Rational Design of Dithienopicenocarbazole-Based Dyes and a Prediction of Their Energy-Conversion Efficiency Characteristics for Dye-Sensitized Solar Cells

Yang, Zhenqing; Liu, Chunmeng; Li, Kuan; Cole, Jacqueline M.; Shao, Changjin; Cao, Dapeng

doi:10.1021/acsaem.7b00154

Rational Design of Dithienopicenocarbazole-Based Dyes and a Prediction of Their Energy-Conversion Efficiency Characteristics for Dye-Sensitized Solar Cells

Journal Article · Tue Mar 13 00:00:00 EDT 2018 · ACS Applied Energy Materials

DOI:https://doi.org/10.1021/acsaem.7b00154· OSTI ID:1491748

^[1]; Liu, Chunmeng ^[2]; Li, Kuan ^[2]; ^[3]; Shao, Changjin ^[2]; ^[4]

China Univ. of Petroleum, Beijing (People's Republic of China); Univ. of Cambridge, Cambridge (United Kingdom)
China Univ. of Petroleum, Beijing (People's Republic of China)
Univ. of Cambridge, Cambridge (United Kingdom); Rutherford Appleton Lab., Oxfordshire (United Kingdom); Argonne National Lab. (ANL), Argonne, IL (United States)
Beijing Univ. of Chemical Technology, Beijing (People's Republic of China)

Here, a series of metal-free organic donor-acceptor (D-A) derivatives (ME01-ME06) of the known dye C281 were designed using first principles calculations in order to evaluate their potential for applications in dye-sensitized solar cells (DSSCs). Their physical and electronic properties were calculated using density functional theory (DFT) and time-dependent density functional theory (TD-DFT). These include molecular properties that are required to assess the feasibility of a dye to function in DSSCs: UV/vis absorption spectra, light-harvesting efficiency (LHE), and driving forces of electron injection (ΔG_inj). ME01, ME02, and ME04 are predicted to exhibit broad absorption optical spectra that cover the entire visible range, rendering these three dyes promising DSSC prospects. Device-relevant calculations on these three short-listed dyes and the parent dye C281 were then performed, whereupon the dye molecules were adsorbed onto anatase TiO₂ surfaces to form the DSSC working electrode. Associated DSSC device characteristics of this dye…TiO₂ interfacial structure were determined. These include the light-harvesting efficiency, the number of injected electrons, the electron-injection lifetime, and the quantum energy alignment of the adsorbed dye molecule to that of its device components. In turn, these calculated parameters enabled the derivation of the DSSC device performance parameters: short-circuit current density, J_SC, incident photon-to-electron conversion efficiency, IPCE, and open-circuit voltage, V_OC. Thus, we demonstrate a systematic ab initio approach to screen rationally designed D-A dyes with respect to their potential applicability in high-performance DSSC devices.

View Accepted Manuscript (DOE)

Research Organization:: Argonne National Lab. (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1491748

Journal Information:: ACS Applied Energy Materials, Journal Name: ACS Applied Energy Materials Journal Issue: 4 Vol. 1; ISSN 2574-0962

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

References (56)

