Designing Potential Donor Materials Based on DRCN5T with Halogen Substitutions: A DFT/TDDFT Study
Abstract
:1. Introduction
- (1)
- To investigate the effects of different halogen substitutions and the extent of halogenation on the photovoltaic properties of DRCN5T.
- (2)
- To find new promising donors (if possible) based on DRCN5T.
2. Results and Discussion
2.1. Benchmark Calculations
2.2. Dipole Moments of the Halogenated Molecules
2.3. LUMO/HOMO Energy and Energy Gap of the Halogenated Molecules
2.4. VOC of the OSC with Halogenated Molecules as Donors
2.5. Inner Reorganization Energy
2.6. Exciton Binding Energy of the Nine Halogenated Molecules
2.7. Singlet–Triplet Energy Gap of the Nine Halogenated Molecules
2.8. ESP of the Nine New Molecules
2.9. UV–Vis Spectra of the Designed New Molecules
3. Methods
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
- Liu, Y.S.; Zhou, J.Y.; Wan, X.J.; Chen, Y.S. Synthesis and Properties of Acceptor-Donor-Acceptor Molecules Based on Oligothiophenes with Tunable and Low Band Gap. Tetrahedron 2009, 65, 5209–5215. [Google Scholar] [CrossRef]
- Liu, Y.S.; Wan, X.J.; Wang, F.; Zhou, J.Y.; Long, G.K.; Tian, J.G.; Chen, Y.S. High-Performance Solar Cells Using a Solution-Processed Small Molecule Containing Benzodithiophene Unit. Adv. Mater. 2011, 23, 5387–5391. [Google Scholar] [CrossRef]
- Lin, Y.Z.; Li, Y.F.; Zhan, X.W. Small Molecule Semiconductors for High-Efficiency Organic Photovoltaics. Chem. Soc. Rev. 2012, 41, 4245–4272. [Google Scholar] [CrossRef]
- Zhang, L.; Colella, N.S.; Cherniawski, B.P.; Mannsfeld, S.C.B.; Briseno, A.L. Oligothiophene Semiconductors: Synthesis, Characterization, and Applications for Organic Devices. ACS Appl. Mater. Interfaces 2014, 6, 5327–5343. [Google Scholar] [CrossRef]
- Fitzner, R.; Mena-Osteritz, E.; Mishra, A.; Schulz, G.; Reinold, E.; Weil, M.; Körner, C.; Ziehlke, H.; Elschner, C.; Leo, K.; et al. Correlation of Pi-Conjugated Oligomer Structure with Film Morphology and Organic Solar Cell Performance. J. Am. Chem. Soc. 2012, 134, 11064–11067. [Google Scholar] [CrossRef] [PubMed]
- Zhang, Q.; Kan, B.; Liu, F.; Long, G.; Wan, X.; Chen, X.; Zuo, Y.; Ni, W.; Zhang, H.; Li, M.; et al. Small-Molecule Solar Cells with Efficiency over 9%. Nat. Photonics 2015, 9, 35–41. [Google Scholar] [CrossRef]
- Kan, B.; Li, M.; Zhang, Q.; Liu, F.; Wan, X.; Wang, Y.; Ni, W.; Long, G.; Yang, X.; Feng, H.; et al. A Series of Simple Oligomer-like Small Molecules Based on Oligothiophenes for Solution-Processed Solar Cells with High Efficiency. J. Am. Chem. Soc. 2015, 137, 3886–3893. [Google Scholar] [CrossRef]
- Ye, L.; Zhang, S.Q.; Huo, L.J.; Zhang, M.J.; Hou, J.H. Molecular Design toward Highly Efficient Photovoltaic Polymers Based on Two-Dimensional Conjugated Benzodithiophene. Acc. Chem. Res. 2014, 47, 1595–1603. [Google Scholar] [CrossRef] [PubMed]
