3): 452-483
Li, J. And Q. Zhang. 2015. Linearly Fused Azaacenes: Novel Approaches And New Applications Beyond Field-Effect Transistors (Fets). ACS Appl Mater Interfaces.
Zhang, L., A. Fonari, Y. Liu, A.-L. M. Hoyt, H. Lee, D. Granger, S. Parkin, T. P. Russell, J. E. Anthony, J.-L. Brédas, V. Coropceanu, And A. L. Briseno. 2014. Bistetracene: An Air-Stable, High-Mobility Organic Semiconductor With Extended Conjugation. Journal Of The American Chemical Society. 136(26): 9248-9251
GarcÃa, G., M. Moral, A. Garzón, J. M. Granadino-Roldán, A. Navarro, And M. Fernández-Gómez. 2012. Poly(Arylenethynyl-Thienoacenes) As Candidates For Organic Semiconducting Materials. A DFT Insight. Organic Electronics. 13(12): 3244-3253
Garzón, A., J. M. Granadino-Roldán, M. Moral, G. GarcÃa, M. P. Fernández-Liencres, A. Navarro, T. Peña-Ruiz, And M. Fernández-Gómez. 2010. Density Functional Theory Study Of The Optical And Electronic Properties Of Oligomers Based On Phenyl-Ethynyl Units Linked To Triazole, Thiadiazole, And Oxadiazole Rings To Be Used In Molecular Electronics. The Journal Of Chemical Physics. 132: 064901
Wang, J., H. Xu, B. Li, X.-P. Cao, And H.-L. Zhang. 2012. Synthesis And Characterization Of New Planar Butterfly-Shaped Fused Oligothiophenes. Tetrahedron. 68(4): 1192-1197
Katsuta, S., D. Miyagi, H. Yamada, T. Okujima, S. Mori, K.-I. Nakayama, And H. Uno. 2011. Synthesis, Properties, And Ambipolar Organic Field-Effect Transistor Performances Of Symmetrically Cyanated Pentacene And Naphthacene As Air-Stable Acene Derivatives. Organic Letters. 13(6): 1454-1457
Pramanik, C. And G. P. Miller. 2012. An Improved Synthesis Of Pentacene: Rapid Access To A Benchmark Organic Semiconductor. Molecules. 17(4): 4625-4633
Tang, M. L. And Z. Bao. 2010. Halogenated Materials As Organic Semiconductors†. Chemistry Of Materials. 23(3): 446-455
Tirado-Rives, J. And W. L. Jorgensen. 2008. Performance Of B3LYP Density Functional Methods For A Large Set Of Organic Molecules. Journal Of Chemical Theory And Computation. 4(2): 297-306
Bauschlicher, C. W. And H. Partridge. 1995. The Sensitivity Of B3LYP Atomization Energies To The Basis Set And A Comparison Of Basis Set Requirements For CCSD (T) And B3LYP. Chemical Physics Letters. 240(5): 533-540
Lee, C., W. Yang, And R. G. Parr. 1988. Development Of The Colle-Salvetti Correlation-Energy Formula Into A Functional Of The Electron Density. Physical Review B. 37(2): 785-789
Becke, A. D. 1993. Densityâ€Functional Thermochemistry. III. The Role Of Exact Exchange. The Journal Of Chemical Physics. 98(7): 5648-5652
Watanabe, M., K.-Y. Chen, Y. J. Chang, And T. J. Chow. 2013. Acenes Generated From Precursors And Their Semiconducting Properties. Accounts Of Chemical Research. 46(7): 1606-1615
Aprà , E., E. J. Bylaska, D. J. Dean, A. Fortunelli, F. Gao, P. S. Krstić, J. C. Wells, And T. L. Windus. 2003. Nwchem For Materials Science. Computational Materials Science. 28(2): 209-221
Valiev, M., E. J. Bylaska, N. Govind, K. Kowalski, T. P. Straatsma, H. J. J. Van Dam, D. Wang, J. Nieplocha, E. Apra, T. L. Windus, And W. A. De Jong. 2010. Nwchem: A Comprehensive And Scalable Open-Source Solution For Large Scale Molecular Simulations. Computer Physics Communications. 181(9): 1477-1489
Noordik, G. S. A. J. H. 2000. Molden: A Pre- And Post-Processing Program For Molecular And Electronic Structures. J. Comput.-Aided Mol. Design. 14: 123-134
Zhao, H., J. Zhou, L. Hu, And Q. Teng. 2009. Theoretical Studies On Electronic Structures And NMR Spectra Of Oligo(4-Vinylpyridine). Chinese Journal Of Chemistry. 27(9): 1687-1691
Yang, L., J.-K. Feng, And A.-M. Ren. 2006. Structural, Electronic And Optical Properties Of A Series Of Oligofluorene–Thiophene Oligomers And Polymers. Journal Of Molecular Structure: THEOCHEM. 758(1): 29-39
Musa, A., M. Saeed, A. Shaari, R. Sahnoun, And M. Lawal. 2014. Effects Of Delocalised Î -Electrons Around The Linear Acenes Ring (N= 1 To 7): An Electronic Properties Through DFT And Quantum Chemical Descriptors. Molecular Physics. (Ahead-Of-Print): 1-12
York, A. J., Glenn. 2012. Modeling And Simulation Of Heterogeneous Catalytic Reactions: From The Molecular Process To The Technical System. Platinum Metals Review. 56(3): 162-164
Thanikaivelan, P., V. Subramanian, J. Raghava Rao, And B. Unni Nair. 2000. Application Of Quantum Chemical Descriptor In Quantitative Structure Activity And Structure Property Relationship. Chemical Physics Letters. 323(1-2): 59-70
Parthasarathi, R., V. Subramanian, And P. K. Chattaraj. 2003. Effect Of Electric Field On The Global And Local Reactivity Indices. Chemical Physics Letters. 382(1-2): 48-56
Raya, A., C. Barrientos-Salcedo, C. Rubio-Póo, And C. Soriano-Correa. 2011. Electronic Structure Evaluation Through Quantum Chemical Descriptors Of 17β-Aminoestrogens With An Anticoagulant Effect. European Journal of Medicinal Chemistry. 46(6): 2463-2468
Abduljalil, M. S. M. a. H. M. 2012. Density Functional Theory Investigation of the Cyclobutane Molecules. British Journal of Science. 6 (1): 15-21
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