Search Menu
DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information
Search Scholarly Publications

Title: Density functional study of the electronic structure of dye-functionalized fullerenes and their model donor-acceptor complexes containing P3HT

Abstract

Here, we study the electronic structure of C60 fullerenes functionalized with a thiophene-diketopyrrolopyrrole-thiophene based chromophore using density functional theory combined with large polarized basis sets. As the attached chromophore has electron donor character, the functionalization of the fullerene leads to a donor-acceptor (DA) system. We examine in detail the effect of the linker and the addition site on the electronic structure of the functionalized fullerenes. We further study the electronic structure of these DA complexes with a focus on the charge transfer excitations. Finally, we examine the interface of the functionalized fullerenes with the widely used poly(3-hexylthiophene-2,5-diyl) (P3HT) donor. Our results show that all functionalized fullerenes with an exception of the C60-pyrrolidine [6,6], where the pyrrolidine is attached at a [6,6] site, have larger electron affinities relative to the pristine C60 fullerene. We also estimate the quasi-particle gap, lowest charge transfer excitation energy, and the exciton binding energies of the functionalized fullerene-P3MT model systems. Results show that the exciton binding energies in these model complexes are slightly smaller compared to a similarly prepared phenyl-C61-butyric acid methyl ester (PCBM)-P3MT complex.

Authors:
 [1];  [1];  [1];  [1];  [1]
+ Show Author Affiliations
  1. Univ. of Texas, El Paso, TX (United States). Dept. of Physics
Publication Date:
Research Org.:
Univ. of Texas at El Paso, TX (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)
Contributing Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). National Energy Research Scientific Computing Center (NERSC)
OSTI Identifier:
1469583
Alternate Identifier(s):
OSTI ID: 1246532
Grant/Contract Number:  
SC0006818; SC0002168; DMR-1205302; TG-DMR090071
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Chemical Physics
Additional Journal Information:
Journal Volume: 144; Journal Issue: 14; Journal ID: ISSN 0021-9606
Publisher:
American Institute of Physics (AIP)
Country of Publication:
United States
Language:
English
Subject:
74 ATOMIC AND MOLECULAR PHYSICS; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; chemical compounds and components; electrochemistry; chemical elements; fullerenes; electronic structure; excitation energies; bond length; excitons; leptons; density functional theory

Citation Formats

Baruah, Tunna, Garnica, Amanda, Paggen, Marina, Basurto, Luis, and Zope, Rajendra R. Density functional study of the electronic structure of dye-functionalized fullerenes and their model donor-acceptor complexes containing P3HT. United States: N. p., 2016. Web. doi:10.1063/1.4944469.
Copy to clipboard
Baruah, Tunna, Garnica, Amanda, Paggen, Marina, Basurto, Luis, & Zope, Rajendra R. Density functional study of the electronic structure of dye-functionalized fullerenes and their model donor-acceptor complexes containing P3HT. United States. https://doi.org/10.1063/1.4944469
Copy to clipboard
Baruah, Tunna, Garnica, Amanda, Paggen, Marina, Basurto, Luis, and Zope, Rajendra R. Fri . "Density functional study of the electronic structure of dye-functionalized fullerenes and their model donor-acceptor complexes containing P3HT". United States. https://doi.org/10.1063/1.4944469. https://www.osti.gov/servlets/purl/1469583.
Copy to clipboard
@article{osti_1469583,
title = {Density functional study of the electronic structure of dye-functionalized fullerenes and their model donor-acceptor complexes containing P3HT},
author = {Baruah, Tunna and Garnica, Amanda and Paggen, Marina and Basurto, Luis and Zope, Rajendra R.},
abstractNote = {Here, we study the electronic structure of C60 fullerenes functionalized with a thiophene-diketopyrrolopyrrole-thiophene based chromophore using density functional theory combined with large polarized basis sets. As the attached chromophore has electron donor character, the functionalization of the fullerene leads to a donor-acceptor (DA) system. We examine in detail the effect of the linker and the addition site on the electronic structure of the functionalized fullerenes. We further study the electronic structure of these DA complexes with a focus on the charge transfer excitations. Finally, we examine the interface of the functionalized fullerenes with the widely used poly(3-hexylthiophene-2,5-diyl) (P3HT) donor. Our results show that all functionalized fullerenes with an exception of the C60-pyrrolidine [6,6], where the pyrrolidine is attached at a [6,6] site, have larger electron affinities relative to the pristine C60 fullerene. We also estimate the quasi-particle gap, lowest charge transfer excitation energy, and the exciton binding energies of the functionalized fullerene-P3MT model systems. Results show that the exciton binding energies in these model complexes are slightly smaller compared to a similarly prepared phenyl-C61-butyric acid methyl ester (PCBM)-P3MT complex.},
doi = {10.1063/1.4944469},
journal = {Journal of Chemical Physics},
number = 14,
volume = 144,
place = {United States},
year = {Fri Apr 08 00:00:00 EDT 2016},
month = {Fri Apr 08 00:00:00 EDT 2016}
}
Copy to clipboard
Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1063/1.4944469
Copyright Statement
Other availability
Search WorldCat Search WorldCat to find libraries that may hold this journal
Citation Metrics:
Cited by: 7 works
Citation information provided by
Web of Science
Save / Share:
Export Metadata
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.

