Citation: Qian-Qian GAO, Qing-Tang YUAN, Xu-Feng SONG, Yan-Min YU, Jing GUO. Theoretical Study on Regulation of Photoelectric Properties of Zinc Porphyrin Dyes with Heterocyclopentadiene as π-Bridge[J]. Chinese Journal of Inorganic Chemistry, ;2022, 38(2): 295-303. doi: 10.11862/CJIC.2022.018 shu

Theoretical Study on Regulation of Photoelectric Properties of Zinc Porphyrin Dyes with Heterocyclopentadiene as π-Bridge

Beijing Key Laboratory for Green Catalysis and Separation, Department of Environmental Chemical Engineering, Beijing University of Technology, Beijing 100124, China

Corresponding author: Yan-Min YU, ymyu@bjut.edu.cn
Received Date: 11 August 2021
Revised Date: 18 November 2021

Figures(7)

To explore the regulation of photoelectric properties of zinc porphyrin dyes with heterocyclopentadiene as π-bridge, six new zinc porphyrin dyes were designed by introducing heterocyclopentadiene with different heteroatoms as the π-bridge based on the reference dye YD2-o-C8. The frontier molecular orbital energy levels, absorption spectra, and the hole-electron separation characteristics of the designed dyes were investigated using the density functional theory (DFT) and time-dependent density functional theory (TD-DFT) methods. The results show that compared with the reference dye YD2-o-C8, the introduction of heterocyclopentadiene in π-bridge can improve the photoelectric performance of dyes. The photoelectric properties of porphyrin dyes can be regulated by changing heteroatoms. Further analysis on the relationship between the properties of heterocyclopentadienes and the photoelectric performance of the porphyrin dyes shows that the lowest unoccupied molecular orbital energy level of heterocyclopentadienes has a good linear relationship with the photoelectric properties of the designed porphyrin dyes. The stronger electron receiving ability of heterocyclopentadiene can lead to the better performance of the porphyrin dye. The silicon-heterocyclopentadiene is of the strongest electron receiving ability, and the corresponding porphyrin dye has the widest absorption spectra and the strongest intramolecular charge transfer ability.
- porphyrin,
- dye,
- heterocyclopentadien,
- π-bridge,
- density functional theory
1. [1]
  Jiao S Z, Wen J Y, Zhou Y, Sun Z C, Liu Y Y, Liu R P. Preparation and Property Studies of Polyaniline Film for Flexible Counter Electrode of Dye-Sensitized Solar Cells by Cyclic Voltammetry[J]. ChemistrySelect, 2021,6(2):230-233. doi: 10.1002/slct.202004412
2. [2]
  Jiao S Z, Sun Z C, Wen J Y, Liu Y Y, Li F R, Miao Q Q, Wu W X, Li L H, Zhou Y. Development of Rapid Curing SiO₂ Aerogel Composite-Based Quasi Solid-State Dye-Sensitized Solar Cells through Screen-Printing Technology[J]. ACS Appl. Mater. Interfaces, 2020,12(43):48794-48803. doi: 10.1021/acsami.0c14551
3. [3]
  Grätzel M, O'regan B. A Low-Cost, High-Efficiency Solar-Cell Based on Dye-Sensitized Colloidal TiO₂ Films[J]. Nature, 1991,353(24):737-740.