Perylene Imides for Organic Photovoltaics: Yesterday, Today, and Tomorrow Li, Chen; Wonneberger, Henrike Advanced Materials, Vol. 24, Issue 5 https://doi.org/10.1002/adma.201104447	journal	January 2012
Metal-Free Organic Dyes for Dye-Sensitized Solar Cells: From Structure: Property Relationships to Design Rules Mishra, Amaresh; Fischer, Markus K. R.; Bäuerle, Peter Angewandte Chemie International Edition, Vol. 48, Issue 14 https://doi.org/10.1002/anie.200804709	journal	March 2009
Low-dimensional variable range hopping in conducting polymers Epstein, A. J.; Lee, W. -P.; Prigodin, V. N. Synthetic Metals, Vol. 117, Issue 1-3 https://doi.org/10.1016/S0379-6779(00)00531-2	journal	February 2001
Charge transport in doped polythiophene Reedijk, J. A.; Martens, H. C. F.; van Bohemen, S. M. C. Synthetic Metals, Vol. 101, Issue 1-3 https://doi.org/10.1016/S0379-6779(98)01231-4	journal	May 1999
Theoretical studies on the electronic structures and optical properties of star-shaped triazatruxene/heterofluorene co-polymers Zhang, Zi-Long; Zou, Lu-Yi; Ren, Ai-Min Dyes and Pigments, Vol. 96, Issue 2 https://doi.org/10.1016/j.dyepig.2012.08.020	journal	February 2013
Theoretical study on novel double donor-based dyes used in high efficient dye-sensitized solar cells: The application of TDDFT study to the electron injection process Jungsuttiwong, Siriporn; Tarsang, Ruangchai; Sudyoadsuk, Taweesak Organic Electronics, Vol. 14, Issue 3 https://doi.org/10.1016/j.orgel.2012.12.018	journal	March 2013
Computational Study on the Intramolecular Charge Separation of D-A-π-A Organic Sensitizers with Different Linker Groups Yang, Jing; Wang, Xingzhu; Yim, Wai-Leung The Journal of Physical Chemistry C, Vol. 119, Issue 47 https://doi.org/10.1021/acs.jpcc.5b09117	journal	November 2015
Photocurrent Enhancement by Multilayered Porphyrin Sensitizers in a Photoelectrochemical Cell Palomaki, Peter K. B.; Civic, Marissa R.; Dinolfo, Peter H. ACS Applied Materials & Interfaces, Vol. 5, Issue 15 https://doi.org/10.1021/am401923f	journal	July 2013
Anchoring Groups for Dye-Sensitized Solar Cells Zhang, Lei; Cole, Jacqueline M. ACS Applied Materials & Interfaces, Vol. 7, Issue 6 https://doi.org/10.1021/am507334m	journal	February 2015
Large π-Aromatic Molecules as Potential Sensitizers for Highly Efficient Dye-Sensitized Solar Cells Imahori, Hiroshi; Umeyama, Tomokazu; Ito, Seigo Accounts of Chemical Research, Vol. 42, Issue 11 https://doi.org/10.1021/ar900034t	journal	November 2009
B-Doped Graphene as an Electrochemically Superior Metal-Free Cathode Material As Compared to Pt over a Co(II)/Co(III) Electrolyte for Dye-Sensitized Solar Cell Jung, Sun-Min; Choi, In Taek; Lim, Kimin Chemistry of Materials, Vol. 26, Issue 11 https://doi.org/10.1021/cm5013119	journal	May 2014
Dye-Sensitized Solar Cells Hagfeldt, Anders; Boschloo, Gerrit; Sun, Licheng Chemical Reviews, Vol. 110, Issue 11 https://doi.org/10.1021/cr900356p	journal	November 2010
Absolute electronegativity and hardness: application to inorganic chemistry Pearson, Ralph G. Inorganic Chemistry, Vol. 27, Issue 4 https://doi.org/10.1021/ic00277a030	journal	February 1988
Solvent Effects on Charge Transfer Bands of Nitrogen-Centered Intervalence Compounds Nelsen, Stephen F.; Trieber, Dwight A.; Ismagilov, Rustem F. Journal of the American Chemical Society, Vol. 123, Issue 24 https://doi.org/10.1021/ja003436n	journal	June 2001
Hopping Transport in Conductive Heterocyclic Oligomers: Reorganization Energies and Substituent Effects Hutchison, Geoffrey R.; Ratner, Mark A.; Marks, Tobin J. Journal of the American Chemical Society, Vol. 127, Issue 7 https://doi.org/10.1021/ja0461421	journal	February 2005
Engineering Organic Sensitizers for Iodine-Free Dye-Sensitized Solar Cells: Red-Shifted Current Response Concomitant with Attenuated Charge Recombination Bai, Yu; Zhang, Jing; Zhou, Difei Journal of the American Chemical Society, Vol. 133, Issue 30 https://doi.org/10.1021/ja203708k	journal	August 2011
Estimation of Electron Transfer Parameters from AM1 Calculations Nelsen, Stephen F.; Blomgren, Fredrik The Journal of Organic Chemistry, Vol. 66, Issue 20 https://doi.org/10.1021/jo001705m	journal	August 2001
First Principles Design of Dye Molecules with Ullazine Donor for Dye Sensitized Solar Cells Feng, Jie; Jiao, Yang; Ma, Wei The Journal of Physical Chemistry C, Vol. 117, Issue 8 https://doi.org/10.1021/jp310504n	journal	February 2013