Works referenced in this record:

Semiconducting polymers (as donors) and buckminsterfullerene (as acceptor): photoinduced electron transfer and heterojunction devices
journal, August 1993

Generalized Gradient Approximation Made Simple
journal, October 1996

  • Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias
  • Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868
  • DOI: 10.1103/PhysRevLett.77.3865

Bulk Heterojunction Solar Cells with Large Open-Circuit Voltage: Electron Transfer with Small Donor-Acceptor Energy Offset
journal, March 2011

  • Gong, Xiong; Tong, Minghong; Brunetti, Fulvio G.
  • Advanced Materials, Vol. 23, Issue 20
  • DOI: 10.1002/adma.201003768

Electron deficient diketopyrrolopyrrole dyes for organic electronics: synthesis by direct arylation, optoelectronic characterization, and charge carrier mobility
journal, January 2014

  • Hendsbee, Arthur D.; Sun, Jon-Paul; Rutledge, Lesley R.
  • J. Mater. Chem. A, Vol. 2, Issue 12
  • DOI: 10.1039/c3ta14414c

Why Do Cycloaddition Reactions Involving C 60 Prefer [6,6] over [5,6] Bonds?
journal, April 2013

  • Fernández, Israel; Solà, Miquel; Bickelhaupt, F. Matthias
  • Chemistry - A European Journal, Vol. 19, Issue 23
  • DOI: 10.1002/chem.201300648

Addition reactions of C60 leading to fulleroprolines
journal, January 1994

  • Maggini, Michele; Scorrano, Gianfranco; Bianco, Alberto
  • Journal of the Chemical Society, Chemical Communications, Issue 3
  • DOI: 10.1039/c39940000305

Fullerene derivative acceptors for high performance polymer solar cells
journal, January 2011

  • He, Youjun; Li, Yongfang
  • Phys. Chem. Chem. Phys., Vol. 13, Issue 6
  • DOI: 10.1039/C0CP01178A

Valence isomerism and rearrangements in methanofullerenes
journal, January 1994

  • Diederich, Fran�ois; Isaacs, Lyle; Philp, Douglas
  • Journal of the Chemical Society, Perkin Transactions 2, Issue 3
  • DOI: 10.1039/p29940000391

PCBM Disperse-Red Ester with Strong Visible-Light Absorption: Implication of Molecular Design and Morphological Control for Organic Solar Cells
journal, December 2011

  • Wang, Mingfeng; Chesnut, Eneida; Sun, Yanming
  • The Journal of Physical Chemistry C, Vol. 116, Issue 1
  • DOI: 10.1021/jp209782c

An unprecedented [5,6]-open adduct via a direct benzyne-C60 cycloaddition
journal, September 2013

The influence of materials work function on the open circuit voltage of plastic solar cells
journal, February 2002

Comparative Photophysics of C 61 H 2 Isomers †
journal, December 2003

  • Anthony, Stephen M.; Bachilo, Sergei M.; Weisman, R. Bruce
  • The Journal of Physical Chemistry A, Vol. 107, Issue 49
  • DOI: 10.1021/jp035085f

