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Title: Quantitative analysis of intermolecular interactions in orthorhombic rubrene

Abstract

Rubrene is one of the most studied organic semiconductors to date due to its high charge carrier mobility which makes it a potentially applicable compound in modern electronic devices. Previous electronic device characterizations and first principles theoretical calculations assigned the semiconducting properties of rubrene to the presence of a large overlap of the extended π-conjugated core between molecules. We present here the electron density distribution in rubrene at 20 K and at 100 K obtained using a combination of high-resolution X-ray and neutron diffraction data. The topology of the electron density and energies of intermolecular interactions are studied quantitatively. Specifically, the presence of Cπ...Cπinteractions between neighbouring tetracene backbones of the rubrene molecules is experimentally confirmed from a topological analysis of the electron density, Non-Covalent Interaction (NCI) analysis and the calculated interaction energy of molecular dimers. A significant contribution to the lattice energy of the crystal is provided by H—H interactions. The electron density features of H—H bonding, and the interaction energy of molecular dimers connected by H—H interaction clearly demonstrate an importance of these weak interactions in the stabilization of the crystal structure. Finally, the quantitative nature of the intermolecular interactions is virtually unchanged between 20 K and 100 Kmore » suggesting that any changes in carrier transport at these low temperatures would have a different origin. The obtained experimental results are further supported by theoretical calculations.« less

Authors:
 [1];  [1];  [1];  [1];  [2];  [2];  [3];  [1];  [1]
+ Show Author Affiliations
  1. Aarhus Univ. (Denmark). Center for Materials Crystallography, Dept. of Chemistry and iNANO
  2. Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Chemical and Engineering Materials Division
  3. Japan Synchrotron Radiation Research Inst., Hyogo (Japan)
Publication Date:
Research Org.:
Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1294057
Grant/Contract Number:  
DNRF93; 2014A0078
Resource Type:
Accepted Manuscript
Journal Name:
IUCrJ
Additional Journal Information:
Journal Volume: 2; Journal Issue: 5; Journal ID: ISSN 2052-2525
Publisher:
International Union of Crystallography
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; electron density; rubrene; organic semiconductor; interaction energy

Citation Formats

Hathwar, Venkatesha R., Sist, Mattia, Jørgensen, Mads R. V., Mamakhel, Aref H., Wang, Xiaoping, Hoffmann, Christina M., Sugimoto, Kunihisa, Overgaard, Jacob, and Iversen, Bo Brummerstedt. Quantitative analysis of intermolecular interactions in orthorhombic rubrene. United States: N. p., 2015. Web. doi:10.1107/s2052252515012130.
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Hathwar, Venkatesha R., Sist, Mattia, Jørgensen, Mads R. V., Mamakhel, Aref H., Wang, Xiaoping, Hoffmann, Christina M., Sugimoto, Kunihisa, Overgaard, Jacob, & Iversen, Bo Brummerstedt. Quantitative analysis of intermolecular interactions in orthorhombic rubrene. United States. https://doi.org/10.1107/s2052252515012130
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Hathwar, Venkatesha R., Sist, Mattia, Jørgensen, Mads R. V., Mamakhel, Aref H., Wang, Xiaoping, Hoffmann, Christina M., Sugimoto, Kunihisa, Overgaard, Jacob, and Iversen, Bo Brummerstedt. Fri . "Quantitative analysis of intermolecular interactions in orthorhombic rubrene". United States. https://doi.org/10.1107/s2052252515012130. https://www.osti.gov/servlets/purl/1294057.
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@article{osti_1294057,
title = {Quantitative analysis of intermolecular interactions in orthorhombic rubrene},
author = {Hathwar, Venkatesha R. and Sist, Mattia and Jørgensen, Mads R. V. and Mamakhel, Aref H. and Wang, Xiaoping and Hoffmann, Christina M. and Sugimoto, Kunihisa and Overgaard, Jacob and Iversen, Bo Brummerstedt},
abstractNote = {Rubrene is one of the most studied organic semiconductors to date due to its high charge carrier mobility which makes it a potentially applicable compound in modern electronic devices. Previous electronic device characterizations and first principles theoretical calculations assigned the semiconducting properties of rubrene to the presence of a large overlap of the extended π-conjugated core between molecules. We present here the electron density distribution in rubrene at 20 K and at 100 K obtained using a combination of high-resolution X-ray and neutron diffraction data. The topology of the electron density and energies of intermolecular interactions are studied quantitatively. Specifically, the presence of Cπ...Cπinteractions between neighbouring tetracene backbones of the rubrene molecules is experimentally confirmed from a topological analysis of the electron density, Non-Covalent Interaction (NCI) analysis and the calculated interaction energy of molecular dimers. A significant contribution to the lattice energy of the crystal is provided by H—H interactions. The electron density features of H—H bonding, and the interaction energy of molecular dimers connected by H—H interaction clearly demonstrate an importance of these weak interactions in the stabilization of the crystal structure. Finally, the quantitative nature of the intermolecular interactions is virtually unchanged between 20 K and 100 K suggesting that any changes in carrier transport at these low temperatures would have a different origin. The obtained experimental results are further supported by theoretical calculations.},
doi = {10.1107/s2052252515012130},
journal = {IUCrJ},
number = 5,
volume = 2,
place = {United States},
year = {Fri Aug 14 00:00:00 EDT 2015},
month = {Fri Aug 14 00:00:00 EDT 2015}
}
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https://doi.org/10.1107/s2052252515012130
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Figures / Tables:

