Tuning the Charge Transfer and Optoelectronic Properties of 4,6-Di(Thiophene-2-YL)Pyrimidine via Oligocenothiophene Substitution

• Autorzy: Irfan A. , Chaudhry A. R. , Al-Sehemi A. G. , Muhammad S. , Jin R. , Tang S.

Identyfikatory

DOI

10.24425/amm.2018.125086

• Języki publikacji: EN

Abstrakty

EN

Five new derivatives of 4,6-di(thiophen-2-yl)pyrimidine (DTP) were designed by structural modification with the aim to tune the electro-optical and charge transfer properties. The effect of oligocene and oligocenothiophene incorporation/substitution was investigated on various properties of interests. The smaller hole reorganization energy revealed that compounds 1-5 might be good hole transfer contenders. The smaller hole reorganization energy of newly designed five DTP derivatives than the pentacene showed that prior compounds might be good/comparable hole transfer materials than/to that of pentacene. The computed electron reorganization energy of DTP derivatives 1-5 are 124, 185, 93, 95 and 189 meV smaller than the meridional-tris (8-hydroxyquinoline) aluminum (mer-Alq3) illuminating that electron mobility of these derivatives might be better/comparable than/to referenced compound.

Słowa kluczowe

EN

organic semiconductors; oligocene; density functional theory; optoelectronic properties; charge transfer properties

• Wydawca: Institute of Metallurgy and Materials Science of Polish Academy of Sciences ; Committee of Materials Engineering and Metallurgy of Polish Academy of Sciences
• Czasopismo: Archives of Metallurgy and Materials
• Rocznik: 2018
• Tom: Vol. 63, iss. 4
• Strony: 1629--1636
• Opis fizyczny: Bibliogr. 44 poz., rys., tab., wzory

Twórcy

autor

Irfan A.

• King Khalid University, Faculty of Science, Department of Chemistry, Abha 61413, P.O. Box 9004, Saudi Arabia

autor

Chaudhry A. R.

• Deanship of Scientific Research, University of Bisha, Bisha 61922, P.O. Box 551, Saudi Arabia

autor

Al-Sehemi A. G.

• King Khalid University, Faculty of Science, Department of Chemistry, Abha 61413, P.O. Box 9004, Saudi Arabia

autor

Muhammad S.

• King Khalid University, Faculty of Science, Department of Physics, Abha 61413, P.O. Box 9004, Saudi Arabia

autor

Jin R.

• Chifeng University, College of Chemistry and Chemical Engineering, Chifeng 024000, China

autor

Tang S.