Predicting Energy Conversion Efficiency of Dye Solar Cells from First Principles Ma, Wei; Jiao, Yang; Meng, Sheng The Journal of Physical Chemistry C, Vol. 118, Issue 30 https://doi.org/10.1021/jp410982e	journal	January 2014
Theoretical Study on Photophysical Properties of Multifunctional Electroluminescent Molecules with Different π-Conjugated Bridges Zou, Lu Yi; Ren, Ai Min; Feng, Ji Kang The Journal of Physical Chemistry A, Vol. 112, Issue 47 https://doi.org/10.1021/jp8032462	journal	October 2008
A Combined Experimental and Computational Investigation of Anthracene Based Sensitizers for DSSC: Comparison of Cyanoacrylic and Malonic Acid Electron Withdrawing Groups Binding onto the TiO ₂ Anatase (101) Surface Srinivas, Kola; Yesudas, K.; Bhanuprakash, K. The Journal of Physical Chemistry C, Vol. 113, Issue 46 https://doi.org/10.1021/jp907498e	journal	October 2009
First-Principles Modeling of the Adsorption Geometry and Electronic Structure of Ru(II) Dyes on Extended TiO ₂ Substrates for Dye-Sensitized Solar Cell Applications De Angelis, Filippo; Fantacci, Simona; Selloni, Annabella The Journal of Physical Chemistry C, Vol. 114, Issue 13 https://doi.org/10.1021/jp911663k	journal	March 2010
Ultrafast Electron Injection: Implications for a Photoelectrochemical Cell Utilizing an Anthocyanin Dye-Sensitized TiO ₂ Nanocrystalline Electrode Cherepy, Nerine J.; Smestad, Greg P.; Grätzel, Michael The Journal of Physical Chemistry B, Vol. 101, Issue 45 https://doi.org/10.1021/jp972197w	journal	November 1997
How the Nature of Triphenylamine-Polyene Dyes in Dye-Sensitized Solar Cells Affects the Open-Circuit Voltage and Electron Lifetimes Marinado, Tannia; Nonomura, Kazuteru; Nissfolk, Jarl Langmuir, Vol. 26, Issue 4 https://doi.org/10.1021/la902897z	journal	February 2010
High Open-Circuit Voltage Solid-State Dye-Sensitized Solar Cells with Organic Dye Chen, Peter; Yum, Jun Ho; Angelis, Filippo De Nano Letters, Vol. 9, Issue 6, p. 2487-2492 https://doi.org/10.1021/nl901246g	journal	June 2009
N-Doped Graphene Nanoplatelets as Superior Metal-Free Counter Electrodes for Organic Dye-Sensitized Solar Cells Ju, Myung Jong; Kim, Jae Cheon; Choi, Hyun-Jung ACS Nano, Vol. 7, Issue 6 https://doi.org/10.1021/nn4009774	journal	May 2013
New Type of Organic Sensitizers with a Planar Amine Unit for Efficient Dye-Sensitized Solar Cells Do, Kwangseok; Kim, Duckhyun; Cho, Nara Organic Letters, Vol. 14, Issue 1 https://doi.org/10.1021/ol203012s	journal	December 2011
Photoelectrochemical cells Grätzel, Michael Nature, Vol. 414, Issue 6861 https://doi.org/10.1038/35104607	journal	November 2001
A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO₂ films O'Regan, Brian; Grätzel, Michael Nature, Vol. 353, Issue 6346, p. 737-740 https://doi.org/10.1038/353737a0	journal	October 1991
Dye-sensitized solar cells with 13% efficiency achieved through the molecular engineering of porphyrin sensitizers Mathew, Simon; Yella, Aswani; Gao, Peng Nature Chemistry, Vol. 6, Issue 3 https://doi.org/10.1038/nchem.1861	journal	February 2014
Rhodaninedyes for dye-sensitized solar cells : spectroscopy, energy levels and photovoltaic performance Marinado, Tannia; Hagberg, Daniel P.; Hedlund, Maria Phys. Chem. Chem. Phys., Vol. 11, Issue 1 https://doi.org/10.1039/B812154K	journal	January 2009
Sensitizer molecular structure-device efficiency relationship in dye sensitized solar cells Clifford, John N.; Martínez-Ferrero, Eugenia; Viterisi, Aurélien Chem. Soc. Rev., Vol. 40, Issue 3 https://doi.org/10.1039/B920664G	journal	January 2011
Organic sensitizers from D–π–A to D–A–π–A: effect of the internal electron-withdrawing units on molecular absorption, energy levels and photovoltaic performances Wu, Yongzhen; Zhu, Weihong Chem. Soc. Rev., Vol. 42, Issue 5 https://doi.org/10.1039/C2CS35346F	journal	January 2013
Dithienopicenocarbazole as the kernel module of low-energy-gap organic dyes for efficient conversion of sunlight to electricity Yao, Zhaoyang; Wu, Heng; Li, Yang Energy & Environmental Science, Vol. 8, Issue 11 https://doi.org/10.1039/C5EE02822A	journal	January 2015
Improved molecular architecture of D–π–A carbazole dyes: 9% PCE with a cobalt redox shuttle in dye sensitized solar cells Soni, Saurabh S.; Fadadu, Kishan B.; Vaghasiya, Jayraj V. Journal of Materials Chemistry A, Vol. 3, Issue 43 https://doi.org/10.1039/C5TA06548H	journal	January 2015
A novel organic chromophore for dye-sensitized nanostructured solar cells Hagberg, Daniel P.; Edvinsson, Tomas; Marinado, Tannia Chemical Communications, Issue 21 https://doi.org/10.1039/b603002e	journal	January 2006