Figure 1 Figure 1: (a) ORTEP representation of the structure of rubrene at 100 K. Atom ellipsoids are shown at 50% probability level. The symmetry operations 2, m and i are superimposed on the molecule. (b) Molecular packing diagram with π•••π stacking along the b axis and interplanar distance between layers alongmore » the a-axis at 100 K. (c) Herringbone packing of molecules depicting C4•••H5 and C9•••H10 interactions (blue dotted lines), viewed along the a axis.« less
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    Towards the use of experimental electron densities to estimate reliable lattice energies
    journal, January 2018

    Confined toluene within InOF-1: CO 2 capture enhancement
    journal, January 2019

    • Garrido-Olvera, L. Pamela; Sanchez-Bautista, Jonathan E.; Alvarado-Alvarado, Daniel
    • RSC Advances, Vol. 9, Issue 56
    • DOI: 10.1039/c9ra05991a

    Water-mediated intermolecular interactions in 1,2- O -cyclohexylidene- myo -inositol: a quantitative analysis
    journal, January 2017

    • Purushothaman, Gayathri; Juvale, Kapil; Kirubakaran, Sivapriya
    • Acta Crystallographica Section C Structural Chemistry, Vol. 73, Issue 1
    • DOI: 10.1107/s2053229616018581

    Crystal structure and Hirshfeld surface analysis of diaquabis( N , N -diethylnicotinamide-κ N 1 )bis(2,4,6-trimethylbenzoato-κ O )manganese(II)
    journal, March 2018

    • Hökelek, Tuncer; Özkaya, Safiye; Necefoğlu, Hacali
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 74, Issue 4
    • DOI: 10.1107/s2056989018003377

    Crystal structure and Hirshfeld surface analysis of 2-oxo-13-epi-manoyl oxide isolated from Sideritis perfoliata
    journal, April 2018

    • Çelik, Ísmail; Atioğlu, Zeliha; Aksit, Huseyin
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 74, Issue 5
    • DOI: 10.1107/s2056989018005807

    Crystal structure and Hirshfeld surface analysis of 3,3′,3′′-[(1,3,5-triazine-2,4,6-triyl)tris(oxy)]tris(5,5-dimethylcyclohex-2-en-1-one)
    journal, June 2018

    • Atioğlu, Zeliha; Akkurt, Mehmet; Toze, Flavien A. A.
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 74, Issue 7
    • DOI: 10.1107/s2056989018009003

    Crystal structure and Hirshfeld surface analysis of ethane-1,2-diaminium 3-[2-(1,3-dioxo-1,3-diphenylpropan-2-ylidene)hydrazinyl]-5-nitro-2-oxidobenzenesulfonate dihydrate
    journal, June 2018

    • Atioğlu, Zeliha; Akkurt, Mehmet; Toze, Flavien A. A.
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 74, Issue 7
    • DOI: 10.1107/s2056989018009118

    Crystal structure and Hirshfeld surface analysis of dimethyl (3a S ,6 R ,6a S ,7 S )-2-(2,2,2-trifluoroacetyl)-2,3-dihydro-1 H ,6 H ,7 H -3a,6:7,9a-diepoxybenzo[ de ]isoquinoline-3a 1 ,6a-dicarboxylate
    journal, October 2018