• Jilin Agriculture University, College of Life Science, China

Bibliografia

• [1] W. Li, Z. Wang, P. Lu, Opt. Mater. 26, 243 (2004).
• [2] S. Guang, S. Yin, H. Xu, W. Zhu, Y. Gao, Y. Song, Dyes Pigm. 73, 285 (2007).
• [3] M. Erouel, K. Diallo, J. Tardy, P. Blanchard, J. Roncali, P. Frère, N. Jaffrezic, Materials Science and Engineering: C 28, 965 (2008).
• [4] Y. Xiong, M. Wang, X. Qiao, J. Li, H. Li, Tetrahedron 71, 852 (2015).
• [5] A. Tigreros, A. Ortiz, B. Insuasty, Dyes Pigm. 111, 45 (2014).
• [6] P. Szlachcic, K. S. Danel, M. Gryl, K. Stadnicka, Z. Usatenko, N. Nosidlak, G. Lewińska, J. Sanetra, W. Kuźnik, Dyes Pigm. 114, 184 (2015).
• [7] S.-Y. Gwon, B. A. Rao, H.-S. Kim, Y.-A. Son, S.-H. Kim, Spectrochimica Acta A 144, 226 (2015).
• [8] X.-Q. Ran, J.-K. Feng, A.-M. Ren, W.-C. Li, L.-Y. Zou, C.-C. Sun, J. Phys. Chem. A 113, 7933 (2009).
• [9] A. Irfan, A. G. Al-Sehemi, S. Muhammad, Synth. Met. 190, 27 (2014).
• [10] A. Irfan, A. G. Al-Sehemi, M. S. Al-Assiri, J. Fluorine Chem. 157, 52 (2014).
• [11] J. Zhang, G. Wu, C. He, D. Deng, Y. Li, J. Mater. Chem. 21, 3768 (2011).
• [12] H. Minemawari, T. Yamada, H. Matsui, J.y. Tsutsumi, S. Haas, R. Chiba, R. Kumai, T. Hasegawa, Nature 475, 364 (2011).
• [13] D. H. Kim, Y. D. Park, Y. Jang, H. Yang, Y. H. Kim, J. I. Han, D. G. Moon, S. Park, T. Chang, C. Chang, M. Joo, C. Y. Ryu, K. Cho, Adv. Funct. Mater. 15, 77 (2005).
• [14] L. Wang, G. Nan, X. Yang, Q. Peng, Q. Li, Z. Shuai, Chem. Soc. Rev. 39, 423 (2010).
• [15] J. E. Anthony, Angew. Chem. Int. Ed. 47, 452 (2008).
• [16] J. E. Anthony, Chem. Rev. 106, 5028 (2006).
• [17] J. Mei, Y. Diao, A. L. Appleton, L. Fang, Z. Bao, J. Am. Chem. Soc. 135, 6724 (2013).
• [18] A. Irfan, A. Rasool Chaudhry, A. G. Al-Sehemi, M. Sultan Al-Asiri, S. Muhammad, A. Kalam, J. Saudi. Chem. Soc. 20, 336 (2016).
• [19] A. Irfan, A. Kalam, A. R. Chaudhry, A. G. Al-Sehemi, S. Muhammad, Optik - Intern. J. Light Elect. Optics 132, 101 (2017).
• [20] A. Irfan, A. G. Al-Sehemi, A. R. Chaudhry, S. Muhammad, Optik - Intern. J. Light Elect. Optics 138, 349 (2017).
• [21] W. Kohn, A. D. Becke, R. G. Parr, J. Phys. Chem. 100, 12974 (1996).
• [22] A. D. Becke, J. Chem. Phys. 98, 5648 (1993).
• [23] R. S. Sánchez-Carrera, V. Coropceanu, D. A. da Silva Filho, R. Friedlein, W. Osikowicz, R. Murdey, C. Suess, W. R. Salaneck, J.-L. Brédas, J. Phys. Chem. B 110, 18904 (2006).
• [24] C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 37, 785 (1988).
• [25] G. A. Petersson, A. Bennett, T. G. Tensfeldt, M. A. Al-Laham, W. A. Shirley, J. Mantzaris, J. Chem. Phys. 89, 2193 (1988).
• [26] F. Furche, R. Ahlrichs, J. Chem. Phys. 117, 7433 (2002).
• [27] A. Irfan, A. G. Al-Sehemi, S. Muhammad, A. R. Chaudhry, M. S. Al-Assiri, R. Jin, A. Kalam, M. Shkir, A. M. Asiri, Comptes Rendus Chimie (2015).
• [28] C. Zhang, W. Liang, H. Chen, Y. Chen, Z. Wei, Y. Wu, J. Mol. Struct. (TheoChem) 862, 98 (2008).
• [29] A. R. Chaudhry, R. Ahmed, A. Irfan, A. Shaari, A. G. Al-Sehemi, Mater. Chem. Phys. 138, 468 (2013).
• [30] R. A. Marcus, N. Sutin, Biochim. Biophys. Acta - Rev. Bioenerg. 811, 265 (1985).
• [31] E. V. Tsiper, Z. G. Soos, W. Gao, A. Kahn, Chem. Phys. Lett. 360, 47 (2002).
• [32] J. L. Brédas, J. P. Calbert, D. A. da Silva Filho, J. Cornil, Proc. Natl. Acad. Sci. 99, 5804 (2002).
• [33] R. Jin, A. Irfan, RSC Advances 7, 39899 (2017).
• [34] A. Irfan, A. R. Chaudhry, S. Muhammad, A. G. Al-Sehemi, J. Mol. Graphics Modell. 75, 209 (2017).
• [35] S. H. Frisch MJ, et al., in, Gaussian 09, Revision A. 01 Gaussian Inc., Wallingford, CT, 2009.
• [36] S. Muhammad, A. R. Chaudhry, A. Irfan, A. G. Al-Sehemi, RSC Advances 7, 36632 (2017).
• [37] G. S. H. S. Dufresne, W. G. Skene, J. Phys. Chem. B 111, 11407 (2007).
• [38] R. A. Marcus, Rev. Mod. Phys. 65, 599 (1993).
• [39] N. E. Gruhn, D. A. da Silva Filho, T. G. Bill, M. Malagoli, V. Coropceanu, A. Kahn, J.-L. Brédas, J. Am. Chem. Soc. 124, 7918 (2002).
• [40] S. T. Bromley, M. Mas-Torrent, P. Hadley, C. Rovira, J. Am. Chem. Soc. 126, 6544 (2004).
• [41] A. Irfan, R. Cui, J. Zhang, L. Hao, Chem. Phys. 364, 39 (2009).
• [42] P. Politzer , D. G. Truhlar (Eds.), Plenum Press, New York (1981).
• [43] R. F. Stewart, Chem. Phys. Lett. 65, 335 (1979).
• [44] J. S. Murray , P. Politzer, WIRES Comput. Mol. Sci. 1, 153 (2011).

Uwagi

EN

1. The authors extend their appreciation to the Deanship of Scientific Research at King Khalid University for funding this work through research groups program under grant number R.G.P.1/18/38. A. R. C. is grateful to University of Bisha (UB) for providing the support and facilities to complete the research study.

PL

2. Opracowanie rekordu w ramach umowy 509/P-DUN/2018 ze środków MNiSW przeznaczonych na działalność upowszechniającą naukę (2018).