4. [4]
  Zeng K W, Tong Z F, Ma L, Zhu W H, Wu W J, Xie Y S. Molecular Engineering Strategies for Fabricating Efficient Porphyrin-Based Dye-Sensitized Solar Cells[J]. Energy Environ. Sci., 2020,13:1617-1657. doi: 10.1039/C9EE04200H
5. [5]
  Urbani M, Grätzel M, Nazeeruddin M K, Torres T. Meso-Substituted Porphyrins for Dye-Sensitized Solar Cells[J]. Chem. Rev., 2014,114:12330-12396. doi: 10.1021/cr5001964
6. [6]
  Li L L, Diau E W G. Porphyrin-Sensitized Solar Cells[J]. Chem. Soc. Rev., 2013,42:291-304. doi: 10.1039/C2CS35257E
7. [7]
  Grätzel M, Kay A. Artificial Photosynthesis 1. Photosensitization of TiO₂ Solar Cells with Chlorophyll Derivatives and Related Natural Porphyrins[J]. J. Phys. Chem., 1993,97:6272-6277. doi: 10.1021/j100125a029
8. [8]
  Zhou H R, Ji J M, Kang S H, Kim M S, Lee H S, Kim C H, Kim H K. Molecular Design and Synthesis of D-π-A Structured Porphyrin Dyes with Various Acceptor Units for Dye-Sensitized Solar Cells[J]. J. Mater. Chem. C, 2019,7:2843-2852. doi: 10.1039/C8TC05283B
9. [9]
  Higashino T, Kurumisawa Y, Cai N, Fujimori Y, Tsuji Y, Nimura S, Packwood D M, Park J, Imahori H. A Hydroxamic Acid Anchoring Group for Durable Dye-Sensitized Solar Cells Incorporating a Cobalt Redox Shuttle[J]. ChemSusChem, 2017,10:3347-3351. doi: 10.1002/cssc.201701157
10. [10]
  Li C M, Luo L, Wu D, Jiang R Y, Lan J B, Wang R L, Huang L Y, Yang S Y, You J S. Porphyrins with Intense Absorptivity: Highly Efficient Sensitizers with a Photovoltaic Efficiency of Up to 10.7% without a Cosensitizer and a Coabsorbate[J]. J. Mater. Chem. A, 2016,4:11829-11834. doi: 10.1039/C6TA02888H
11. [11]
  Yella A, Lee H W, Tsao H N, Yi C, Chandiran A K, Nazeeruddin M K, Diau E W G, Yeh C Y, Zakeeruddin S M, Grätzel M. Porphyrin-Sensitized Solar Cells with Cobalt(Ⅱ/Ⅲ)-Based Redox Electrolyte Exceed 12 Percent Efficiency[J]. Science, 2011,334(6056):629-634. doi: 10.1126/science.1209688
12. [12]
  Luo J, Zhang J, Huang K W, Qi Q B, Dong S Q, Zhang J, Wang P, Wu J S. N-Annulated Perylene Substituted Zinc-Porphyrins with Different Linking Modes and Electron Acceptors for Dye Sensitized Solar Cells[J]. J. Mater. Chem. A, 2016,4:8428-8434. doi: 10.1039/C6TA02509A
13. [13]
  Sheng Y, Li M J, Flores-Leonar M M, Lu W C, Yang J, Hu Y N. Rational Design of SM315-Based Porphyrin Sensitizers for Highly Efficient Dye-Sensitized Solar Cells: A Theoretical Study[J]. J. Mol. Struct., 2020,1205:127567-127576. doi: 10.1016/j.molstruc.2019.127567
14. [14]
  Yuan Q T, Yu Y M, Sun Z C, Song X F. Enhancing the Photoelectric Properties of Zinc Porphyrin Dyes by Introducing Five-Membered Heterocyclic Rings into the Electron Donor: A Density Functional Theory and Time-Dependent Density Functional Theory Study[J]. ACS Omega, 2021,6(36):23551-23557. doi: 10.1021/acsomega.1c03635
15. [15]
  Kang S H, Jung S Y, Kim Y W, Eom Y K, Kim H K. Exploratory Synthesis and Photovoltaic Performance Comparison of D-π-A Structured Zn-Porphyrins for Dye-Sensitized Solar Cells[J]. Dyes Pigm., 2018,149:341-347. doi: 10.1016/j.dyepig.2017.10.011
16. [16]
  Zhang J, Chen C J, Zhu H C. Porphyrin Dyes Bearing Heterocyclic Anchoring Groups for Dye-Sensitized Solar Cells with Enhanced Efficiency and Long-Term Stability: Further Optimization of Champion Porphyrin Dye SM315[J]. Appl. Surf. Sci., 2020,513:145844-145852. doi: 10.1016/j.apsusc.2020.145844
17. [17]