    • Atioğlu, Zeliha; Akkurt, Mehmet; Toze, Flavien A. A.
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 74, Issue 11
    • DOI: 10.1107/s2056989018014305

    Crystal structure and Hirshfeld surface analysis of ethyl 2-{4-[(3-methyl-2-oxo-1,2-dihydroquinoxalin-1-yl)methyl]-1 H -1,2,3-triazol-1-yl}acetate
    journal, October 2018

    • Abad, Nadeem; Ramli, Youssef; Hökelek, Tuncer
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 74, Issue 11
    • DOI: 10.1107/s2056989018014561

    Crystal structure and Hirshfeld surface analysis of (4 Z )-1-butyl-4-(2-oxopropylidene)-2,3,4,5-tetrahydro-1 H -1,5-benzodiazepin-2-one
    journal, October 2018

    • Chkirate, Karim; Sebbar, Nada Kheira; Hökelek, Tuncer
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 74, Issue 11
    • DOI: 10.1107/s2056989018014779

    Crystal structure and Hirshfeld surface analysis of 1-{[2-oxo-3-(prop-1-en-2-yl)-2,3-dihydro-1 H -1,3-benzodiazol-1-yl]methyl}-3-(prop-1-en-2-yl)-2,3-dihydro-1 H -1,3-benzodiazol-2-one
    journal, November 2018

    • Saber, Asmaa; Sebbar, Nada Kheira; Hökelek, Tuncer
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 74, Issue 12
    • DOI: 10.1107/s2056989018015219

    Crystal structure and Hirshfeld surface analysis of 5-methyl-1,2,4-triazolo[1,5- a ]pyrimidine
    journal, November 2018

    • Lahmidi, Sanae; Sebbar, Nada Kheira; Hökelek, Tuncer
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 74, Issue 12
    • DOI: 10.1107/s2056989018016225

    Crystal structure and Hirshfeld surface analysis of 1-benzyl-3-(prop-2-yn-1-yl)-2,3-dihydro-1 H -1,3-benzodiazol-2-one
    journal, November 2018

    • Saber, Asmaa; Sebbar, Nada Kheira; Hökelek, Tuncer
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 74, Issue 12
    • DOI: 10.1107/s2056989018016298

    Crystal structure and Hirshfeld surface analysis of 3,4-dihydro-2-(2,4-dioxo-6-methylpyran-3-ylidene)-4-(4-pyridin-4-yl)-1,5-benzodiazepine
    journal, January 2019

    • El Ghayati, Lhoussaine; Ramli, Youssef; Hökelek, Tuncer
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 75, Issue 1
    • DOI: 10.1107/s2056989018017565

    Crystal structure and Hirshfeld surface analysis of ( E )-3-(2-chlorophenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one
    journal, January 2019

    • Murthy, T. N. Sanjeeva; Atioğlu, Zeliha; Akkurt, Mehmet
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 75, Issue 2
    • DOI: 10.1107/s2056989018018066

    Synthesis, crystal structure and Hirshfeld surface analysis of 3-(4,4-dimethyl-2,3,4,5-tetrahydro-1 H -1,5-benzodiazepin-2-ylidene)-6-methyl-3,4-dihydro-2 H -pyran-2,4-dione
    journal, January 2019

    • Samba, Mohamed; Minnih, Mohamed Said; Hökelek, Tuncer
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 75, Issue 2
    • DOI: 10.1107/s2056989019000689

    Crystal structure and Hirshfeld surface analysis of ( E )-1-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]-2-(4-fluorophenyl)diazene
    journal, January 2019

    • Atioğlu, Zeliha; Akkurt, Mehmet; Shikhaliyev, Namiq Q.
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 75, Issue 2
    • DOI: 10.1107/s2056989019000707

    Crystal structure, Hirshfeld surface analysis and DFT study of (2 Z )-2-(4-fluorobenzylidene)-4-(prop-2-yn-1-yl)-3,4-dihydro-2 H -1,4-benzothiazin-3-one
    journal, February 2019

    • Hni, Brahim; Sebbar, Nada Kheira; Hökelek, Tuncer
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 75, Issue 3
    • DOI: 10.1107/s2056989019002354

    Crystal structure and Hirshfeld surface analysis of dimethyl (1 R *,3a S *,3a 1 R *,6a S *,9 R *,9a S *)-3a 1 ,5,6,9a-tetrahydro-1 H ,4 H ,9 H -1,3a:6a,9-diepoxyphenalene-2,3-dicarboxylate
    journal, March 2019

