Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Acta Chimica Slovaca

The Journal of Slovak University of Technology in Bratislava

2 Issues per year

Open Access
Online
ISSN
1337-978X
See all formats and pricing
More options …

Molecular orbital analysis of selected organic p-type and n-type conducting small molecules

Denisa Cagardová
  • Corresponding author
  • Department of Chemical Physics, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovakia
  • Email
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Vladimír Lukeš
  • Department of Chemical Physics, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovakia
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2017-06-23 | DOI: https://doi.org/10.1515/acs-2017-0002

Abstract

In this article, the selected series of commercially available p-type and n-type semiconducting small molecules are systematically studied by density functional theory using the B3LYP hybrid functional and 6-311G(2d,p) basis set. The optimal geometries of each molecule in the electronic neutral and corresponding charged states are calculated. The evaluated energies of frontier molecular orbitals and electronic band gaps are mutually compared together with adiabatic electronic intramolecular reorganization energies. The chemical accuracy of the evaluated theoretical quantities is estimated from the comparison with available experimental data.

Keywords: Aromatic structure; chemical structure; electron structure; molecular orbital; reorganization energy

References

  • Becke AD (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Phys. Rev. A 38: 3098-3100.CrossrefGoogle Scholar

  • Beu T, Onoe J, Hida A (2005) First-principles calculations of the electronic structure of one-dimensional C60 polymers. Phys. Rev. B 72: 155416.CrossrefGoogle Scholar

  • Brédas J-L, Beljonne D, Coropceanu V, Cornil J (2004) Charge-transfer and energy-transfer processes in pi-conjugated oligomers and polymers: a molecular picture. Chem. Rev. 104 (11): 4971.Google Scholar

  • Brütting W (2005) Organic Semiconductors. University of Augsburg, Germany.Google Scholar

  • Cornill J, Brédas J-L, Zaumseil J, Sirringhaus H (2007) Ambipolar transport in organic conjugated materials. Adv. Mat. 19 (14): 1791-1799.Google Scholar

  • Filo J, Putala M (2010) Semiconducting organic molecular materials. Journal of Electrical Engineering, Vol. 61, No. 5: 314-320.Google Scholar

  • Flukiger P, Luthi HP, Sortmann S, Weber J (2002) Molekel 4.3, Swiss NationalSupercomputing Centre, Manno, Switzerland.Google Scholar

  • Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery Jr. JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Keith T, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2010) Gaussian 09 Revision C.01, Gaussian, Inc., Wallingford, CT.Google Scholar

  • Hariharan PC, Pople JA (1973) The Influence of Polarization Functions on Molecular Orbital Hydrogenation Energies. Theoret. Chimica Acta 28: 213-222.CrossrefGoogle Scholar

  • Hohenberg P, Kohn W (1964) Inhomogeneous electron gas. Phys. Rev. 136: B864-B871.Google Scholar

  • Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B 37: 785-789.CrossrefGoogle Scholar

  • Marcus RA (1993) Electron transfer reactions in chemistry. Theory and experiment. Rev. Mod. Phys. 65: 599.CrossrefGoogle Scholar

  • McCormick TM, Bridges CR, Carrera EI, DiCarmine PM, Gibson GL, Hollinger J, Kozycz LM, Seferos DS (2013) Conjugated Polymers: Evaluating DFT Methods for More Accurate Orbital Energy Modeling. Macromolecules 46: 3879-3886.CrossrefWeb of ScienceGoogle Scholar

  • Norton JE, Brédas J-L (2008) Polarization energies in oligoacene semiconductor crystals. J. Am. Chem. Soc. 130 (37): 12377-84.Web of ScienceGoogle Scholar

  • Olivier Y, Lemaur V, Bredas J-L, Cornil J (2006) Charge Hopping in Organic Semiconductors: Influence of Molecular Parameters on Macroscopic Mobilities in Model One-Dimensional Stacks. J. Phys. Chem. A 110 (19): 6356.Google Scholar

  • Rassolov V, Pople JA, Ratner M, Windus TL (1998) 6-31G* basis set for atoms K through Zn. J. Chem. Phys. 109: 1223-1229.CrossrefGoogle Scholar

  • Reiss P, Couderc E, De Girolamo J, Pron A (2011) Conjugated polymers/semiconductor nanocrystals hybrid materials-preparation, electrical transport properties and applications. Nanoscale 3: 446-489.Google Scholar

  • Runge E, Gross EKU (1984) Density-Functional Theory for Time-Dependent Systems. Phys. Rev. Lett. 52: 997-1000.CrossrefWeb of ScienceGoogle Scholar

  • Sawadogo R, Diendéré F, Guiguemdé I, Ouédraogo R, Sotiropoulos J-M (2016) Semiconducting Oligomers of 1,4-dimethoxybenzene, Thiophene and Thiazole: A Theoretical Study. ACSJ 17(1): 1-10.Google Scholar

  • Sigma Aldrich (2017) Available on internet: http://www.sigmaaldrich.com/.Google Scholar

  • Wang L, Li P, Xu B, Zhang H, Tian W (2014) The substituent effect on charge transport property of triisopropylsilylethynyl anthracene derivatives. Org. Electron. 15: 2476-2485.CrossrefWeb of ScienceGoogle Scholar

  • Yin SW, Yi YP, Li QX, Yu G, Liu YG, Shuai YG (2006) Balanced Carrier Transports of Electrons and Holes in Silole-Based Compounds. A Theoretical Study. J. Phys. Chem. A. 110: 7138.CrossrefGoogle Scholar

  • Zahn DRT, Gavrila GN, Gorgoi M (2006) The transport gap of organic semiconductors studied using the combination of direct and inverse photoemission. Chem. Phys. 325 (1): 99-112.Google Scholar

About the article

Published Online: 2017-06-23

Published in Print: 2017-04-25


Citation Information: Acta Chimica Slovaca, Volume 10, Issue 1, Pages 6–16, ISSN (Online) 1337-978X, DOI: https://doi.org/10.1515/acs-2017-0002.

Export Citation

© Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava . This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License. BY-NC-ND 4.0

Comments (0)

Please log in or register to comment.
Log in