  Kumar R S, Jeong H, Jeong J, Chitumalla R K, Ko M J, Kumar K S, Jang J, Son Y. Synthesis of Porphyrin Sensitizers with a Thiazole Group as an Efficient π-Spacer: Potential Application in Dye-Sensitized Solar Cells[J]. RSC Adv., 2016,6:41294-41303. doi: 10.1039/C6RA00353B
18. [18]
  Krishna J V S, Koteshwar D, Chowdhury T H, Singh S P, Bedja I, Islam A, Giribabu L. Efficient Near IR Porphyrins Containing a Triphenylamine-Substituted Anthryl Donating Group for Dye Sensitized Solar Cells[J]. J. Mater. Chem. C, 2019,7:13594-13605. doi: 10.1039/C9TC03943K
19. [19]
  Mathew S, Yella A, Gao P, Humphry-Baker R, Curchod B F E, Ashari-Astani N, Tavernelli I, Rothlisberger U, Nazeerunndin M K, Grätzel M. Dye-Sensitized Solar Cells with 13% Efficiency Achieved through the Molecular Engineering of Porphyrin Sensitizers[J]. Nat. Chem., 2014,6(3):242-247. doi: 10.1038/nchem.1861
20. [20]
  Li W, Ren W H, Chen Z, Lu T F, Deng L, Tang J F, Zhang X M, Wang L, Bai F Q. Theoretical Design of Porphyrin Dyes with Electron-Deficit Heterocycles towards Near-IR Light Sensitization in Dye-Sensitized Solar Cells[J]. Sol. Energy, 2019,188:742-749. doi: 10.1016/j.solener.2019.06.062
21. [21]
  Hu W X, Yu P, Zhang Z M, Shen W, Li M, He R X. Theoretical Study of YD2-o-C8-Based Derivatives as Promising Sensitizers for Dye-Sensitized Solar Cells[J]. J. Mater. Sci., 2017,52(3):1235-1245. doi: 10.1007/s10853-016-0364-z
22. [22]
  Jia H L, Ji X H, Zhang M D, Ju Z M, Zheng H G. Effects of Heterocycles Containing Different Atoms as π-Bridges on the Performance of Dye-Sensitized Solar Cells[J]. Phys. Chem. Chem. Phys., 2015,17:16334-16340. doi: 10.1039/C5CP02194D
23. [23]
  Cabau L, Kumar C V, Moncho A, Clifford J N, Lopez N, Palomares E. A Single Atom Change "Switches-On" the Solar-to-Energy Conversion Efficiency of Zn-Porphyrin Based Dye Sensitized Solar Cells to 105%[J]. Energy Environ. Sci., 2015,8:1368-1375. doi: 10.1039/C4EE03320E
24. [24]
  Krishna N V, Krishna J V S, Singh S P, Giribabu L, Han L Y, Bedja I, Gupta R K, Islam A. Donor-π-Acceptor Based Stable Porphyrin Sensitizers for Dye-Sensitized Solar Cells: Effect of π-Conjugated Spacers[J]. J. Phys. Chem. C, 2017,121:6464-6477. doi: 10.1021/acs.jpcc.6b12869
25. [25]
  Ding W L, Cui Y M, Yang L N, Li Q S, Li Z S. Rational Design of Near-Infrared Zn-Porphyrin Dye Utilized in Co-Sensitized Solar Cell toward High Efficiency[J]. Dyes Pigm., 2017,136:450-457. doi: 10.1016/j.dyepig.2016.09.002
26. [26]
  Jin X Y, Li D Y, Sun L B, Wang C L, Bai F Q. Theoretical Design of Porphyrin Sensitizers with Different Acceptors for Application in Dye Sensitized Solar Cells[J]. RSC Adv., 2018,8:19804-19810. doi: 10.1039/C8RA02974A
27. [27]
  Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Scalmani G, Barone V, Petersson G A, Nakatsuji H, Li X, Caricato M, Marenich A V, Bloino J, Janesko B G, Gomperts R, Mennucci B, Hratchian H P, Ortiz J V, Izmaylov A F, Sonnenberg J L, Williams-Young D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski V G, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery J A Jr, Peralta J E, Ogliaro F, Bearpark M J, Heyd J J, Brothers E N, Kudin K N, Staroverov V N, Keith T A, Kobayashi R, Normand J, Raghavachari K, Rendell A P, Burant J C, Iyengar S S, Tomasi J, Cossi M, Millam J M, Klene M, Adamo C, Cammi R, Ochterski J W, Martin R L, Morokuma K, Farkas O, Foresman J B, Fox D J. Gaussian 16, Revision A. 03., Gaussian, Inc., Wallingford CT, 2016.