The end of iodide? Cobalt complex redox shuttles in DSSCs Hamann, Thomas W. Dalton Transactions, Vol. 41, Issue 11 https://doi.org/10.1039/c2dt12362b	journal	January 2012
Recent developments in molecule-based organic materials for dye-sensitized solar cells Yen, Yung-Sheng; Chou, Hsien-Hsin; Chen, Yung-Chung Journal of Materials Chemistry, Vol. 22, Issue 18 https://doi.org/10.1039/c2jm30362k	journal	January 2012
Modeling charge recombination in dye-sensitized solar cells using first-principles electron dynamics: effects of structural modification Ma, Wei; Jiao, Yang; Meng, Sheng Physical Chemistry Chemical Physics, Vol. 15, Issue 40 https://doi.org/10.1039/c3cp52458b	journal	January 2013
Arylamine organic dyes for dye-sensitized solar cells Liang, Mao; Chen, Jun Chemical Society Reviews, Vol. 42, Issue 8 https://doi.org/10.1039/c3cs35372a	journal	January 2013
Design of high-efficiency organic dyes for titania solar cells based on the chromophoric core of cyclopentadithiophene-benzothiadiazole Zhang, Min; Wang, Yinglin; Xu, Mingfei Energy & Environmental Science, Vol. 6, Issue 10 https://doi.org/10.1039/c3ee42331j	journal	January 2013
On the Theory of Electron‐Transfer Reactions. VI. Unified Treatment for Homogeneous and Electrode Reactions Marcus, R. A. The Journal of Chemical Physics, Vol. 43, Issue 2 https://doi.org/10.1063/1.1696792	journal	July 1965
Density‐functional thermochemistry. III. The role of exact exchange Becke, Axel D. The Journal of Chemical Physics, Vol. 98, Issue 7, p. 5648-5652 https://doi.org/10.1063/1.464913	journal	April 1993
Perspective: Advances and challenges in treating van der Waals dispersion forces in density functional theory Klimeš, Jiří; Michaelides, Angelos The Journal of Chemical Physics, Vol. 137, Issue 12 https://doi.org/10.1063/1.4754130	journal	September 2012
"Special points for Brillouin-zone integrations"—a reply Pack, James D.; Monkhorst, Hendrik J. Physical Review B, Vol. 16, Issue 4 https://doi.org/10.1103/PhysRevB.16.1748	journal	August 1977
Ab initio molecular-dynamics simulation of the liquid-metal–amorphous-semiconductor transition in germanium Kresse, G.; Hafner, J. Physical Review B, Vol. 49, Issue 20, p. 14251-14269 https://doi.org/10.1103/PhysRevB.49.14251	journal	May 1994
Projector augmented-wave method Blöchl, P. E. Physical Review B, Vol. 50, Issue 24, p. 17953-17979 https://doi.org/10.1103/PhysRevB.50.17953	journal	December 1994
Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set Kresse, G.; Furthmüller, J. Physical Review B, Vol. 54, Issue 16, p. 11169-11186 https://doi.org/10.1103/PhysRevB.54.11169	journal	October 1996
Electron-energy-loss spectra and the structural stability of nickel oxide: An LSDA+U study Dudarev, S. L.; Botton, G. A.; Savrasov, S. Y. Physical Review B, Vol. 57, Issue 3, p. 1505-1509 https://doi.org/10.1103/PhysRevB.57.1505	journal	January 1998
From ultrasoft pseudopotentials to the projector augmented-wave method Kresse, G.; Joubert, D. Physical Review B, Vol. 59, Issue 3, p. 1758-1775 https://doi.org/10.1103/PhysRevB.59.1758	journal	January 1999
Improved adsorption energetics within density-functional theory using revised Perdew-Burke-Ernzerhof functionals Hammer, B.; Hansen, L. B.; Nørskov, J. K. Physical Review B, Vol. 59, Issue 11 https://doi.org/10.1103/PhysRevB.59.7413	journal	March 1999
Effect of on-site Coulomb repulsion term U on the band-gap states of the reduced rutile (110) Ti O 2 surface Calzado, Carmen J.; Hernández, Norge Cruz; Sanz, Javier Fdez. Physical Review B, Vol. 77, Issue 4 https://doi.org/10.1103/PhysRevB.77.045118	journal	January 2008
Polaronic effects in TiO 2 calculated by the HSE06 hybrid functional: Dopant passivation by carrier self-trapping Deák, Peter; Aradi, Bálint; Frauenheim, Thomas Physical Review B, Vol. 83, Issue 15 https://doi.org/10.1103/PhysRevB.83.155207	journal	April 2011
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
Electron transfer reactions in chemistry. Theory and experiment Marcus, Rudolph A. Reviews of Modern Physics, Vol. 65, Issue 3, p. 599-610 https://doi.org/10.1103/RevModPhys.65.599	journal	July 1993
Carbazole Dyes with Alkyl-functionalized Thiophenes for Dye-sensitized Solar Cells: Relation between Alkyl Chain Length and Photovoltaic Performance Uemura, Yu; Mori, Shogo; Hara, Kohjiro Chemistry Letters, Vol. 40, Issue 8 https://doi.org/10.1246/cl.2011.872	journal	August 2011

Cited By (2)

Electrochemical Polymerization-Fabricated Several Triphenylamine–Carbazolyl-Based Polymers with Improved Short-Circuit Current and High Adsorption Stability in Dye-Sensitized Solar Cells Wang, Gang; Liu, Zhenhua; Wang, Xiaobo ACS Omega, Vol. 4, Issue 12 https://doi.org/10.1021/acsomega.9b02101	journal	September 2019
Low‐Cost, High‐Efficiency, and Efficiency Predictable Small Molecule Organic Dyes with Bis(4‐styryl)phenyl Amino Donor for Dye‐Sensitized Solar Cells Ying, Xintong; Liu, Yifei; Ling, Li Solar RRL, Vol. 3, Issue 6 https://doi.org/10.1002/solr.201900066	journal	March 2019

Similar Records

Electronic Structure and Optical Properties of Designed Photo-Efficient Indoline-Based Dye-Sensitizers with D–A–π–A Framework

Journal Article · Thu Jan 17 19:00:00 EST 2019 · Journal of Physical Chemistry. C · OSTI ID:1598498

Dye Aggregation, Photostructural Reorganization and Multiple Concurrent Dye···TiO₂ Binding Modes in Dye-Sensitized Solar Cell Working Electrodes Containing Benzothiadiazole-Based Dye RK-1

Journal Article · Mon Dec 02 19:00:00 EST 2019 · ACS Applied Energy Materials · OSTI ID:1606546

Triphenylamine based organic dyes for dye sensitized solar cells: A theoretical approach

Journal Article · Mon May 23 00:00:00 EDT 2016 · AIP Conference Proceedings · OSTI ID:22608759

Related Subjects

14 SOLAR ENERGY
DFT/TD-DFT
Metal-free organic dyes
absorption spectrum
donor-acceptor (D-A)
dye-sensitized solar cells

Rational Design of Dithienopicenocarbazole-Based Dyes and a Prediction of Their Energy-Conversion Efficiency Characteristics for Dye-Sensitized Solar Cells

Citation Formats

References (56)

Cited By (2)

Similar Records

Related Subjects