Narrow‐Bandgap Diketo‐Pyrrolo‐Pyrrole Polymer Solar Cells: The Effect of Processing on the Performance
journal, July 2008

  • Wienk, Martijn M.; Turbiez, Mathieu; Gilot, Jan
  • Advanced Materials, Vol. 20, Issue 13, p. 2556-2560
  • DOI: 10.1002/adma.200800456

Diketopyrrolopyrrole (DPP)-based materials for organic photovoltaics
journal, January 2012

Design, Synthesis, and Self-assembly of Oligothiophene Derivatives with a Diketopyrrolopyrrole Core
journal, September 2008

  • Tamayo, Arnold Bernarte; Tantiwiwat, Mananya; Walker, Bright
  • The Journal of Physical Chemistry C, Vol. 112, Issue 39
  • DOI: 10.1021/jp804816c

Oligothiophene Derivatives Functionalized with a Diketopyrrolopyrrolo Core for Solution-Processed Field Effect Transistors: Effect of Alkyl Substituents and Thermal Annealing
journal, October 2008

  • Tantiwiwat, Mananya; Tamayo, Arnold; Luu, Ngoc
  • The Journal of Physical Chemistry C, Vol. 112, Issue 44
  • DOI: 10.1021/jp8068305

The effect of thiophene substituents of fulleropyrrolidine acceptors on the performance of inverted organic solar cells
journal, September 2014

[60]Fulleropyrrolidines Bearing π-Conjugated Moiety for Polymer Solar Cells: Contribution of the Chromophoric Substituent on C 60 to the Photocurrent
journal, November 2012

  • Saravanan, Chinnusamy; Liu, Che-Liang; Chang, Yi-Min
  • ACS Applied Materials & Interfaces, Vol. 4, Issue 11
  • DOI: 10.1021/am301773t

Electrochemistry of Fullerenes and Their Derivatives
journal, September 1998

  • Echegoyen, Luis; Echegoyen, Lourdes E.
  • Accounts of Chemical Research, Vol. 31, Issue 9, p. 593-601
  • DOI: 10.1021/ar970138v

Absolute Rate of Charge Separation and Recombination in a Molecular Model of the P3HT/PCBM Interface
journal, December 2010

  • Liu, Tao; Troisi, Alessandro
  • The Journal of Physical Chemistry C, Vol. 115, Issue 5
  • DOI: 10.1021/jp109130y

Conjugated poly(thiophenes): synthesis, functionalization, and applications
journal, June 1992

A Low Band Gap, Solution Processable Oligothiophene with a Diketopyrrolopyrrole Core for Use in Organic Solar Cells
journal, July 2008

  • Tamayo, Arnold B.; Walker, Bright; Nguyen*, Thuc-Quyen
  • The Journal of Physical Chemistry C, Vol. 112, Issue 30
  • DOI: 10.1021/jp8031572

Improved Purification of C60 and Formation of ?- and ?-Homoaromatic methano-bridged fullerenes by reaction with alkyl diazoacetates
journal, May 1993

  • Isaacs, Lyle; Wehrsig, Arno; Diederich, Fran�ois
  • Helvetica Chimica Acta, Vol. 76, Issue 3
  • DOI: 10.1002/hlca.19930760310

A novel complementary absorbing donor–acceptor pair in block copolymers based on single material organic photovoltaics
journal, January 2014

  • Koyuncu, Sermet; Wang, Hsin-Wei; Liu, Feng
  • J. Mater. Chem. A, Vol. 2, Issue 9
  • DOI: 10.1039/c3ta14902a

Fulleropyrrolidine-containing sterically hindered phenol. Synthesis, structure, and properties
journal, January 2001

  • Nuretdinov, I. A.; Gubskaya, V. P.; Yanilkin, V. V.
  • Russian Chemical Bulletin, Vol. 50, Issue 4, p. 607-613
  • DOI: 10.1023/A:1011392207814

Opening and Closure of the Fullerene Cage incis-Bisimino Adducts of C60: The Influence of the Addition Pattern and the Addend
journal, August 1996