28. [28]
  Becke A D. Density-Functional Thermochemistry. Ⅲ. The Role of Exact Exchange[J]. J. Chem. Phys., 1993,98(7):5648-5652. doi: 10.1063/1.464913
29. [29]
  Yanai T, Tew D P, Handy N C. A New Hybrid Exchange-Correlation Functional Using the Coulomb-Attenuating Method (CAMB3LYP)[J]. Chem. Phys. Lett., 2004,393:51-57. doi: 10.1016/j.cplett.2004.06.011
30. [30]
  Adamo C, Barone V. Toward Reliable Density Functional Methods without Adjustable Parameters: The PBE0 Mode[J]. J. Chem. Phys., 1999,110:6158-6170. doi: 10.1063/1.478522
31. [31]
  Zhao Y, Truhlar G. The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-Class Functionals and 12 Other Functionals[J]. Theor. Chem Acc., 2008,120:215-241. doi: 10.1007/s00214-007-0310-x
32. [32]
  Tomasi J, Mennucci B, Cammi R. Quantum Mechanical Continuum Solvation Models[J]. Chem. Rev., 2005,105:2999-3093. doi: 10.1021/cr9904009
33. [33]
  Lu T, Chen F W. Multiwfn: A Multifunctional Wavefunction Analyzer[J]. J. Comput. Chem., 2012,33:580-592. doi: 10.1002/jcc.22885
34. [34]
  Liu Z Y, Lu T, Chen Q X. An sp-Hybridized All-Carboatomic Ring, Cyclo[18]Carbon: Electronic Structure, Electronic Spectrum, and Optical Nonlinearity[J]. Carbon, 2020,165:461-467. doi: 10.1016/j.carbon.2020.05.023
35. [35]
  Le Bahers T, Adamo C, Ciofini I. A Qualitative Index of Spatial Extent in Charge-Transfer Excitations[J]. J. Chem. Theory Comput., 2011,7:2498-2506. doi: 10.1021/ct200308m
36. [36]
  Lu T. Multiwfn Manual, Version 3.8(dev), Section 3.21.1, http://sobereva.com/multiwfn
37. [37]
  Zhang G L, Bai Y, Li R Z, Shi D, Wenger S, Zakeeruddin S M, Grätzel M, Wang P. Employ A Bisthienothiophene Linker to Construct an Organic Chromophore for Efficient and Stable Dye-Sensitized Solar Cells[J]. Energy Environ. Sci., 2009,2:92-95. doi: 10.1039/B817990E
38. [38]
  Asbury J B, Wang Y Q, Hao E C, Ghosh H N, Lian T Q. Regio-Controlled Intramolecular Reductive Cyclization of Diynes[J]. Res. Chem. Intermed., 2001,27:393-406. doi: 10.1163/156856701104202255
39. [39]
  Zhang J, Li H B, Sun S L, Geng Y, Wu Y, Su Z M. Density Functional Theory Characterization and Design of High-Performance Diarylamine-Fluorene Dyes with Different π Spacers for Dye-Sensitized Solar Cells[J]. J. Mater. Chem., 2012,22:568-576. doi: 10.1039/C1JM13028E
40. [40]
  Khabashesku V N, Balaji V, Boganov S E, Nfedov O M, Michl J. Matrix Isolation of Silacyclopentadienes: UV-Vis and IR Spectra and Photochemical Interconversion[J]. J. Am. Chem. Soc., 1994,116:320-329. doi: 10.1021/ja00080a037
41. [41]
  Tamao K, Yamaguchi S. Regio-Controlled Intramolecular Reductive Cyclization of Diynes[J]. Pure Appl. Chem., 1996,68(1):139-144. doi: 10.1351/pac199668010139
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