- Li, W.; Albrecht, S.; Yang, L.; Roland, S.; Tumbleston, J.R.; McAfee, T.; Yan, L.; Kelly, M.A.; Ade, H.; Neher, D.; et al. Mobility-Controlled Performance of Thick Solar Cells Based on Fluorinated Copolymers. J. Am. Chem. Soc. 2014, 136, 15566–15576. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Ni, W.; Wan, X.J.; Li, M.M.; Wang, Y.C.; Chen, Y.S. A-D-A Small Molecules for Solution-Processed Organic Photovoltaic Cells. Chem. Commun. 2015, 51, 4936–4950. [Google Scholar] [CrossRef]
- Liu, P.; Zhang, K.; Liu, F.; Jin, Y.C.; Liu, S.J.; Russell, T.P.; Yip, H.L.; Huang, F.; Cao, Y. Effect of Fluorine Content in Thienothiophene-Benzodithiophene Copolymers on the Morphology and Performance of Polymer Solar Cells. Chem. Mat. 2014, 26, 3009–3017. [Google Scholar] [CrossRef]
- Min, J.; Zhang, Z.-G.; Zhang, S.; Li, Y. Conjugated Side-Chain-Isolated D–A Copolymers Based on Benzo[1,2-b:4,5-b′]dithiophene-alt-dithienylbenzotriazole: Synthesis and Photovoltaic Properties. Chem. Mat. 2012, 24, 3247–3254. [Google Scholar] [CrossRef]
- Liu, X.R.; Shen, W.; He, R.X.; Luo, Y.F.; Li, M. Strategy to Modulate the Electron-Rich Units in Donor-Acceptor Copolymers for Improvements of Organic Photovoltaics. J. Phys. Chem. C 2014, 118, 17266–17278. [Google Scholar] [CrossRef]
- Peet, J.; Senatore, M.L.; Heeger, A.J.; Bazan, G.C. The Role of Processing in the Fabrication and Optimization of Plastic Solar Cells. Adv. Mater. 2009, 21, 1521–1527. [Google Scholar] [CrossRef]
- Zhang, M.; Xu, X.; Yu, L.; Peng, Q. Efficient Wide-band-gap Copolymer Donors for Organic Solar Cells with Perpendicularly Placed Benzodithiophene Units. J. Power Sources 2021, 499, 229961. [Google Scholar] [CrossRef]
- Chen, H.; Hu, D.; Yang, Q.; Gao, J.; Fu, J.; Yang, K.; He, H.; Chen, S.; Kan, Z.; Duan, T.; et al. All-Small-Molecule Organic Solar Cells with an Ordered Liquid Crystalline Donor. Joule 2019, 3, 3034–3047. [Google Scholar] [CrossRef]
- Babics, M.; Duan, T.; Balawi, A.H.; Liang, R.; Cruciani, F.; Carja, I.; Gottlieb, D.; McCulloch, I.; Vandewal, K.; Laquai, F.; et al. Negligible Energy Loss During Charge Generation in Small-Molecule/Fullerene Bulk-Heterojunction Solar Cells Leads to Open-Circuit Voltage over 1.10 V. ACS Appl. Energy Mater. 2019, 2, 2717–2722. [Google Scholar] [CrossRef]
- Duan, T.; Gao, J.; Babics, M.; Kan, Z.; Zhong, C.; Singh, R.; Yu, D.; Lee, J.; Xiao, Z.; Lu, S. Difluorinated Oligothiophenes for High-Efficiency All-Small-Molecule Organic Solar Cells: Positional Isomeric Effect of Fluorine Substitution on Performance Variations. Sol. RRL 2020, 4, 1900472. [Google Scholar] [CrossRef]
- Qiu, W.; Zheng, S. Designing and Screening High-Performance Non-Fullerene Acceptors: A Theoretical Exploration of Modified Y6. Sol. RRL 2021, 5, 2100023. [Google Scholar] [CrossRef]
- Marin-Beloqui, J.; Toolan, D.; Panjwani, N.; Limbu, S.; Kim, J.; Clarke, T.M. Triplet-Charge Annihilation in a Small Molecule Donor: Acceptor Blend as a Major Loss Mechanism in Organic Photovoltaics. Adv. Energy Mater. 2021, 11, 2100539. [Google Scholar] [CrossRef]
- Li, G.; Zheng, S. A Computational Study of the Effects of Axial Halogen Substitutions of Boron Subphthalocyanines on their Electronic Spectra in Solution and in the Solid State. Spectrochim Acta A 2019, 222, 117180. [Google Scholar] [CrossRef] [PubMed]