  • Schick, Georg; Hirsch, Andreas; Mauser, Harald
  • Chemistry - A European Journal, Vol. 2, Issue 8
  • DOI: 10.1002/chem.19960020807

Synthesis of a rigid "ball-and-chain" donor-acceptor system through Diels-Alder functionalization of buckminsterfullerene (C60)
journal, June 1993

  • Khan, Saeed I.; Oliver, Anna M.; Paddon-Row, Michael N.
  • Journal of the American Chemical Society, Vol. 115, Issue 11
  • DOI: 10.1021/ja00064a075

Fullerene Bisadducts for Enhanced Open-Circuit Voltages and Efficiencies in Polymer Solar Cells
journal, June 2008

  • Lenes, Martijn; Wetzelaer, Gert-Jan A. H.; Kooistra, Floris B.
  • Advanced Materials, Vol. 20, Issue 11, p. 2116-2119
  • DOI: 10.1002/adma.200702438

Small Bandgap Polymers for Organic Solar Cells (Polymer Material Development in the Last 5 Years)
journal, August 2008

Hydrogen-bonded diketopyrrolopyrrole (DPP) pigments as organic semiconductors
journal, December 2014

  • Głowacki, Eric Daniel; Coskun, Halime; Blood-Forsythe, Martin A.
  • Organic Electronics, Vol. 15, Issue 12
  • DOI: 10.1016/j.orgel.2014.09.038

Observation of Both Thermal First-Order and Photochemical Zero-Order Kinetics in the Rearrangement of [6,5] Open Fulleroids to [6,6] Closed Fullerenes
journal, February 2001

  • Hall, Melvin H.; Lu, Huajun; Shevlin, Philip B.
  • Journal of the American Chemical Society, Vol. 123, Issue 7
  • DOI: 10.1021/ja003042w

A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu
journal, April 2010

  • Grimme, Stefan; Antony, Jens; Ehrlich, Stephan
  • The Journal of Chemical Physics, Vol. 132, Issue 15
  • DOI: 10.1063/1.3382344

Electron Trapping in Higher Adduct Fullerene-Based Solar Cells
journal, September 2009

  • Lenes, Martijn; Shelton, Steve W.; Sieval, Alex B.
  • Advanced Functional Materials, Vol. 19, Issue 18
  • DOI: 10.1002/adfm.200900459

Why Is the Rearrangement of [6,5] Open Fulleroids to [6,6] Closed Fullerenes Zero Order?
journal, February 1997

  • Li, Zizhong; Shevlin, Philip B.
  • Journal of the American Chemical Society, Vol. 119, Issue 5
  • DOI: 10.1021/ja963088i

Fulleropyrrolidines:  A Family of Full-Fledged Fullerene Derivatives
journal, September 1998

  • Prato, Maurizio; Maggini, Michele
  • Accounts of Chemical Research, Vol. 31, Issue 9
  • DOI: 10.1021/ar970210p

Generalized Gradient Approximation Made Simple [Phys. Rev. Lett. 77, 3865 (1996)]
journal, February 1997

Effects of Fullerene Bisadduct Regioisomers on Photovoltaic Performance
journal, July 2013

  • Meng, Xiangyue; Zhao, Guangyao; Xu, Qi
  • Advanced Functional Materials, Vol. 24, Issue 1
  • DOI: 10.1002/adfm.201301411

Energetic preference in 5,6 and 6,6 ring junction adducts of C60: fulleroids and methanofullerenes
journal, September 1993

  • Prato, Maurizio; Lucchini, Vittorio; Maggini, Michele
  • Journal of the American Chemical Society, Vol. 115, Issue 18
  • DOI: 10.1021/ja00071a080

A renaissance of color: New structures and building blocks for organic electronics
journal, January 2013

  • Robb, Maxwell J.; Ku, Sung-Yu; Brunetti, Fulvio G.
  • Journal of Polymer Science Part A: Polymer Chemistry, Vol. 51, Issue 6
  • DOI: 10.1002/pola.26531

A low band gap, solution processable oligothiophene with a dialkylated diketopyrrolopyrrole chromophore for use in bulk heterojunction solar cells
journal, March 2009

  • Tamayo, Arnold Bernarte; Dang, Xuan-Dang; Walker, Bright
  • Applied Physics Letters, Vol. 94, Issue 10
  • DOI: 10.1063/1.3086897