    • Alekseeva, Kseniia A.; Raspertov, Pavel V.; Çelikesir, Sevim Türktekin
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 75, Issue 4
    • DOI: 10.1107/s2056989019003499

    Crystal structure, Hirshfeld surface analysis and DFT study of (2 Z )-2-(2,4-dichlorobenzylidene)-4-[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-3,4-dihydro-2 H -1,4-benzothiazin-3-one
    journal, April 2019

    • Hni, Brahim; Sebbar, Nada Kheira; Hökelek, Tuncer
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 75, Issue 5
    • DOI: 10.1107/s2056989019004250

    ( E )-1-(Benzo[ d ][1,3]dioxol-5-yl)-3-([2,2′-bithiophen]-5-yl)prop-2-en-1-one: crystal structure, UV–Vis analysis and theoretical studies of a new π-conjugated chalcone
    journal, April 2019

    • Anizaim, Ainizatul Husna; Zaini, Muhamad Fikri; Laruna, Muhammad Adlan
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 75, Issue 5
    • DOI: 10.1107/s2056989019004912

    Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 5,5-diphenyl-1,3-bis(prop-2-yn-1-yl)imidazolidine-2,4-dione
    journal, June 2019

    • Ghandour, Ismail; Bouayad, Abdelouahed; Hökelek, Tuncer
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 75, Issue 7
    • DOI: 10.1107/s2056989019007801

    Crystal and molecular structures of boldenone and four boldenone steroid esters
    journal, October 2019

    • Turza, Alexandru; Miclăuș, Maria O.; Pop, Aurel
    • Zeitschrift für Kristallographie - Crystalline Materials, Vol. 234, Issue 10
    • DOI: 10.1515/zkri-2019-0030

    The Elusive Structural Origin of Plastic Bending in Dimethyl Sulfone Crystals with Quasi‐isotropic Crystal Packing
    journal, May 2017

    • Thomas, Sajesh P.; Shi, Ming W.; Koutsantonis, George A.
    • Angewandte Chemie, Vol. 129, Issue 29
    • DOI: 10.1002/ange.201701972

    High-Temperature Crystal Structure and Chemical Bonding in Thermoelectric Germanium Selenide (GeSe)
    journal, April 2017

    • Sist, Mattia; Gatti, Carlo; Nørby, Peter
    • Chemistry - A European Journal, Vol. 23, Issue 28
    • DOI: 10.1002/chem.201700536

    Electron Density Studies in Materials Research
    journal, September 2019

    • Tolborg, Kasper; Iversen, Bo B.
    • Chemistry – A European Journal, Vol. 25, Issue 66
    • DOI: 10.1002/chem.201903087

    Crystal structure and Hirshfeld surface analysis of 1-[(1-butyl-1 H -1,2,3-triazol-4-yl)methyl]-3-methylquinoxalin-2(1 H )-one
    journal, November 2018

    • Abad, Nadeem; Ramli, Youssef; Hökelek, Tuncer
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 74, Issue 12
    • DOI: 10.1107/s205698901801589x

    Crystal structure and Hirshfeld surface analysis of ( E )-1-(4-chlorophenyl)-2-[2,2-dichloro-1-(4-fluorophenyl)ethenyl]diazene
    journal, March 2019

    • Shikhaliyev, Namiq Q.; Çelikesir, Sevim Türktekin; Akkurt, Mehmet
    • Acta Crystallographica Section E Crystallographic Communications, Vol. 75, Issue 4
    • DOI: 10.1107/s2056989019003657

    Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 5,5-diphenyl-1,3-bis(prop-2-yn-1-yl)imidazolidine-2,4-dione
    text, January 2019

    Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 5,5-diphenyl-1,3-bis(prop-2-yn-1-yl)imidazolidine-2,4-dione
    text, January 2019

    The Elusive Structural Origin of Plastic Bending in Dimethyl Sulfone Crystals with Quasi-isotropic Crystal Packing
    journal, May 2017

    • Thomas, Sajesh P.; Shi, Ming W.; Koutsantonis, George A.
    • Angewandte Chemie International Edition, Vol. 56, Issue 29
    • DOI: 10.1002/anie.201701972

    Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 5,5-diphenyl-1,3-bis(prop-2-yn-1-yl)imidazolidine-2,4-dione
    text, January 2019

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