- Xu, B.; Yi, X.; Huang, T.; Zheng, Z.; Zhang, J.; Salehi, A.; Coropceanu, V.; Hoi Yi Ho, C.; Marder, S.R.; Toney, M.F.; et al. Donor Conjugated Polymers with Polar Side Chain Groups: The Role of Dielectric Constant and Energetic Disorder on Photovoltaic Performance. Adv. Funct. Mater. 2018, 28, 1803418. [Google Scholar] [CrossRef]
- Sciuto, G.L.; Capizzi, G.; Salvatore, C.O.C.O.; Shikler, R. Geometric Shape Optimization of Organic Solar Cells for Efficiency Enhancement by Neural Networks. In Advances on Mechanics, Design Engineering and Manufacturing; Springer: Cham, Switzerland, 2017; pp. 789–796. [Google Scholar]
- Capizzi, G.; Lo Sciuto, G.; Napoli, C.; Shikler, R.; Woźniak, M. Optimizing the Organic Solar Cell Manufacturing Process by Means of AFM Measurements and Neural Networks. Energies 2018, 11, 1221. [Google Scholar] [CrossRef] [Green Version]
- Xu, X.; Zheng, S. Designing New Donor Materials Based on Functionalized DCCnT with Different Electron-Donating Groups: A Density Functional Theory (DFT) and Time Dependent Density Functional Theory (TDDFT)-Based Study. Int. J. Quantum Chem. 2019, 120, e26112. [Google Scholar] [CrossRef]
- Scharber, M.C.; Wuhlbacher, D.; Koppe, M.; Denk, P.; Waldauf, C.; Heeger, A.J.; Brabec, C.L. Design Rules for Donors in Bulk-Heterojunction Solar Cells—Towards 10% Energy-Conversion Efficiency. Adv. Mater. 2006, 18, 789–794. [Google Scholar] [CrossRef]
- Pablo-Pedro, R.; Lopez-Rios, H.; Mendoza-Cortes, J.; Kong, J.; Fomine, S.; Van Voorhis, T.; Dresselhaus, M. Exploring Low Internal Reorganization Energies for Silicene Nanoclusters. Phys. Rev. Appl. 2018, 9, 054012. [Google Scholar] [CrossRef] [Green Version]
- Xu, C.; Xu, X.; Zheng, S. On the Relations between Backbone Thiophene Functionalization and Charge Carrier Mobility of A–D–A type Small Molecules. New J. Chem. 2020, 44, 15177–15185. [Google Scholar] [CrossRef]
- Kraner, S.; Prampolini, G.; Cuniberti, G. Exciton Binding Energy in Molecular Triads. J. Phys. Chem. C 2017, 121, 17088–17095. [Google Scholar] [CrossRef]
- Han, G.; Hu, T.; Yi, Y. Reducing the Singlet−Triplet Energy Gap by End-Group π−π Stacking Toward High-Efficiency Organic Photovoltaics. Adv. Mater. 2020, 32, 2000975. [Google Scholar] [CrossRef] [PubMed]
- Benatto, L.; de Almeida Sousa, K.R.; Koehler, M. Driving Force for Exciton Dissociation in Organic Solar Cells: The Influence of Donor and Acceptor Relative Orientation. J. Phys. Chem. C 2020, 124, 13580–13591. [Google Scholar] [CrossRef]
- Yao, H.; Cui, Y.; Qian, D.; Ponseca, C.S., Jr.; Honarfar, A.; Xu, Y.; Xin, J.; Chen, Z.; Hong, L.; Gao, B.; et al. 14.7% Efficiency Organic Photovoltaic Cells Enabled by Active Materials with a Large Electrostatic Potential Difference. J. Am. Chem. Soc. 2019, 141, 7743–7750. [Google Scholar] [CrossRef]