Investigation of photoexcitations of conjugated polymer/fullerene composites embedded in conventional polymers
journal, July 1998

  • Brabec, C. J.; Dyakonov, V.; Sariciftci, N. S.
  • The Journal of Chemical Physics, Vol. 109, Issue 3
  • DOI: 10.1063/1.476664

The Specific Acid-Catalyzed and Photochemical Isomerization of a Robust Fulleroid to a Methanofullerene
journal, April 1995

  • Gonzalez, Rosario; Hummelen, Jan C.; Wudl, Fred
  • The Journal of Organic Chemistry, Vol. 60, Issue 8
  • DOI: 10.1021/jo00113a049

Synthesis of Novel Acceptor Molecules of Mono- and Multiadduct Fullerene Derivatives for Improving Photovoltaic Performance
journal, January 2013

  • Liu, Chao; Xu, Liang; Chi, Dan
  • ACS Applied Materials & Interfaces, Vol. 5, Issue 3
  • DOI: 10.1021/am3028475

Origin of the Open Circuit Voltage of Plastic Solar Cells
journal, October 2001

Observation of a photoinduced electron transfer from a conducting polymer (MEHPPV) onto C60
journal, April 1993

DFT Calculations on Charge-Transfer States of a Carotenoid-Porphyrin-C 60 Molecular Triad
journal, March 2009

  • Baruah, Tunna; Pederson, Mark R.
  • Journal of Chemical Theory and Computation, Vol. 5, Issue 4
  • DOI: 10.1021/ct900024f

Efficient Methano[70]fullerene/MDMO-PPV Bulk Heterojunction Photovoltaic Cells
journal, July 2003

  • Wienk, Martijn M.; Kroon, Jan M.; Verhees, Wiljan J. H.
  • Angewandte Chemie International Edition, Vol. 42, Issue 29
  • DOI: 10.1002/anie.200351647

Solution processable low bandgap diketopyrrolopyrrole (DPP) based derivatives: novel acceptors for organic solar cells
journal, January 2010

  • Sonar, Prashant; Ng, Ging-Meng; Lin, Ting Ting
  • Journal of Materials Chemistry, Vol. 20, Issue 18
  • DOI: 10.1039/b924404b

Charge transfer excited state energies by perturbative delta self consistent field method
journal, August 2012

  • Baruah, Tunna; Olguin, Marco; Zope, Rajendra R.
  • The Journal of Chemical Physics, Vol. 137, Issue 8
  • DOI: 10.1063/1.4739269

Infrared intensities and Raman-scattering activities within density-functional theory
journal, September 1996

[6-6]-Closed versus [6-5]-Open Isomers of Imino- and Methanofullerenes:  A Comparison with Pristine C 60 and (C 59 N) •
journal, September 2000

  • Guldi, Dirk M.; Hungerbühler, Hartmut; Carmichael, Ian
  • The Journal of Physical Chemistry A, Vol. 104, Issue 38
  • DOI: 10.1021/jp0016838

Photoinduced Electron Transfer from a Conducting Polymer to Buckminsterfullerene
journal, November 1992

Organic Photovoltaics
book, January 2003

  • Brabec, Christoph J.; Dyakonov, Vladimir; Parisi, Jürgen
  • Springer Series in Materials Science
  • DOI: 10.1007/978-3-662-05187-0

On the Non‐Orthogonality Problem Connected with the Use of Atomic Wave Functions in the Theory of Molecules and Crystals
journal, March 1950

  • Löwdin, Per‐Olov
  • The Journal of Chemical Physics, Vol. 18, Issue 3
  • DOI: 10.1063/1.1747632

Photochemical Fulleroid to Methanofullerene Conversion via the Di-.pi.-methane (Zimmerman) Rearrangement
journal, January 1995

  • Janssen, Rene A. J.; Hummelen, Jan C.; Wudl, Fred
  • Journal of the American Chemical Society, Vol. 117, Issue 1
  • DOI: 10.1021/ja00106a068
    Sort by:
    [ × clear filter / sort ]

    Similar Records in DOE PAGES and OSTI.GOV collections: