First principles investigations of geometric, electronic and optical properties of 5-aminotetrazole derivatives
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- 作者：Ayyaz Mahmood (1)
Ahmad Irfan (2) - 关键词：DFT ; Tetrazole ; Geometric and electronic properties ; Absorption spectra
- 刊名：Journal of Computational Electronics
- 出版年：2013
- 出版时间：September 2013
- 年：2013
- 卷：12
- 期：3
- 页码：437-447
- 全文大小：1277KB
- 参考文献：1. Koch, W., Holthausen, M.C.: A Chemist’s Guide to Density Functional Theory. Wiley-VCH, Weinheim (2000)
2. Hohenberg, P., Kohn, W.: Inhomogeneous electron gas. Phys. Rev. 136, B864–B871 (1964) CrossRef
3. Benson, F.R.: The chemistry of the tetrazoles. Chem. Rev. 41, 1-1 (1947) CrossRef
4. Akira, K., Takeshi, H.: Sakai Chem. Industry Co. Ltd. Japan. Kokai 7362, 634 CI 12A 82 (1973)
5. Koldobskii, G.I., Ostrovskii, V.A., Popavskii, V.S.: Advances in the chemistry of tetrazoles. Chem. Heterocycl. Compd. 17, 965-88 (1981) CrossRef
6. Chen, Z.X., Xiao, J.M., Xiao, H.M., Chiu, Y.N.: Studies on heats of formation for tetrazole derivatives with density functional theory B3LYP method. J. Phys. Chem. A 103, 8062-066 (1999) CrossRef
7. Sadlej-Sosnowska, N.: Application of natural bond orbital analysis to delocalization and aromaticity in C-substituted tetrazoles. J.?Org. Chem. 66, 8737-743 (2001) CrossRef
8. Alkorta, I., Elguero, J.: A theoretical study on the tautomerism of C-carboxylic and methoxycarbonyl substituted azoles. Struct. Chem. 16, 507-14 (2005) CrossRef
9. Irfan, A., Cui, R., Zhang, J., Hao, L.: Push–pull effect on the charge transfer, and tuning of emitting color for disubstituted derivatives of mer-Alq3. Chem. Phys. 364, 39-5 (2009) CrossRef
10. Kiselev, V.G., Gritsan, N.P.: Theoretical study of the 5-aminotetrazole thermal decomposition. J. Phys. Chem. A 113, 3677-684 (2009) CrossRef
11. Zhu, W., Xiao, H.: First-principles study of electronic structure, absorption spectra, and thermodynamic properties of crystalline 1 / H-tetrazole and its substituted derivatives. Struct. Chem. 21, 847-54 (2010) CrossRef
12. Pagacz-Kostrzewa, M., Reva, I.D., Bronisz, R., Giuliano, B.M., Fausto, R., Wierzejewska, M.: Conformational behavior and tautomer selective photochemistry in low temperature matrices: the case of 5-(1 / H-tetrazol-1-yl)-1,2,4-triazole. J. Phys. Chem. A 115, 5693-707 (2011) CrossRef
13. Ghule, V.D., Radhakrishnan, S., Jadhav, P.M.: Computational studies on tetrazole derivatives as potential high energy materials. Struct. Chem. 22, 775-82 (2011) CrossRef
14. Ravi, P., Surya, T.: A DFT study on the structure–property relationship of amino-, nitro- and nitrosotetrazoles, and their N-oxides: new high energy density molecules. Struct. Chem. 23, 487-98 (2012) CrossRef
15. Burn, P.L., Samuel, I.D.W., Lo, S.-C.: Organic phosphorescent material and organic optoelectronic device. Patent US2010/0096983 A1, 2010
16. Cojocaru, P., Magagnin, L., Cavallotti, P.L.: Effect of 5-phenyl-1 / H-tetrazole on copper dissolution for e-CMP. ECS Trans. 25, 65-9 (2010) CrossRef
17. Pan, J., Parham, A.H.: Organic ionic compounds, compositions and electronic devices. Patent US 7935961 B2, 2011
18. Werrett, M.V., Chartrand, D., Gale, J.D., Hanan, G.S., MacLellan, J.G., Massi, M., Muzzioli, S., Raiteri, P., Skelton, B.W., Silberstein, M., Stagni, S.: Synthesis, structural and photophysical investigation of diimine triscarbonyl Re(I) tetrazolato complexes. Inorg. Chem. 50, 1229-241 (2011) CrossRef
19. MaGee, K.D.M., Wright, P.J., Muzzioli, S., Siedlovskas, C., Raiteri, P., Baker, M.V., Brown, D.H., Stagni, S., Massi,?M.: Enhanced deep-blue emission from Pt(II) complexes bound to 2-pyridyltetrazolate and an ortho-xylene-linked bis(NHC)cyclophane. Dalton Trans. 42, 4233-236 (2013) CrossRef
20. D’Alessio, D., Muzzioli, S., Skelton, B.W., Stagni, S., Massi, M., Ogden, M.I.: Luminescent lanthanoid complexes of a tetrazole-functionalised calix[4]arene. Dalton Trans. 41, 4736-739 (2012) CrossRef
21. Shahroosvand, H., Najafi, L., Mohajerani, E., Khabbazi, A., Nasrollahzadeh, M.: Green, near-infrared electroluminescence of novel yttrium tetrazole complexes. J. Mater. Chem. C 1, 1337-344 (2013) CrossRef
22. Irfan, A., Al-Sehemi, A.G., Asiri, A.M., Nadeem, M., Alamry, K.A.: A study on the electronic and charge transfer properties in tin phthalocyanine (SnPc) derivatives by density functional theory. Comput. Theor. Chem. 977, 9-2 (2011) CrossRef
23. Irfan, A., Al-Sehemi, A.G., Muhammad, S., Zhang, J.: Packing effect on the transfer integrals and mobility in / α, / α-bis(dithieno[3,2- / b:2-3- / d]thiophene) (BDT) and its heteroatom-substituted analogues. Aust. J. Chem. 64, 1587-592 (2011) CrossRef
24. Irfan, A., Al-Sehemi, A.G., Asiri, A.M.: Donor-enhanced bridge effect on the electronic properties of triphenylamine based dyes: density functional theory investigations. J. Mol. Model. 18, 3609-615 (2012) CrossRef
25. Al-Sehemi, A.G., Irfan, A., Asiri, A.M.: The DFT investigations of the electron injection in hydrazone-based sensitizers. Theor. Chem. Acc. 131, 1199 (2012) CrossRef
26. Jin, R., Irfan, A.: Theoretical study of coumarin derivatives as chemosensors for fluoride anion. Comput. Theor. Chem. 986, 93-8 (2012) CrossRef
27. Irfan, A., Hina, N., Al-Sehemi, A.G., Asiri, A.M.: Quantum chemical investigations aimed at modeling highly efficient zinc porphyrin dye sensitized solar cells. J. Mol. Model. 18, 4199-207 (2012) CrossRef
28. Al-Sehemi, A.G., Irfan, A., El-Agrody, A.M.: Synthesis, characterization and DFT study of 4 / H-benzo[h]chromene derivatives. J.?Mol. Struct. 1018, 171-75 (2012) CrossRef
29. Irfan, A., Al-Sehemi, A.G.: Quantum chemical study in the direction to design efficient donor-bridge-acceptor triphenylamine sensitizers with improved electron injection. J. Mol. Model. 18, 4893-900 (2012) CrossRef
30. Irfan, A., Ijaz, F., Al-Sehemi, A.G., Asiri, A.M.: Quantum chemical approach toward rational designing of highly efficient oxadiazole based oligomers used in organic field effect transistors. J.?Comput. Electron. 11, 374-84 (2012) CrossRef
31. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A. Jr., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., Fox, D.J.: Gaussian. Gaussian, Inc., Wallingford, CT (2009)
32. Becke, A.D.: Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98, 5648-652 (1993) CrossRef
33. Miehlich, B., Savin, A., Stoll, H., Preuss, H.: Results obtained with the correlation energy density functionals of becke and Lee, Yang and Parr. Chem. Phys. Lett. 157, 200-06 (1989) CrossRef
34. Lee, C., Yang, W., Parr, R.G.: Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys. Rev. B 37, 785-89 (1988) CrossRef
35. Xu, W., Peng, B., Chen, J., Liang, M., Cai, F.: New triphenylamine-based dyes for dye-sensitized solar cells. J. Phys. Chem. C 112, 874-80 (2008) CrossRef
36. McLean, D., Chandler, G.S.: Contracted Gaussian-basis sets for molecular calculations. 1. 2nd row atoms, / Z=11-8. J. Chem. Phys. 72, 5639-648 (1980) CrossRef
37. Raghavachari, K., Binkley, J.S., Seeger, R., Pople, J.A.: Self-consistent molecular orbital methods. 20. Basis set for correlated wave-functions. J. Chem. Phys. 72, 650-54 (1980) CrossRef
38. Mahmood, A., Khan, I.U., Arshad, M.N., Ahmed, J.: / N-[Amino(azido)methylidene]-4-methylbenzenesulfonamide. Acta Crystallogr., Sect. E 67, o2140 (2011) CrossRef
39. Khan, I.U., Mahmood, A., Arshad, M.N.: 1-azido- / N-(phenylsulfonyl)-methanimidamide. Acta Crystallogr., Sect. E 67, o2703 (2011) CrossRef - 作者单位：Ayyaz Mahmood (1)
Ahmad Irfan (2)
1. Department of Fundamental Chemistry, Federal University of Pernambuco, Recife, PE, 50670-901, Brazil
2. Department of Chemistry, Faculty of Science, King Khalid University, P.O. Box 9004, Abha, 61413, Saudi Arabia
文摘
Density functional theory (DFT) is an important computational technique to study and predict the properties of isolated molecules. It is now a leading method for electronic structure calculations in chemistry and solid state physics. In this paper, we have investigated the geometric, electronic and optical properties of six 5-aminotetrazole derivatives employing DFT. The ground state geometries were optimized at B3LYP/6-311G?? and B3LYP/6-31G?? level of theories. The density of states, HOMOs and LUMOs and absorption spectra of all the compounds under study have been computed and discussed. The HOMOs are delocalized on aminotetrazole moiety in all the compounds. A comprehensible intra charge transfer has been observed from aminotetrazole moiety to entire compounds. In the absorption spectra, the wavelength of maximum absorption for triplets in all the systems is red shifted relative to their corresponding singlet wavelengths of absorption maximum. The B3LYP/6-311G?? level of theory is found to give better results than B3LYP/6-31G?? level of theory, to reproduce previously reported experimental data. In most of the cases B3LYP/6-31G?? level of theory overestimate more the bond lengths.