- Xu, Y.; Yao, H.; Ma, L.; Hong, L.; Li, J.; Liao, Q.; Zu, Y.; Wang, J.; Gao, M.; Ye, L.; et al. Tuning the Hybridization of Local Exciton and Charge-Transfer States in Highly Efficient Organic Photovoltaic Cells. Angew. Chem. Int. Ed. 2020, 59, 9004–9010. [Google Scholar] [CrossRef]
- Dennington, R.K.T.; Millam, J. GaussView, Version 5; Semichem Inc.: Shawnee Mission, KS, USA, 2009. [Google Scholar]
- Frisch, M.J. Gaussian 2009 Revision D.01; Gaussian Inc.: Wallingford, CT, USA, 2009. [Google Scholar]
- Jacobson, L.D.; Herbert, J.M. Polarization-Bound Quasi-Continuum States Are Responsible for the “Blue Tail” in the Optical Absorption Spectrum of the Aqueous Electron. J. Am. Chem. Soc. 2010, 132, 10000–10002. [Google Scholar] [CrossRef]
- Zheng, S.; Geva, E.; Dunietz, B.D. Solvated Charge Transfer States of Functionalized Anthracene and Tetracyanoethylene Dimers: A Computational Study Based on a Range Separated Hybrid Functional and Charge Constrained Self-Consistent Field with Switching Gaussian Polarized Continuum Models. J. Chem. Theory Comput. 2013, 9, 1125–1131. [Google Scholar] [CrossRef]
- Stephens, P.J.; Devlin, F.J.; Chabalowski, C.F.; Frisch, M.J. Ab-Initio Calculation of Vibrational Absorption and Circular-Dichroism Spectra Using Density-Functional Force-Fields. J. Phys. Chem. 1994, 98, 11623–11627. [Google Scholar] [CrossRef]
- Hehre, W.J.; Ditchfield, R.; Pople, J.A. Self-Consistent Molecular-Orbital Methods XII. Further Extensions of Gaussian-Type Basis Sets for Use in Molecular-Orbital Studies of Organic-Molecules. J. Chem. Phys. 1972, 56, 2257–2261. [Google Scholar] [CrossRef]
- Xiao, M.; Tian, Y.; Zheng, S. An Insight into the Relationship between Morphology and Open Circuit Voltage/Electronic Absorption Spectrum at Donor-Acceptor Interface in Boron Subphthalocyanine Chloride/C70 Solar Cell: A DFT/TDDFT Exploration. Org. Electron. 2018, 59, 279–287. [Google Scholar] [CrossRef]
- Elsayed, S.A.; El-Gharabawy, H.M.; Butler, I.S.; Atlam, F.M. Novel Metal Complexes of 3-acetylcoumarin-2-hydrazinobenzothiazole Schiff Base: Design, Structural Characterizations, DNA Binding, DFT Calculations, Molecular Docking and Biological Studies. Appl. Organomet. Chem. 2020, 34, e5643. [Google Scholar] [CrossRef]
- McCarthy, M.; Lee, K.L.K. Molecule Identification with Rotational Spectroscopy and Probabilistic Deep Learning. J. Phys. Chem. A 2020, 124, 3002–3017. [Google Scholar] [CrossRef]
- Yanai, T.; Tew, D.P.; Handy, N.C. A New Hybrid Exchange–Correlation Functional Using the Coulomb-Attenuating Method (CAM-B3LYP). Chem. Phys. Lett. 2004, 393, 51–57. [Google Scholar] [CrossRef] [Green Version]
- Chai, J.D.; Head-Gordon, M. Long-Range Corrected Hybrid Density Functionals with Damped Atom-Atom Dispersion Corrections. Phys. Chem. Chem. Phys. 2008, 10, 6615–6620. [Google Scholar] [CrossRef] [Green Version]
- Phillips, H.; Zheng, Z.; Geva, E.; Dunietz, B.D. Orbital Gap Predictions for Rational Design of Organic Photovoltaic Materials. Org. Electron. 2014, 15, 1509–1520. [Google Scholar] [CrossRef]
- Sun, H.T.; Zhong, C.; Sun, Z.R. Recent Advances in the Optimally “Tuned” Range-Separated Density Functional Theory. Acta Phys. Chim. Sin. 2016, 32, 2197–2208. [Google Scholar] [CrossRef]
- Lu, T.; Chen, F. Multiwfn: A Multifunctional Wavefunction Analyzer. J. Comput. Chem. 2012, 33, 580–592. [Google Scholar] [CrossRef] [PubMed]
- Nelsen, S.F.; Blackstock, S.C.; Kim, Y. Estimation of Inner Shell Marcus Terms for Amino Nitrogen Compounds by Molecular Orbital Calculations. J. Am. Chem. Soc. 1987, 109, 677–682. [Google Scholar] [CrossRef]
- Lee, J.-C.; Chai, J.-D.; Lin, S.-T. Assessment of Density Functional Methods for Exciton Binding Energies and Related Optoelectronic Properties. RSC Adv. 2015, 5, 101370–101376. [Google Scholar] [CrossRef] [Green Version]
- Chen, X.; Zheng, S. On the Study of Influence of Molecular Arrangements and Dipole Moment on Exciton Binding Energy in Solid State. Int. J. Quantum Chem. 2020, 121, e26511. [Google Scholar] [CrossRef]
- Menke, S.M.; Sadhanala, A.; Nikolka, M.; Ran, N.A.; Ravva, M.K.; Abdel-Azeim, S.; Stern, H.L.; Wang, M.; Sirringhaus, H.; Thuc-Quyen, N.; et al. Limits for Recombination in a Low Energy Loss Organic Heterojunction. ACS Nano 2016, 10, 10736–10744. [Google Scholar] [CrossRef] [PubMed] [Green Version]
DRCN5T | Experiment | CAM-B3LYP | ωB97X | B3LYP | |
λmax (nm) | 531 | 589 | 688 | 766 | |
energy (eV) | 2.34 | 2.11 | 1.80 | 1.62 | |
DRCN5T2F | Experiment | CAM-B3LYP | ωB97X | B3LYP | |
λmax (nm) | 500 | 569 | 663 | 731 | |
energy (eV) | 2.48 | 2.18 | 1.87 | 1.70 |
DRCN-5T | DRCN-5T2F | DRCN-5T4F | DRCN-5T6F | DRCN-5T2Cl | DRCN-5T4Cl | DRCN-5T6Cl | DRCN-5T2Br | DRCN-5T4Br | DRCN-5T6Br | |
---|---|---|---|---|---|---|---|---|---|---|
HOMO | −6.43 | −6.57 | −6.74 | −6.90 | −7.22 | −7.65 | −7.78 | −7.04 | −7.73 | −7.81 |
LUMO | −2.49 | −2.53 | −2.57 | −2.69 | −2.34 | −2.24 | −2.36 | −2.25 | −2.21 | −2.34 |
IP correction | 0.80 | 0.79 | 0.80 | 0.83 | 0.79 | 0.81 | 0.85 | 0.79 | 0.79 | 0.87 |
EA correction | 0.50 | 0.49 | 0.47 | 0.44 | 0.72 | 0.50 | 0.49 | 0.72 | 0.52 | 0.51 |
VOC | 2.32 | 2.47 | 2.63 | 2.76 | 3.12 | 3.53 | 3.62 | 2.94 | 3.62 | 3.63 |
Cor VOC | 0.99 | 1.14 | 1.30 | 1.43 | 1.79 | 2.20 | 2.29 | 1.61 | 2.29 | 2.30 |
Exp VOC | 0.99 [7] | 1.12 [17] | N/A | N/A | N/A | N/A | N/A | N/A | N/A | N/A |
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. |
© 2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Share and Cite
Xiang, Y.; Zhang, J.; Zheng, S. Designing Potential Donor Materials Based on DRCN5T with Halogen Substitutions: A DFT/TDDFT Study. Int. J. Mol. Sci. 2021, 22, 13498. https://doi.org/10.3390/ijms222413498
Xiang Y, Zhang J, Zheng S. Designing Potential Donor Materials Based on DRCN5T with Halogen Substitutions: A DFT/TDDFT Study. International Journal of Molecular Sciences. 2021; 22(24):13498. https://doi.org/10.3390/ijms222413498
Chicago/Turabian StyleXiang, Yunjie, Jie Zhang, and Shaohui Zheng. 2021. "Designing Potential Donor Materials Based on DRCN5T with Halogen Substitutions: A DFT/TDDFT Study" International Journal of Molecular Sciences 22, no. 24: 13498. https://doi.org/10.3390/ijms222413498